- Regio- and diastereoselective vinylogous Mannich addition of 3-alkenyl-2-oxindoles to α-fluoroalkyl aldimines
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An efficient asymmetric vinylogous Mannich (AVM) addition reaction of 3-alkenyl-2-oxindoles to α-fluoroalkyl aldimines has been developed. This reaction provided various optical active α-alkylidene-δ-amino-δ-fluoroalkyl oxindoles in excellent yields, complete γ-site regioselectivity, and excellent diastereoselectivities.
- Liu, Yingle,Yang, Yi,Huang, Yangen,Xu, Xiu-Hua,Qing, Feng-Ling
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- Synthesis and bio-evaluation of quaternary centered 3-hydroxy-3-(trifluoromethyl)indolin-2-one derivatives for anticancer and antimicrobial activities
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Abstract: A series of C(3)-trifluoromethylated compounds derived from N-substituted isatins were synthesized. The biological activity of all 3-hydroxy-3-(trifluoromethyl)indolin-2-one derivatives have been evaluated for in vitro cytotoxic activity and antibacterial activity. The active compounds were screened against nuclear xenobiotic receptor CAR (PDB ID: 1XLS), PIM1 kinase (PDB ID: 2O65), and CDK2 kinase (PDB ID: 3QHR) by using in silico molecular docking studies to obtain lead molecules. In addition to its potential anticancer activity, 5-bromo-3-ethynyl-3-hydroxy-1-(prop-2-yn-1-yl)indolin-2-one also showed specific antibacterial activity against S. aureus. Graphical abstract: [Figure not available: see fulltext.]
- Bikshapathi, Raktani,Prathima, Parvathaneni Sai,Yashwanth,Pamanji,Jagadeeshkumar,Maheshwari,Rao, J. Venkateswara,Murty,Rao, V. Jayathirtha
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- Fluorous chiral bisoxazolines: Application in copper-catalyzed asymmetric α-hydrophosphonylation
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A copper-catalyzed asymmetric α-hydrophosphonylation of isatins with a novel fluorous bis(oxazoline) as a ligand is presented. The corresponding chiral α1-oxindole-α-hydroxyphosphonates were obtained in 30-91% yield with enantioselectivities up to 92%. The fluorous ligand can be easily recovered and reused at least 3 times without a significant loss in its activity. This journal is the Partner Organisations 2014.
- Deng, Tao,Wang, Hongjun,Cai, Chun
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- Synthesis and anticancer activity evaluation of azepinobisindoles;the isomeric iheyamine A-derivatives
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Azepinobisindole derivatives, the isomeric Iheyamine skeleton, were prepared and their anticancer activity evaluation were investigated against two human cancer cell lines, Hepatocellular carcinoma (HepG2) and human cervical cancer line (HeLa) as well as the normal cell line (Vero cell line) using MTT assay. The anticancer activity results indicated that 2-methoxy-5-methyl-5H-azepino[2,3-b:4,5-b]diindole was the most active derivative against tested cell lines. Additionally, molecular docking study in silico the possible inhibitory effect of cyclin-dependent kinase 2 (CDK2) by the azepinoindole revealed that all synthesized compounds fit well in the binding cavity of CDK2.
- Phutdhawong, Weerachai,Rattanopas, Sopita,Sirirak, Jitnapa,Taechowisan, Thongchai,Phutdhawong, Waya S.
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- Synthesis of Isatins through Direct Oxidation of Indoles with IBX-SO3K/NaI
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The direct conversion of indoles into isatins is presented. The reagent mixture NaI/IBX-SO3K, containing a sulfonylated derivative of 2-iodoxybenzoic acid, was employed to trigger this oxidative process. Moreover, the synthetic route toward IBX-SO3K and the X-ray crystal structure of the title compound are described in great detail.
- Bredenkamp, Angla,Mohr, Fabian,Kirsch, Stefan F.
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- Fluorinated alcohol-mediated [4 + 3] cycloaddition reaction of indolyl alcohols with cyclopentadiene
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This paper describes an efficient [4 + 3] cycloaddition reaction of 3-indolylmethanols with cyclopentadiene in hexafluoroisopropanol (HFIP), which is catalyst-free and inexpensive, and offers mild reaction conditions, wide substrate scope and convenient workup. This methodology provides the first catalyst- and additive-free [4 + 3] cycloaddition reactions of indolyl alcohols, offering a green and efficient method for the synthesis of cyclohepta[b]indole derivatives.
- Liu, Jian,Wang, Liang,Wang, Xiaoxiao,Xu, Lubin,Hao, Zhihui,Xiao, Jian
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- Water-Promoted Regiospecific Azidolysis and Copper-Catalyzed Azide-Alkyne Cycloaddition: One-Pot Synthesis of 3-Hydroxy-1-alkyl-3-[(4-aryl/alkyl-1H-1,2,3-triazol-1-yl)methyl]indolin-2-ones
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An efficient, eco-friendly, base free, one-pot, sequential protocol was developed for epoxide azidolysis and copper-catalyzed azide-alkyne cycloaddition using water as the solvent for the synthesis of 3-hydroxy-1-alkyl-3-[(4-aryl/alkyl-1H-1,2,3-triazol-1-yl)methyl]indolin-2-ones. The optimized reaction conditions have been generalized in the case of aromatic as well as aliphatic alkyne partners to afford good yields and high regioselectivity.
- Kumar, Kapil,Konar, Debabrata,Goyal, Sandeep,Gangar, Mukesh,Chouhan, Mangilal,Rawal, Ravindra K.,Nair, Vipin A.
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- Synthesis of Spiro[oxindole-3,2′-pyrrolidine] Derivatives from Benzynes and Azomethine Ylides through 1,3-Dipolar Cycloaddition Reactions
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A novel synthetic strategy employing benzyne and azomethine ylides for the construction of spiro[oxindole-3,2′-pyrrolidine] derivatives has been achieved in good yields. The ketimines obtained from the condensation of isatins with CF3CH2NH2 react with benzyne in the presence of weak bases such as TBAF or TBAT. This mild practical 1,3-dipolar cycloaddition provides an efficient route to access biologically active compounds.
- Ryu, Heesun,Seo, Jeongseob,Ko, Haye Min
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- Pushing the boundaries of vinylogous reactivity: Catalytic enantioselective Mukaiyama aldol reactions of highly unsaturated 2-silyloxyindoles
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The first example of catalytic, enantioselective hypervinylogous Mukaiyama aldol reaction (HVMAR) involving multiply unsaturated 2-silyloxyindoles is reported. The reaction utilizes a chiral Lewis base-catalyzed Lewis acid-mediated technology to deliver homoallylic 3-polyenylidene 2-oxindoles with extraordinary levels of regio-, enantio-, and geometrical selectivity. This work highlights a subtle yet decisive influence of the indole N-substituents on the propagation of the vinylogous reactivity space of the donor substrates up to ten bonds away from the origin of the vinylogy effect. Analysis of the 13C NMR chemical shifts of the C-ω remote site within homologous silyloxyindole donors enabled rationalization of the results and easy qualitative prediction of the HVMAR reactivity/inertia toward a given aldehyde acceptor.
- Curti, Claudio,Sartori, Andrea,Battistini, Lucia,Brindani, Nicoletta,Rassu, Gloria,Pelosi, Giorgio,Lodola, Alessio,Mor, Marco,Casiraghi, Giovanni,Zanardi, Franca
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- Synthesis and evaluation of in?vivo antioxidant, in?vitro antibacterial, MRSA and antifungal activity of novel substituted isatin N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazones
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Some new isatin N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazones 4a-t with different substituents at 1-, 5- and 7-positions of isatin ring have been synthesized by reaction of N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazide 2 with corresponding isatins 3a-t. Compounds 4a-t were evaluated in?vivo for antioxidant activity and in?vitro for anti-microorganism activities. The MIC values were found for Gram positive bacteria (MIC?=?1.56–6.25?μM), for Gram negative bacteria (MIC?=?12.5?μM), and for fungi Aspergillus niger (MIC?=?3.12–12.5?μM), Fusarium oxysporum (MIC?=?6.25–12.5?μM) and Saccharomyces cerevisiae (MIC?=?6.25–12.5?μM). Regarding the antioxidant activity, the SOD, GHS-Px and catalase activities of 4c-i and 4m-r were MIC?=?10.57–10.85, 0.27–0.93 and 345.45–399.75 unit/mg protein, respectively. Compounds 4e-h had MIC values of 0.78, 1.56, and 3.12?μM for three clinical MRSA isolates. Compound 4e showed the selective cytotoxic effects against some cancer (LU-1, HepG2, MCF7, P338, SW480, KB) cell lines and normal fibroblast cell line NIH/3T3.
- Thanh, Nguyen Dinh,Giang, Nguyen Thi Kim,Quyen, Tran Ha,Huong, Doan Thi,Toan, Vu Ngoc
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- Electrocatalytic C-H/N-H Coupling of 2′-Aminoacetophenones for the Synthesis of Isatins
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2′-Aminoacetophenones undergo a C(sp3)-H oxidation followed by intramolecular C-N bond formation by virtue of a simple electrochemical oxidation in the presence of n-Bu4NI, providing various isatins with moderate to good yields. The reaction intermediates were detected, and a radical-based pathway was proposed.
- Qian, Peng,Su, Ji-Hu,Wang, Yukang,Bi, Meixiang,Zha, Zhenggen,Wang, Zhiyong
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- Addition of carbamoylsilane to isatins: Highly efficient synthesis of 3-hydroxy-3-aminocarbonyl-2-oxindoles derivatives
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The first addition reaction between isatins and carbamoysilane has been developed which provides 3-hydroxy-3-aminocarbonyl-2-oxindoles core structures with excellent yields. Moreover, the reaction could undergo a one-pot synthesis process to furnish 3-hydroxy-3-aminocarbonyl-2-oxindole with gram-scale.
- Liang, Jin-Yan,Wang, Hui,Yang, Yan-Li,Shen, Shou-Jie,Chen, Jian-Xin
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- The aggregation-induced emission enhancement properties of BF2 complex isatin-phenylhydrazone: Synthesis and fluorescence characteristics
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Isatin-phenylhydrazone derivatives and their corresponding BF2 complexes were efficiently synthesised by a three-step reaction starting from isatin and phenylhydrazine hydrochloride. The fluorescence properties of the isatin-phenylhydrazone derivatives and derived BF2 complexes were investigated in different organic solvents, in the solid state and in mixed solvent solutions of THF and H2O. These fluorescent dyes exhibited low fluorescent intensity in solution but a high fluorescent intensity as aggregates and in their solid state due to the interesting aggregation-induced emission enhancement characteristics which were caused by the inhibition of intramolecular rotation in the single molecule state. Information supporting this inference was supported by single crystal X-ray analysis.
- Zheng, Jie,Huang, Fang,Li, Yujin,Xu, Tianwei,Xu, Hui,Jia, Jianhong,Ye, Qing,Gao, Jianrong
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- A facile one pot C[sbnd]C and C[sbnd]N bond formation for the synthesis of spiro-benzodiazepines and their cytotoxicity
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An efficient, multicomponent and environmentally benign protocol has been developed for the synthesis of spiro-benzodiazepines through C[sbnd]C and C[sbnd]N bond formations in a single step. This one-pot protocol proceeds via three component reaction of o
- Nagaraju, Burri,Kovvuri, Jeshma,Babu, K. Suresh,Adiyala, Praveen Reddy,Nayak, V. Lakshma,Alarifi, Abdullah,Kamal, Ahmed
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- A Highly Stereoselective Chiral Auxiliary-assisted Reductive Cyclization to Furoindoline
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Highly stereoselective furoindoline derivatives were synthesized by exploring the imidazolidinone-based chiral auxiliary-mediated aldol adduct. The one-pot reductive cyclization was achieved through NiCl2.6H2O/NaBH4.
- Kumar, Kapil,More, Shital S.,Khatik, Gopal L.,Rawal, Ravindra K.,Nair, Vipin A.
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- A facile one-pot method for the preparation of N-Alkyl isatins under microwave irradiation
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N-Alkyl isatins have been prepared by reaction of the isatin and 5-bromoisatin with K2CO3 and convenient alkyl halides in DMF under microwave irradiation with the high yield, simple work-up and short time.
- Azizian, Javad,Fallah-Bagher-Shaidaei, Hossain,Kefayati, Hassan
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- Enantio- And Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes
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We describe a strategy for the enantio- and diastereoselective synthesis of homoallylic α-trifluoromethyl amines by the catalytic hydroalkylation of terminal dienes. Trifluoromethyl-substituted isatin-derived azadienolate nucleophiles undergo γ-selective alkylation with a Pd-DTBM-SEGPHOS catalyst, which additionally promotes regioselective addition to the diene and delivers products in up to 86% yield, 10:1 dr, and 97.5:2.5 er.
- Onyeagusi, Chibueze I.,Shao, Xinxin,Malcolmson, Steven J.
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- Development of isatin-thiazolo[3,2-a]benzimidazole hybrids as novel CDK2 inhibitors with potent in vitro apoptotic anti-proliferative activity: Synthesis, biological and molecular dynamics investigations
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In the current medical era, human health is experiencing numerous challenges, particularly the human malignancies. Therefore, the therapeutic arsenal for these malignancies is to be inexorably enhanced with new treatments that target tumor cells in a selective manner. In this regard, the present work aims at developing a new set of small molecules featuring the privileged isatin scaffold conjugated with a thiazolo[3,2-a]benzimidazole (TBI) motif through a cleavable hydrazide linker (7a-e and 10a-i) as potential anticancer CDK2 inhibitors. The large tricyclic TBI motif is anticipated to achieve a plethora of hydrophobic interactions within the CDK2 binding site. The growth of the two examined cell lines was significantly inhibited by most the prepared hybrids with IC50 ranges; (2.60 ± 1.47–20.90 ± 1.17 μM, against MDA-MB-231) and (1.27 ± 0.06–16.83 ± 0.95 μM, against MCF-7). In particular, hybrids 7a, 7d and 10a displayed potent dual activity against the examined cell lines, and thus selected for further investigations. They exerted a significance alteration in the cell cycle progression, in addition to an apoptosis induction within both MDA-MB-231 and MCF-7 cells. Furthermore, 7a, 7d and 10a displayed potent CDK2 inhibitory action (IC50 = 96.46 ± 5.3, 26.24 ± 1.4 and 42.95 ± 2.3 nM, respectively). The docking simulations unveiled, as expected, the ability of the TBI ring to well-accommodate and establish several hydrophobic interactions within a hydrophobic pocket in the CDK2 binding site. Also, the docking simulations highlighted the significance of incorporation of the hydrazide linker and isatin unsubstituted (NH) functionality in the H-bonding interactions. Interestingly, the most potent CDK2 inhibitor 7d achieved the best binding score (-11.2 Kcal/mole) and formed the most stable complex with CDK2 enzyme (RMSD = 1.24 ?) in a 100 ns MD simulation. In addition, the MM-PBSA calculations ascribed the lowest binding free energy to the 7d–CDK2 complex (?323.69 ± 15.17 kJ/mol). This could be attributed to an incorporation of the 5-OCH3 group that was engaged in an extra hydrogen bonding with key THR14 amino acid residue. Finally, these results suggested hybrid 7d as a good candidate for further optimization as promising breast cancer antitumor agent and CDK2 inhibitor.
- Eldehna, Wagdy M.,El Hassab, Mahmoud A.,Abo-Ashour, Mahmoud F.,Al-Warhi, Tarfah,Elaasser, Mahmoud M.,Safwat, Nesreen A.,Suliman, Howayda,Ahmed, Marwa F.,Al-Rashood, Sara T.,Abdel-Aziz, Hatem A.,El-Haggar, Radwan
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- Simple and efficient microwave assisted N-alkylation of isatin
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We present herein the results of microwave promoted N-alkylations of isatin (1) with different alkyl, benzyl and functionalized alkyl halides. Reactions were carried out under different conditions, always employing methodologies compatible with MW assisted chemistry. Generation of isatin anion employing diverse bases and solvents or using the preformed isatin sodium salt was tested. The best results were achieved using K2CO3 or Cs 2CO3 and a few drops of N,N-dimethylformamide or N-methyl-2-pyrrolidinone. These reactions present noteworthy advantages over those carried out employing conventional heating.
- Shmidt, Maria Sol,Reverdito, Ana Maria,Kremenchuzky, Lautaro,Perillo, Isabel Amalia,Blanco, Maria Mercedes
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- Synthesis, spectroscopic characterization and antimicrobial potential of certain new isatin-indole molecular hybrids
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Molecular hybridization has a wide application in medicinal chemistry to obtain new biologically active compounds. New isatin-indole molecular hybrids 5a-n have been synthesized and characterized by various spectroscopic tools. The in vitro antimicrobial potential of the prepared compounds 5a-n was assessed using diameter of the inhibition zone (DIZ) and minimum inhibitory concentration (MIC) assays against a panel of Gram-negative bacteria, Gram-positive bacteria and fungi. Most of the synthesized compounds 5a-n showed weak activities against Gram-negative bacteria while compounds 5b and 5c exhibited good activities against Gram-positive bacteria. On the other hand, compound 5j emerged as the most active compound towards Candida albicans (C. albicans), with an MIC value of 3.9 μg/mL, and compound 5g as the most active congener towards Asperagillus Niger (A. Niger), with an MIC value of 15.6 μg/mL. Moreover, compound 5h manifested the best anti-P. notatum effect, with an MIC value of 7.8 μg/mL, making it equipotent with compound 5g.
- Al-Wabli, Reem I.,Zakaria, Azza S.,Attia, Mohamed I.
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- An efficient synthesis of new spiro[indolo-3(1H),2′(3′H)-oxadiazolyl] and 1-(triazol-4-ylmethyl)isatin derivatives
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The synthesis and the characterization of new isatin derivatives obtained by 1,3-dipolar cycloaddition reactions on allylisatin and propargylisatin are described. The products thus regiospecifically obtained in good yields bear oxadiazolyles or trizolyles
- Bouhfid, Rachid,Joly, Nicolas,Massoui, Mohamed,Cecchelli, Romeo,Lequart, Vincent,Martin, Patrick,Essassi, El Mokhtar
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- Novel mono- and bis(spiro-2-amino-4 H -pyrans): Alum-catalyzed reaction of 4-hydroxycoumarin and malononitrile with isatins, quinones, or ninhydrin
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Some new mono- and bis(spiro-2-amino-4H-pyrans) are synthesized by the multicomponent condensation reaction of 4-hydroxycoumarin and malononitrile with isatins, ninhydrin, 9,10-phenanthrenequinone, or acenaphthenequinone. Alum was found to be a suitable and efficient catalyst for this condensation. Georg Thieme Verlag Stuttgart - New York.
- Karimi, Ali Reza,Sedaghatpour, Fahime
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- Iridium-Catalyzed Enantioselective and Diastereoselective Allylation of Dioxindoles: A One-Step Synthesis of 3-Allyl-3-hydroxyoxindoles
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An iridium-catalyzed asymmetric allylation of dioxindoles, 3-hydroxyoxindoles, regulated by prosthetic groups has been accomplished under mild conditions. The methodology is applicable to a diverse array of 3-hydroxyoxindole and cinnamyl acetate substrates. A range of 3-allyl-3-hydroxyoxindoles containing vicinal tetrasubstituted and trisubstituted stereocenters can be efficiently synthesized in one-step with excellent enantioselectivity (up to >99% enaniomeric excess (ee)) and good diastereoselectivity (up to 11:1 diastereomeric ratio (dr)).
- He, Rui,Wu, Shanchao,Tang, Haoming,Huo, Xiaohong,Sun, Zhenliang,Zhang, Wanbin
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- Synthesis of novel class of n-alkyl-isatin-3-iminobenzoic acid derivatives and their biological activity in zebrafish embryos and human cancer cell lines
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Isatin (1H-indole-2,3-dione) and many of its derivatives are reported to have pharmacological properties. In this study, we report the synthesis and biological activity of a new class of N-alkyl-isatin-3-iminoben-zoic acid derivatives prepared via the condensation of N-alkyl isatin with 4-aminobenzoic acid by conventional, microwave, and ultrasonic methods. Microwave irradiation yielded the products in a shorter reaction time with higher yields and purities. The compounds were screened in zebrafish embryos, and also in three human cancer cell lines (MCF7, HepG2, and Jurkat) and one normal human cell line i.e., human foreskin cell line (HFF-1). Two compounds (3c, 3f) were found to be highly effective against hematopoiesis in live zebrafish embryo at 10μM concentration. The developmental stage-dependent treatment indicated that these compounds interfered with the differentiation of hemangioblasts to hematopoietic cells in zebrafish embryos. The comparative screening of semaxanib (SU5416) (a known isatin derivatives), to compounds synthesized in this study, revealed the contrasting effects of these two classes of isatin derivatives on zebrafish hematopoiesis. Most of the N-alkyl-isatin-3-iminobenzoic acid derivatives were toxic on cancer and non-cancer tested human cells lines, however, the compounds 3c and 3f specifically affected the cell viability of Jurkat cells (human hematological cell line) with least IC50 values of 16.5 and 7.8μM. The structure–activity relationship (SAR) analysis indicated that the substitution pattern of the isatin at the 5-position was vital for activity. The in vivo and in vitro biological activities of these compounds suggested their potential use as pharmaceutical compounds for human leukemia treatment.
- Farooq, Muhammad,Al Marhoon, Zainab Mohammed,Taha, Nael Abu,Baabbad, Almohannad Abdulrahman,Al-Wadaan, Mohammed Ahmed,El-Faham, Ayman
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- Discovery and SAR of muscarinic receptor subtype 1 (M1) allosteric activators from a molecular libraries high throughput screen. Part 1: 2,5-Dibenzyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-ones as positive allosteric modulators
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Results from a 2012 high-throughput screen of the NIH Molecular Libraries Small Molecule Repository (MLSMR) against the human muscarinic receptor subtype 1 (M1) for positive allosteric modulators is reported. A content-rich screen utilizing an intracellular calcium mobilization triple-addition protocol allowed for assessment of all three modes of pharmacology at M1, including agonist, positive allosteric modulator, and antagonist activities in a single screening platform. We disclose a dibenzyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-one hit (DBPQ, CID 915409) and examine N-benzyl pharmacophore/SAR relationships versus previously reported quinolin-3(5H)-ones and isatins, including ML137. SAR and consideration of recently reported crystal structures, homology modeling, and structure-function relationships using point mutations suggests a shared binding mode orientation at the putative common allosteric binding site directed by the pendant N-benzyl substructure.
- Han, Changho,Chatterjee, Arindam,Noetzel, Meredith J.,Panarese, Joseph D.,Smith, Emery,Chase, Peter,Hodder, Peter,Niswender, Colleen,Jeffrey Conn,Lindsley, Craig W.,Stauffer, Shaun R.
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- An efficient one pot regioselective synthesis of a 3,3′-spiro-phosphonylpyrazole-oxindole framework via base mediated [1,3]-dipolar cycloaddition reaction of the Bestmann - Ohira reagent with methyleneindolinones
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A one pot, highly regioselective synthesis of racemic 3,3′-spiro-phosphonylpyrazole-oxindole by 1,3-dipolar cycloaddition of an in situ generated anion of dialkyl 1-diazomethylphosphonate from the Bestmann-Ohira reagent (BOR) & methyleneindolinones has be
- Shelke, Anil M.,Suryavanshi, Gurunath
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- Tumor-associated carbonic anhydrase isoform IX and XII inhibitory properties of certain isatin-bearing sulfonamides endowed with in vitro antitumor activity towards colon cancer
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Three series of indolinone-based sulfonamides (3a–f, 6a–f and 9a–f) were in vitro evaluated as inhibitors of the tumor-associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII, using a stopped-flow CO2 hydrase assay. All the investigated sulfonamides displayed single- or double-digit nanomolar inhibitory activities towards both hCA IX (KIs: 6.2–64.8 nM) and XII (KIs: 7.1–55.6 nM) isoforms. All sulfonamides (3a–f, 6a–f and 9a–f) were in vitro examined for their potential anticancer activity against colorectal cancer HCT-116 and breast cancer MCF-7 cell lines. Sulfonamide 9e was found to be the most potent counterpart against HCT-116 (IC50 = 3.67 ± 0.33 μM). Sulfonamide 9e displayed good selectivity profile for inhibition of the tumor-associated isoforms (CAs IX & XII) over the off-target cytosolic CAs I and II. 9e was screened for cell cycle disturbance and apoptosis induction in HCT-116 cells. It was found to persuade cell cycle arrest at G2-M stage as well as alter the Sub-G1 phase. Also, 9e induced the intrinsic apoptotic mitochondrial pathway in HCT-116 cells via down-regulation of the anti-apoptotic protein Bcl-2 level with concurrent boosting the pro-apoptotic Bax, caspase-9, caspase-3, cytochrome C and p53 levels.
- Eldehna, Wagdy M.,Nocentini, Alessio,Al-Rashood, Sara T.,Hassan, Ghada S.,Alkahtani, Hamad M.,Almehizia, Abdulrahman A.,Reda, Ahmed M.,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
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- Asymmetric vinylogous Mukaiyama aldol reaction of isatins under bifunctional organocatalysis: Enantioselective synthesis of substituted 3-hydroxy-2-oxindoles
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A highly enantioselective organocatalytic vinylogous Mukaiyama aldol reaction of silyloxy dienes and isatins under bifunctional organocatalysis is presented. Substituted 3-hydroxy-2-oxindoles are synthesised in good yields and enantioselectivities. These
- Laina-Martín, Víctor,Humbrías-Martín, Jorge,Fernández-Salas, José A.,Alemán, José
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- Novel 4/3-((4-oxo-5-(2-oxoindolin-3-ylidene)thiazolidin-2-ylidene)amino) benzenesulfonamides: Synthesis, carbonic anhydrase inhibitory activity, anticancer activity and molecular modelling studies
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Herein we report the synthesis of two series of novel 4/3-((4-oxo-5-(2-oxoindolin-3-ylidene)thiazolidin-2-ylidene)amino)benzenesulfonamides (4a-m and 7a-g). All the newly prepared sulfonamides were in vitro investigated as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, II, IV and IX, using a stopped-flow CO2 hydrase assay. In particular, hCA isoforms II and IX (tumor-associated) were more susceptible to inhibition by the synthesized derivatives, with KIs in the range of 2.6–598.2 nM for hCA II, and of 16.1–321 nM for hCA IX. All compounds (4a-m and 7a-g) were evaluated for their anti-proliferative activity against breast cancer MCF-7 and colorectal cancer Caco-2 cell lines. Compound 4c was found to be the most potent derivative against MCF-7 (IC50 = 3.96 ± 0.21 μM), while 4j was the most active member against Caco-2 cells (IC50 = 5.87 ± 0.37 μM). Compound 4c induced the intrinsic apoptotic mitochondrial pathway in MCF-7 cells; evidenced by the enhanced expression of the pro-apoptotic protein Bax and the reduced expression of the anti-apoptotic protein Bcl-2, and the up-regulated active caspase-9 and caspase-3 levels.
- Eldehna, Wagdy M.,Abo-Ashour, Mahmoud F.,Nocentini, Alessio,Gratteri, Paola,Eissa, Ibrahim H.,Fares, Mohamed,Ismael, Omnia E.,Ghabbour, Hazem A.,Elaasser, Mahmoud M.,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
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- Metal hydride mediated reduction of 1,3-dimethyl-3(methylthio)oxindole
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The metal hydride mediated reduction of 4-carboethoxy-1,3-dimethyl-3-(methylthio)oxindole with lithium aluminum hydride and lithium triethylborohydride was studied. The results show that reduction of the oxindole carbonyl group is competitive with reducti
- Connolly, Terrence J.,Durst, Tony
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- A novel synthesis of spiro-2,5-dihydro-1,2-λ5- oxaphospholes using a three-component reaction
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The zwitterionic intermediate generated from dialkyl acetylenedicarboxylate and triphenylphosphine on reaction with N-substituted isatins leads to new highly functionalized spiro-2,5-dihydro-1,2-oxaphospholes. Georg Thieme Verlag Stuttgart.
- Esmaeili, Abbas Ali,Amini, Saeid,Bodaghi, Asghar
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- Synthesis of functionalized dispiro-oxindoles through azomethine ylide dimerization and mechanistic studies to explain the diastereoselectivity
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We have developed a one-pot synthesis of polycyclic fused dispiro-oxindole derivatives by the [3 + 3]-cycloaddition (dimerization) of azomethine ylide derived from condensation of isatin and proline. The dispiro-oxindole ring system is found at the core of a number of alkaloids, which possess significant biological activity and are interesting, challenging targets for chemical synthesis. We have demonstrated formation of two isomers, cis and trans with variable selectivity depending upon the substitution pattern at the N-atom of isatin moiety arising during this type of dimerization. We could also correlate these diastereoselectivities with DFT calculations. The formation and X-ray crystal structure of the cis isomer in this cycloaddition reaction is reported first time. We also gave clear insight into the mechanism of this dimerization reaction. the Partner Organisations 2014.
- Banerjee, Prabal,Pandey, Ashok Kumar
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- Rhodium(I)-Catalyzed Intermolecular Hydroacylation of α-Keto Amides and Isatins with Non-Chelating Aldehydes
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The application of the bidentate, electron-rich bisphosphine ligand, 1,3-bis(dicyclohexyl)phosphine-propane (dcpp), in rhodium(I)-catalyzed intermolecular ketone hydroacylation is herein described. Isatins and α-keto amides are shown to undergo hydroacylation with a variety of non-chelating linear and branched aliphatic aldehydes. Also reported is the synthesis of new bidentate chiral phosphine ligands, and their application in hydroacylation is discussed.
- Kou, Kevin G. M.,Longobardi, Lauren E.,Dong, Vy M.
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- Novel indolin-2-one-based sulfonamides as carbonic anhydrase inhibitors: Synthesis, in?vitro biological evaluation against carbonic anhydrases isoforms I, II, IV and VII and molecular docking studies
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Herein we present the design, synthesis, and biological evaluation of three different series of novel sulfonamides (3a-f, 6a-f and 9a-f) incorporating substituted indolin-2-one moieties (as tails) linked to benzenesulfonamide (as zinc anchoring moieties) through aminoethyl or (4-oxothiazolidin-2-ylidene)aminoethyl linkers. The synthesized sulfonamides were evaluated in?vitro for their inhibitory activity against the following human (h) carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, hCA I, II, IV and VII. All these isoforms were inhibited by the sulfonamides reported here in variable degrees. hCA I was inhibited with KIs in the range of 42–8550.9?nM, hCA II in the range of 5.9–761?nM; hCA IV in the range of 4.0–2069.5?nM, whereas hCA VII in the range of 13.2–694?nM. Molecular docking studies were carried out for some of the tested compounds within the hCA II active site, allowed us to rationalize the obtained inhibition results.
- Eldehna, Wagdy M.,Al-Ansary, Ghada H.,Bua, Silvia,Nocentini, Alessio,Gratteri, Paola,Altoukhy, Ayman,Ghabbour, Hazem,Ahmed, Hanaa Y.,Supuran, Claudiu T.
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- Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton
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An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ-hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo- and 86% to >99% enantioselectivities from a range of substituted isatins and γ-hydroxy enones. (Figure presented.).
- Shikari, Amit,Mandal, Koushik,Chopra, Deepak,Pan, Subhas Chandra
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p. 58 - 63
(2021/11/09)
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- New cell cycle checkpoint pathways regulators with 2-Oxo-indoline scaffold as potential anticancer agents: Design, synthesis, biological activities and in silico studies
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3-Arylidene-2-oxo-indoline derivatives are at the heart of a wide range of clinically, medicinally and biologically important compounds among the 2-oxo-indolines. A number of 3-arylidene-2-oxo-indolines have been approved for clinical application. Accordi
- Abd El-wahab, Hend A.A.,Mansour, Hany S.,Ali, Ahmed M.,El-Awady, Raafat,Aboul-Fadl, Tarek
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- Synthesis and biological evaluation of isatin derivatives containing 1,3,4-thiadiazole as potent a-glucosidase inhibitors
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A series of (Z)-3-(2-(1,3,4-thiadiazol-2-yl)hydrazono)-1-substituted indolin-2-ones derivatives (3a-3m) were designed and synthesized. All newly synthesized compounds were evaluated for their a-glucosidase inhibitory activity with resveratrol as positive control in vitro. Except for 3i and 3j, all of the compounds showed a potent inhibitory activity against a-glucosidase with IC50 values in the range of 3.12 ± 1.25 to 45.95 ± 1.26 μM and the purity of these compounds was greater than 95%. The IC50 values were being compared to the standard resveratrol (IC50 = 22.00 ± 1.15 μM) and it was found that compounds 3b, 3d-3h were found to be more active than resveratrol. Specifically, (Z)-3-(2-(1,3,4-thiadiazol-2-yl)hydrazono)-1-(4-chlorobenzyl)indolin-2-one (3d) exhibited the most potent a-glucosidase inhibitory activity with IC50 value of 3.12 ± 1.25 μM. The kinetic analysis revealed that compound (3d) is noncompetitive inhibitor. Structure activity relationship has been established for all compounds. Furthermore, the binding interactions of compound 3d with the active site of a-glucosidase were confirmed through molecular docking. This study has identified a new class of potent a-glucosidase inhibitors for further investigation.
- Zhao, Xuelian,Zhan, Xuehui,Zhang, Huilin,Wan, Yichao,Yang, Huizhong,Wang, Yutian,Chen, Yanda,Xie, Wenlin
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supporting information
(2021/11/16)
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- Organocatalytic Asymmetric Synthesis of Aza-Spirooxindoles via Michael/Friedel-Crafts Cascade Reaction of 1,3-Nitroenynes and 3-Pyrrolyloxindoles
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An asymmetric [3+3] cyclization of nitroenynes and 3-pyrrolyloxindoles has been realized with a chiral bifunctional squaramide catalyst. This Michael/Friedel-Crafts cascade strategy provides a facile and efficient access to enantioenriched polycyclic aza-spirooxindoles with 32-95% isolated yields and excellent stereocontrol under mild reaction conditions.
- Ni, Qijian,Wang, Xuyang,Zeng, Da,Wu, Qianling,Song, Xiaoxiao
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supporting information
p. 2273 - 2278
(2021/04/05)
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- Oxidative Cleavage of Indoles Mediated by Urea Hydrogen Peroxide or H2O2 in Polar Solvents
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The oxidative cleavage of indoles (Witkop oxidation) involving the use of H2O2 or urea hydrogen peroxide in combination with a polar solvent has been described. Among these solvents, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) stands out as the one affording the corresponding 2-ketoacetanilides generally in higher yields The protocol described has also enabled the oxidation of different pyrroles and furans derivatives. Furthermore, the procedure was implemented in a larger-scale and HFIP was distilled from the reaction mixture and reused (up to 4 cycles) without a significant detriment in the reaction outcome, which remarks its sustainability and applicability. (Figure presented.).
- Llopis, Natalia,Gisbert, Patricia,Baeza, Alejandro
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supporting information
p. 3245 - 3249
(2021/06/08)
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- Design, synthesis,: In silico molecular modelling studies and biological evaluation of novel indole-thiazolidinedione hybrid analogues as potential pancreatic lipase inhibitors
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Pancreatic lipase (PL) is a key enzyme responsible for the digestion of dietary triglycerides; hence its inhibition is considered as a promising target for the management and/or treatment of obesity. A new series of indole-thiazolidinedione (TZD) hybrid analogues were synthesized using a molecular hybridisation approach and evaluated for their anti-obesity effects via PL inhibition. The targeted analogues were synthesized via the condensation reaction between various substituted isatin with TZD in the presence of aqueous KOH in methanol. Amongst the synthesized analogues, 7k and 7m exhibited a potential PL inhibitory activity (IC50-7.30 and 9.51 μM, respectively). Kinetic study of these potent analogues revealed their competitive mode of enzyme inhibition. This fact was confirmed via fluorescence spectroscopy which further suggested the presence of one binding site for the synthesized analogues. Molecular docking of the synthesized analogues was performed using human PL (PDB ID: 1LPB). The obtained MolDock scores were aligned with the in vitro PL inhibitory activity (Pearson's r = 0.9108, p 0.05). Moreover, a stable conformation of the 1LPB-ligands suggested the stability of these complexes in the dynamic environment. These studies provided a basis for the potential role of the indole-TZD hybrids in PL inhibition and further optimization might result in the development of new lead candidates for obesity treatment.
- George, Ginson,Auti, Prashant S.,Paul, Atish T.
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p. 1381 - 1394
(2021/02/06)
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- Bismuth(iii)-catalyzed regioselective alkylation of tetrahydroquinolines and indolines towards the synthesis of bioactive core-biaryl oxindoles and CYP19 inhibitors
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Bismuth(iii)-catalyzed regioselective functionalization at the C-6 position of tetrahydroquinolines and the C-5 position of indolines has been demonstrated. For the first time, one pot symmetrical and unsymmetrical arylation of isatins with tetrahydroquinolines was accomplished giving a completely new product skeleton in good to excellent yields. Most importantly, this protocol leads to the formation of a highly strained quaternary carbon stereogenic center, which is a challenging task. Benzhydryl and 1-phenylethyl trichloroacetimidates have been used as the alkylating partners to functionalize the C-6 and C-5 positions of tetrahydroquinolines and indolines, respectively. The scope of the developed methodology has been extended for the synthesis of the bioactive CYP19-inhibitor and its analogue.
- Prusty, Namrata,Kinthada, Lakshmana K.,Meena, Rohit,Chebolu, Rajesh,Ravikumar, Ponneri Chandrababu
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p. 891 - 905
(2021/02/09)
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- Applications of Ytterbium(II) Reagent as Grignard Reagent and Single-Electron Transfer Reagent in the Synthesis of 3-Substituted 2-Oxindoles
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The use of ytterbium(II) reagent as both nucleophilic reagent and single-electron transfer reagent in the reaction of isatin derivatives with ytterbium(II) reagent is reported. From a synthetic point of view, a general, efficient, and experimentally simple one-pot method for the preparation of 3-substituted 2-oxindoles was developed.
- Wang, Pengkai,Cao, Xuyan,Zhang, Songlin
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supporting information
p. 3836 - 3846
(2021/07/02)
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- Microwave-assisted synthesis and antimicrobial activity of novel spiro 1,3,4-thiadiazolines from isatin derivatives
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This work describes the synthesis of spiro 1,3,4-thiadiazolines from isatin-β-thiosemicarbazone acetylation, using microwave irradiation as a source of heating the reaction medium. N-substituted isatin derivatives were used as substrates to obtain thiosemicarbazones by adding thiosemicarbazide to the isatin ketone carbonyl. The final synthetic step was the reaction of thiosemicarbazones with acetic anhydride under microwave irradiation to get the spiro compounds. Reaction times ranged from 6 to 18 minutes resulting in yields of up to 90%. Biological assays have shown promising antibacterial and antifungal activity, especially spiro thiadiazolines derived from allylated isatins. All the proposed molecules proved to be potential drug candidates based on the results of the in silico investigation, with satisfactory drug-likeness and drug-score, respecting Lipinski's rule. The use of the microwave reactor was efficient for the synthesis of thiosemicarbazones and spiro compounds, resulting in a significant reduction in reaction times with conventional heating. Taking into account the threat of antimicrobial resistance, this work presents a series of bioactive molecules that are easily obtained via microwave reaction.
- da Costa, Daniel Pereira,de Castro, Aleff Cruz,da Silva, Girlyanderson Araújo,Lima-Junior, Claudio Gabriel,de Andrade Júnior, Francisco Patricio,de Oliveira Lima, Edeltrudes,Vaz, Boniek Gontijo,da Silva, Lidya Cardoso
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p. 766 - 776
(2020/12/31)
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- Novel quinolone-based potent and selective HDAC6 inhibitors: Synthesis, molecular modeling studies and biological investigation
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In this work we describe the synthesis of potent and selective quinolone-based histone deacetylase 6 (HDAC6) inhibitors. The quinolone moiety has been exploited as an innovative bioactive cap-group for HDAC6 inhibition; its synthesis was achieved by applying a multicomponent reaction. The optimization of potency and selectivity of these products was performed by employing computational studies which led to the discovery of the diethylaminomethyl derivatives 7g and 7k as the most promising hit molecules. These compounds were investigated in cellular studies to evaluate their anticancer effect against colon (HCT-116) and histiocytic lymphoma (U9347) cancer cells, showing good to excellent potency, leading to tumor cell death by apoptosis induction. The small molecules 7a, 7g and 7k were able to strongly inhibit the cytoplasmic and slightly the nuclear HDAC enzymes, increasing the acetylation of tubulin and of the lysine 9 and 14 of histone 3, respectively. Compound 7g was also able to increase Hsp90 acetylation levels in HCT-116 cells, thus further supporting its HDAC6 inhibitory profile. Cytotoxicity and mutagenicity assays of these molecules showed a safe profile; moreover, the HPLC analysis of compound 7k revealed good solubility and stability profile.
- Relitti, Nicola,Saraswati, A. Prasanth,Chemi, Giulia,Brindisi, Margherita,Brogi, Simone,Herp, Daniel,Schmidtkunz, Karin,Saccoccia, Fulvio,Ruberti, Giovina,Ulivieri, Cristina,Vanni, Francesca,Sarno, Federica,Altucci, Lucia,Lamponi, Stefania,Jung, Manfred,Gemma, Sandra,Butini, Stefania,Campiani, Giuseppe
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- Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones
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The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.
- Wang, Rong-Hui,Li, Ya-Ling,He, Hong-Jiao,Xiao, You-Cai,Chen, Fen-Er
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supporting information
p. 4302 - 4306
(2021/02/16)
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- Dynamic Kinetic Asymmetric Transformation of Racemic Diastereomers: Diastereo- and Enantioconvergent Michael–Henry Reactions to Afford Spirooxindoles Bearing Furan-Fused Rings
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Dynamic kinetic asymmetric transformation (DYKAT) reactions of racemic diastereomer mixtures that afford the products as essentially single diastereomers with high enantioselectivities are described. We demonstrated the DYKAT in the diastereo- and enantio
- Sohail, Muhammad,Tanaka, Fujie
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supporting information
p. 21256 - 21260
(2021/08/23)
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- Copper-Catalyzed Asymmetric Propargylic Alkylation with Oxindoles: Diastereo- A nd Enantioselective Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters
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A copper-catalyzed asymmetric propargylic alkylation of propargylic acetates with 3-substituted oxindoles for the stereoselective construction of vicinal tertiary and all-carbon quaternary stereocenters in a 3,3-disubstituted oxindole skeleton has been realized. The reaction proceeded smoothly under the catalysis of Cu(MeCN)4PF6combined with a chiral tridentate ferrocenyl P,N,N ligand, leading to a broad range of optically active 3,3-disubstituted oxindoles in high yields and with excellent diastereo- A nd enantioselectivities.
- Xia, Jin-Tao,Hu, Xiang-Ping
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supporting information
p. 1102 - 1107
(2020/02/15)
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- Chiral naphthyl-C2-indole as scaffold for phosphine organocatalysis: Application in asymmetric formal [4 + 2] cycloaddition reactions
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The applications of a newly designed chiral naphthyl-C2-indole bifunctional phosphine organocatalyst in stereoselective formal [4 + 2] cycloaddition reactions were reported. The chiral naphthyl-C2-indole skeleton was introduced to bifunctional phosphine o
- He, Tingting,Peng, Lei,Li, Shan,Hu, Fangli,Xie, Chuandong,Huang, Shengli,Jia, Shiqi,Qin, Wenling,Yan, Hailong
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supporting information
p. 6966 - 6971
(2020/09/15)
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- Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides
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Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.
- Schilling, Waldemar,Zhang, Yu,Riemer, Daniel,Das, Shoubhik
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supporting information
p. 390 - 395
(2019/12/15)
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- Palladium-Catalyzed Allylation of Cyclopropyl Acetylenes with Oxindoles to Construct 1,3-Dienes
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A novel palladium-catalyzed allylic alkylation of oxindoles with cyclopropyl acetylenes has been developed. Various 1,3-diene oxindole framework bearing a quaternary stereocenter at the C3 position were synthesized straightforwardly in good to excellent yields with high regio-, and stereoselectivities. The reaction exhibited high atom economy and good functional group tolerance.
- Lu, Chuan-Jun,Yu, Xin,Chen, Yu-Ting,Song, Qing-Bao,Yang, Zhen-Ping,Wang, Hong
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p. 680 - 688
(2020/02/11)
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- Synthesis and selective inhibitory effects of some 2-oxindole benzenesulfonamide conjugates on human carbonic anhydrase isoforms CA I, CA II, CA IX and CAXII
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Three series of 2-oxindole benzenesulfonamide conjugates with different linkers were prepared by the condensation reaction of isatin derivatives 1a-e with different benzenesulfonamides. They were screened for their ability to inhibit human (h) carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, hCA II, hCA IX and hCA XII. Many compounds revealed promising activity and selectivity toward CAI, CAII and CAIX compared to acetazolamide (AAZ) especially compounds 2b (KI = 97.6, 8.0 nM against hCA I, hCA II, respectively) and 3a (KI = 90.2, 6.5 and 21.4 nM against hCA I, hCA II and hCA IX, respectively) relative to AAZ (KI = 250, 12 and 25 nM). Additionally, compound 4a revealed the highest activity against hCA II and hCA IX with KI of 3.0 and 13.9 nM, respectively. Docking of 2b, 3a and 4a into the active site of CA I, II, IX and XII revealed binding mode comparable to AAZ confirming the inhibition results.
- George, Riham F.,Said, Mona F.,Bua, Silvia,Supuran, Claudiu T.
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- Acylation of oxindoles using methyl/phenyl estersviathe mixed Claisen condensation - an access to 3-alkylideneoxindoles
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Predominantly, aggressive acid chlorides and stoichiometric coupling reagents are employed in the acylating process for synthesizing carbonyl tethered heterocycles. Herein, we report simple acyl sources,viz. methyl and phenyl esters, which acylate oxindolesviathe mixed Claisen condensation. This straightforward protocol is mediated by LiHMDS and KOtBu and successfully applied to a wide range of substrates. It is a noteworthy transformation that skips the stepwise generation of enolates and acylation, and the reaction is performed at a moderate temperature with no side reactions. This protocol produces the first examples ofortho-substituents in an aryl ring flanked with electron-donating and electron-withdrawing substrates. Interestingly, robust organometallic ferrocenyl methyl ester cleaved under these conditions with ease. Furthermore, biologically important Tenidap's analog was synthesized by this protocol.
- Gandhi, Thirumanavelan,Nagaraja, C. M.,Panyam, Pradeep Kumar Reddy,Rajeshwaran, Purushothaman,Sreedharan, Ramdas,Yadav, Saurabh
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supporting information
p. 3843 - 3847
(2020/06/03)
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- The Importance of 1,5-Oxygen???Chalcogen Interactions in Enantioselective Isochalcogenourea Catalysis
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The importance of 1,5-O???chalcogen (Ch) interactions in isochalcogenourea catalysis (Ch=O, S, Se) is investigated. Conformational analyses of N-acyl isochalcogenouronium species and comparison with kinetic data demonstrate the significance of 1,5-O???Ch interactions in enantioselective catalysis. Importantly, the selenium analogue demonstrates enhanced rate and selectivity profiles across a range of reaction processes including nitronate conjugate addition and formal [4+2] cycloadditions. A gram-scale synthesis of the most active selenium analogue was developed using a previously unreported seleno-Hugerschoff reaction, allowing the challenging kinetic resolutions of tertiary alcohols to be performed at 500 ppm catalyst loading. Density functional theory (DFT) and natural bond orbital (NBO) calculations support the role of orbital delocalization (occurring by intramolecular chalcogen bonding) in determining the conformation, equilibrium population, and reactivity of N-acylated intermediates.
- Cockroft, Scott L.,Elmi, Alex,Frost, Aileen B.,Ling, Kenneth B.,McLaughlin, Calum,Morris, Rylie K.,Pascoe, Dominic J.,Slawin, Alexandra M. Z.,Smith, Andrew D.,Smith, Terry K.,Willoughby, Patrick H.,Woods, Andrew M.,Young, Claire M.,de la Houpliere, Alix
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supporting information
p. 3705 - 3710
(2020/02/11)
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- The selective condensation of pyrazolones to isatins in aqueous medium
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The selective condensation of pyrazolones with isatins using water as the reaction medium is presented. This strategy provides an environmentally benign synthetic route to synthesize various potentially bioactive pyrazolone substituted oxindoles.
- Zhang, Yong,Nie, Long-Jun,Luo, Liang,Mao, Jia-Xin,Liu, Jin-Xiang,Xu, Guo-Hai,Chen, Deliang,Luo, Hai-Qing
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supporting information
(2020/01/08)
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- B(C6F5)3-Catalyzed Highly Chemoselective Reduction of Isatins: Synthesis of Indolin-3-ones and Indolines
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A chemo- and site-selective reduction reaction of isatin derivatives using catalyst B(C6F5)3 and hydrosilanes is described. This transformation is operationally simple, proceeds under mild conditions, and is resistant to various functional groups. Thus, this efficient reaction using a combination of B(C6F5)3 and BnMe2SiH or B(C6F5)3 and Et2SiH2 could potentially be utilized to produce various indolin-3-ones and indolines, without the need for multistep procedures and metal catalysis conditions.
- Jeong, Hyojin,Han, Nara,Hwang, Dong Wook,Ko, Haye Min
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supporting information
p. 8150 - 8155
(2020/11/02)
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- Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction
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A one-step, three-component Petasis reaction of isatin derived 5-arylboronate-3-substituted oxindole derivatives with salicylaldehydes and secondary amines affords new enantiomerically pure structurally diverse 5-α-(3-substituted-oxindole)-benzylamine derivatives. The reaction shows good substrate and reagent scope affording the products with good to excellent yields (up to >99 % yield) and enantioselectivities (up to 99 % ee) using cheap and readily available (R)-BINOL as the organocatalyst. A diastereoselective version of the reaction was also developed where moderate yields (37 to 55 % yield), excellent enantioselectivities (up to 99 % ee) and good diastereoselectivities (up to 86 % de) were obtained for new 5-α-(3-hydroxy-oxindole)-benzylamine derivatives, having two stereocenters. The reaction is also feasible on gram-scale.
- Burke, Anthony J.,Erxleben, Andrea,Marques, Carolina S.,McArdle, Patrick
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supporting information
(2020/06/30)
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- Iodine-Catalyzed Aerobic Oxidation of Spirovinylcyclopropyl Oxindoles to Form Spiro-1,2-dioxolanes Diastereoselectively
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A novel method of iodine-catalyzed aerobic oxidation with spirovinylcyclopropyl oxindoles under mild conditions has been described. A series of spiro-1,2-dioxolanes were prepared in good to excellent yields and considerable diastereoselectivities. The new approach is operationally simple, scalable, and tolerant of various functional groups.
- Xiong, Cheng,Cheng, Kunpeng,Wang, Jiahua,Yang, Fulai,Lu, Jinrong,Zhou, Qingfa
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p. 9386 - 9395
(2020/08/14)
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- Design and synthesis of novel isatin-based derivatives targeting cell cycle checkpoint pathways as potential anticancer agents
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In recent years, cell cycle and checkpoint pathways regulation are offering new therapeutic approaches against cancer. Isatin, is a well exploited scaffold in the anticancer domain. Accordingly, the current work describes the design and synthesis of two series of (Z)-3-substituted-2-(((E/Z)-5-substituted-2-oxo-1-substituted-indolin-3-ylidene)hydrazinylidene)-thiazolidin-4-ones, 4(a-s) and (E/Z)-1-substituted-3-(((Z)-3-substituted-4-methylthiazol-2(3H)-ylidene)hydrazineylidene)-5-substituted-indolin-2-ones, 5(a-s). The structures of the synthesized molecules were confirmed by spectral and elemental methods of analyses. Pure diastereomers were further identified with 1H-1H-NOESY and confirmed with X-ray crystallography. The target compounds were tested in vitro for their cytotoxicity against three human epithelial cell lines, liver (HepG2), breast (MCF-7), and colon (HT-29) in addition to the diploid human normal cells (WI-38) compared to doxorubicin as a reference drug. Variable cytotoxic effects (IC50 3.29–100 ?μmol) were reported on the three cancer cell lines with pronounced selectivity compared to the normal one WI-38. The potency of the most active compounds, 4o, 4s, 5e, 5f, 5l, 5m and 5o (IC50 3.29–9.92 ?μmol), in both series associated with the (Z) configurations of N = thiazolidin/ene or one, however, the configuration of the N = isatin moiety seemed to be of no importance to the activity. The tested compounds were grouped for their possible mechanism of action into 4 categories. Compound 4o with no apparent effect on all genes examined. Compounds 4s and 5o affected all genes investigated and seem to have multiple cellular targets; induced the expression of p53 and caspases, and downregulated that of CDK1. Compounds 5l and 5m directly elevated the expression of initiator and effector caspases without going through p53 pathway. Finally, compounds 5e and 5f elevated the expression of p53 and inhibited CDK1. Compounds 4s, 5e, 5f, 5l, 5m, and 5o caused a significant elevation in the activity of cleaved caspase 3 as well. Docking studies on CDK1 revealed that the active molecules bind to the tested enzyme by the same manner of the co-crystallized ligands and the isatin-thiazoldinone/ene scaffold is essential for binding of these molecules.
- Yousef, Mohamed A.,Ali, Ahmed M.,El-Sayed, Wael M.,Quayed, Wesam S.,Farag, Hassan H.A.,Aboul-Fadl, Tarek
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- Transformations of N-arylpropiolamides to indoline-2,3-diones and acids via C≡C triple bond oxidative cleavage and C(sp2)–H functionalization
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A new palladium-catalyzed oxidative conversion of N-arylpropiolamides and H2O to various indoline-2,3-diones and acids through the C≡C triple bond cleavage and C(sp2)–H functionalization is described, which is promoted by a cooperative action of catalytic CuBr2, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and O2. The method provides a practical tool for transformations of alkynes by means of a C–H functionalization strategy, which enables the formation of one C–C bond and multiple C–O bonds in a single reaction with high substrates compatibility and excellent functional group tolerance.
- Zhou, Ming-Bo,Li, Yang,Ouyang, Xuan-Hui,Li, Jin-Heng
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p. 222 - 227
(2019/11/13)
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- Shielding Effect of Micelle for Highly Effective and Selective Monofluorination of Indoles in Water
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Highly selective direct monofluorination of indoles and arenes was developed through an approach that allows site-specific solubility of substrate and fluorine source in the micelle. This approach was highly selective for a broad range of substrates with excellent functional group tolerance. Differences in binding constant and solubility of indoles and arenes in the micelle allowed the fine-tuning of selectivity. Control experiments suggested a radical pathway and provided insight into the role of micelles of the environmentally benign amphiphile PS-750-M. Dynamic light scattering experiments strongly indicated the site-specific solubility of the substrate and fluorine source. The methodology was successfully adapted to gram scale, and the E-factor established from a recycle study indicated that the process is environmentally responsible and sustainable.
- Bora, Pranjal P.,Bihani, Manisha,Plummer, Scott,Gallou, Fabrice,Handa, Sachin
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p. 3037 - 3042
(2019/04/01)
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- NHC-Catalyzed Aldol-Like Reactions of Allenoates with Isatins: Regiospecific Syntheses of γ-Functionalized Allenoates
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An N-heterocyclic carbene (NHC) catalyzed γ-specific aldol-like reaction between allenoates and isatins has been achieved under mild conditions, giving trisubstituted allene derivatives bearing isatin moiety in moderate to good yields with high diastereoselectivity and excellent atom efficiency. The DFT computations indicated that the formation of the γ-adduct was more energetically favorable than that of the α-adduct. The result reported herein opens a new route for NHC-promoted allenoate-involved reaction.
- Li, Sha,Tang, Ziwei,Wang, Yang,Wang, Dan,Wang, Zhanlin,Yu, Chenxia,Li, Tuanjie,Wei, Donghui,Yao, Changsheng
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supporting information
p. 1306 - 1310
(2019/02/26)
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- Novel Multitarget Directed Triazinoindole Derivatives as Anti-Alzheimer Agents
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The multifaceted nature of Alzheimer's disease (AD) demands treatment with multitarget-directed ligands (MTDLs) to confront the key pathological aberrations. A novel series of triazinoindole derivatives were designed and synthesized. In vitro studies revealed that all the compounds showed moderate to good anticholinesterase activity; the most active compound 23e showed an IC50 value of 0.56 ± 0.02 μM for AChE and an IC50 value of 1.17 ± 0.09 μM for BuChE. These derivatives are also endowed with potent antioxidant activity. To understand the plausible binding mode of the compound 23e, molecular docking studies and molecular dynamics simulation studies were performed, and the results indicated significant interactions of 23e within the active sites of AChE as well as BuChE. Compound 23e successfully diminished H2O2-induced oxidative stress in SH-SY5Y cells and displayed excellent neuroprotective activity against H2O2 as well as Aβ-induced toxicity in SH-SY5Y cells in a concentration dependent manner. Furthermore, it did not show any significant toxicity in neuronal SH-SY5Y cells in the cytotoxicity assay. Compound 23e did not show any acute toxicity in rats at doses up to 2000 mg/kg, and it significantly reversed scopolamine-induced memory deficit in mice model. Additionally, compound 23e showed notable in silico ADMET properties. Taken collectively, these findings project compound 23e as a potential balanced MTDL in the evolution process of novel anti-AD drugs.
- Patel, Dushyant V.,Patel, Nirav R.,Kanhed, Ashish M.,Patel, Sagar P.,Sinha, Anshuman,Kansara, Deep D.,Mecwan, Annie R.,Patel, Sarvangee B.,Upadhyay, Pragnesh N.,Patel, Kishan B.,Shah, Dharti B.,Prajapati, Navnit K.,Murumkar, Prashant R.,Patel, Kirti V.,Yadav, Mange Ram
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p. 3635 - 3661
(2019/08/20)
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- "on Water" Direct Organocatalytic Cyanoarylmethylation of Isatins for the Diastereoselective Synthesis of 3-Hydroxy-3-cyanomethyl Oxindoles
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An "on water" organocatalytic cyanoarylmethylation of aryl acetonitrile to isatins is developed, giving products in high yields and up to excellent diastereoselectivities. A remarkable enhancement of reaction rates and diastereoselectivities by water was observed under mild conditions. Moreover, this approach provides a highly efficient and environmentally benign access to thermodynamic 3-hydroxy-3-cyanomethyl oxindoles.
- Zhang, Yong,Luo, Liang,Ge, Jin,Yan, Su-Qiong,Peng, Yan-Xin,Liu, Ya-Ru,Liu, Jin-Xiang,Liu, Chong,Ma, Tianqiong,Luo, Hai-Qing
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p. 4000 - 4008
(2019/03/29)
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- Enantioselective Rhodium-Catalyzed Addition of Arylboroxines to N-Unprotected Ketimines: Efficient Synthesis of Cipargamin
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Highly enantioselective rhodium-catalyzed addition of arylboroxines to N-unprotected ketimines is realized for the first time by employing chiral BIBOP-type ligands with a Rh loading as low as 1 mol %. A range of chiral α-trifluoromethyl-α,α-diaryl α-tertiary amines or 3-amino-3-aryloxindoles were formed with excellent ee values and yields by employing either WingPhos or PFBO-BIBOP as the ligand. The method has enabled an efficient enantioselective synthesis of cipargamin.
- Zhu, Jinbin,Huang, Linwei,Dong, Wei,Li, Naikai,Yu, Xingxin,Deng, Wei-Ping,Tang, Wenjun
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supporting information
p. 16119 - 16123
(2019/11/03)
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- Transition-metal-free addition reaction for the synthesis of 3-(aminobenzylidene/aminoalkylidene)indolin-2-ones and its synthetic applications
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A novel and efficient transition-metal-free approach for the exclusive synthesis of Z-3-(aminobenzylidene/aminoalkylidene)indolin-2-ones in high yield from 2-oxindole and aryl/alkyl nitrile in the presence of LiOtBu and 2,2′-bipyridine system is described. In addition, we disclosed a new approach towards the metal-free fluorination using selectfluor and the C=C bond cleavage using CuI and environmentally benign O2.
- Bisht, Girish Singh,Gnanaprakasam, Boopathy
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supporting information
p. 13516 - 13527
(2019/10/19)
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- 3-Hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one as a versatile intermediate for retro-Henry and Friedel-Crafts alkylation reactions in aqueous medium
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The first example of a retro-Henry type reaction is reported using 3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-ones which are prepared via catalyst-free Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin. These compounds were used
- Nagaraju, Sakkani,Sathish, Kota,Paplal, Banoth,Satyanarayana, Neeli,Kashinath, Dhurke
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p. 14045 - 14050
(2019/09/18)
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- Reactivity of spiroanthraceneoxazolidines with cyclopropanes: An approach to the oxindole alkaloid scaffold
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The reaction of N-methylspiro[anthracene-oxazolidine] with spiro[cyclopropane-3,3′-indolin]-2-ones in the presence of MgI2 formed the corresponding spiro[pyrrolidine-3,3′-indolin]-2-ones in 42–65% yields. The use of N-benzylspiro[anthracene-oxazolidine] in this reaction led to the formation of a mixture of the corresponding N-methyl- and N-benzylpyrrolidines.
- Buev, Evgeny M.,Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Y.
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supporting information
p. 3409 - 3412
(2018/08/20)
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- Indolone derivative containing 1,3,4-thiadiazole as well as preparation method and application
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The invention provides an indolone derivative containing 1,3,4-thiadiazole shown as a formula (I), a novel N-substituted-3-(1,3,4-thiadiazole-2-yl)hydrazonoindole-2-ketone compound and a preparation method thereof. In the formula (I), a substituent group R is H, CH3, CH2CH3, CH2CH2CH3, CH3O, Cl, Br, F, NO2, CN, F3C or SO3OH group. The N-substituted-3-(1,3,4-thiadiazole-2-yl)hydrazonoindole-2-ketone compound provided by the invention has certain inhibition activity on alpha-glucosidase; a synthesis method is simple and materials are easy to obtain. The compound can be used for producing a drugfor inhibiting the alpha-glucosidase. The formula (I) is shown in the description.
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Paragraph 0015-0016
(2018/10/11)
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- Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles
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Rationally designed fluorene-based mono- and bimetallic Pd-PEPPSI complexes were synthesized and demonstrated to be effective for the one-pot sequential α-arylation/alkylation of oxindoles. This streamlined approach offers efficient access to functionalized 3,3-disubstituted oxindoles in excellent yields (up to 89%) under mild reaction conditions.
- Reddy Panyam, Pradeep Kumar,Ugale, Bharat,Gandhi, Thirumanavelan
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p. 7622 - 7632
(2018/06/22)
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- Cinchona-alkaloid-catalyzed enantioselective hydroxymethylation of 3-fluorooxindoles with paraformaldehyde
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Cinchona-alkaloid-catalyzed hydroxymethylation of 3-fluorooxindoles using paraformaldehyde as the C1 unit was achieved. A wide range of 3-fluorooxindoles was successfully reacted to give the corresponding 3-fluoro-3-hydroxymethyloxindoles with high efficiency and moderate to good enantioselectivity.
- Zhao, Jian-bo,Ren, Xinfeng,Zheng, Bu-quan,Ji, Jian,Qiu, Zi-bin,Li, Ya
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supporting information
p. 44 - 51
(2018/10/02)
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- Nickel(II)-Catalyzed Asymmetric Propargyl [2,3] Wittig Rearrangement of Oxindole Derivatives: A Chiral Amplification Effect
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A highly enantioselective [2,3] Wittig rearrangement of oxindole derivatives was realized by using a chiral N,N′-dioxide/NiII complex as the catalyst under mild reaction conditions. A strong chiral amplification effect was observed, and allowed access to chiral 3-hydroxy 3-substituted oxindoles bearing allenyl groups in high yields and enantioselectivities (up to 92 % ee) by using a ligand with only 15 % ee. A reasonable explanation was given based on the experimental investigations and X-ray crystal structures of enantiomerically pure and racemic catalysts. Moreover, the first catalytic kinetic resolution of racemic oxindole derivatives by a [2,3] Wittig rearrangement was realized with high efficiency and stereoselectivity.
- Xu, Xi,Zhang, Jianlin,Dong, Shunxi,Lin, Lili,Lin, Xiaobin,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 8734 - 8738
(2018/07/14)
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- Palladium-Catalyzed Oxidation of Indoles to Isatins by tert -Butyl Hydroperoxide
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The combination of a Pd catalyst and tert -butyl hydroeroxide (TBHP) is a powerful catalytic system for many types of oxidative transformations. Here, we report that a Pd/TBHP system facilitates the oxidation of indoles with a range of functionalities to give the corresponding isatin derivatives in good yields.
- Luo, Junfei,Gao, Shanshan,Ma, Yaorui,Ge, Guoping
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supporting information
p. 969 - 973
(2018/02/09)
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- Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates
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The previously unexplored Grignard addition to oxindoles provides a regiospecific approach to 2- and 2,3-disubstituted indole derivatives in high yields via a one-pot aromatization driven dehydration pathway. This method allows a convenient preparation of diallyl indoles that are used as ring-closing metathesis (RCM) precursors for the orthogonal synthesis of pyrido[1,2-a]indoles and carbazoles. The synthetic utility of this method is illustrated by the synthesis of a microtubulin inhibitor and naturally occurring carbazole alkaloids.
- Mandal, Tirtha,Chakraborti, Gargi,Karmakar, Shilpi,Dash, Jyotirmayee
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supporting information
p. 4759 - 4763
(2018/08/24)
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- Indium-mediated Palladium-catalyzed Allylic Alkylation of Isatins with Alkynes
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An unprecedented indium-mediated palladium-catalyzed allylic alkylation of isatins with alkynes is disclosed. This reaction provides a new, practical, and straightforward route to access 3-allyl-3-hydroxy-2-oxindoles in good yields with broad substrate scope and scalability, exhibiting high atom and step economy. A primary mechanistic study reveals that indium played two roles in the reaction, first as a reductant and second as a Lewis acid. Compared with previous methods, our strategy eliminated the steps for the separation and purification of the reaction intermediates, as well as pre-installing leaving groups to allylic substrates. Moreover, our reaction did not employ moisture-sensitive allylic metal species and stoichiometric oxidants. (Figure presented.).
- Wu, Zijun,Fang, Xinxin,Leng, Yuning,Yao, Hequan,Lin, Aijun
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supporting information
p. 1289 - 1295
(2018/02/21)
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- Synthesis method of indole-2,3-dione compound
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The invention discloses a synthesis method of an indole-2,3-dione compound. The method comprises the following steps that a raw material as shown in a formula I is added into a Schlenk reactor, then acatalyst bis(acetonitrile)dichloropalladium (PdCl2(CH3CN)2), an oxidizing agent silver acetate (AgOAc) and a solvent methylbenzene are added, reaction is carried out under an oxygen atmosphere at 120-150 DEG C for 8-36 hours, a TLC board is used for monitoring the reaction, and after the reaction is carried out completely, the indole-2,3-dione compound as shown in a formula II is obtained throughpost-treatment.
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Paragraph 0030; 0040-0042
(2018/12/05)
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- Method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid
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The invention discloses a method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid. The method comprises the following steps: a catalytic amount of catalyst copper iodide, indole, a derivative of the indole and peroxyacetic acid are added into a reaction vessel, wherein the indole, the derivative of the indole and the peroxyacetic acid are usedas raw materials, ethanol is used as a solvent, the reaction vessel is placed into a microwave reaction instrument, a reaction is performed at certain temperature and power, after a certain time, reduced-pressure concentration is performed, and a product is purified by column chromatography. The method provided by the invention is a method having novel raw materials, simple operation and high efficiency used for preparing a benzimidazole derivative; and compared with the prior art, the method provided by the invention has an obviously-accelerated reaction speed than that under conventional heating, mild reaction conditions, simple operation, a high yield, safety, low costs and environmental protection.
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Paragraph 0024; 0029
(2018/09/08)
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- A C=O???Isothiouronium Interaction Dictates Enantiodiscrimination in Acylative Kinetic Resolutions of Tertiary Heterocyclic Alcohols
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A combination of experimental and computational studies have identified a C=O???isothiouronium interaction as key to efficient enantiodiscrimination in the kinetic resolution of tertiary heterocyclic alcohols bearing up to three potential recognition motifs at the stereogenic tertiary carbinol center. This discrimination was exploited in the isothiourea-catalyzed acylative kinetic resolution of tertiary heterocyclic alcohols (38 examples, s factors up to >200). The reaction proceeds at low catalyst loadings (generally 1 mol %) with either isobutyric or acetic anhydride as the acylating agent under mild conditions.
- Greenhalgh, Mark D.,Smith, Samuel M.,Walden, Daniel M.,Taylor, James E.,Brice, Zamira,Robinson, Emily R. T.,Fallan, Charlene,Cordes, David B.,Slawin, Alexandra M. Z.,Richardson, H. Camille,Grove, Markas A.,Cheong, Paul Ha-Yeon,Smith, Andrew D.
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supporting information
p. 3200 - 3206
(2018/02/22)
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- Palladium-catalyzed silaborative carbocyclizations of 1,6-diynes
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An addition/cyclization reaction of 1,6-diynes was developed for the synthesis of highly substituted 1,2-dialkylidenecycloalkanes. In this work, 1,6-diynes reacted with (dimethylphenylsilyl)pinacol-borane in the presence of a palladium catalyst to afford 1,2-dialkylidenecycloalkanes bearing silyl and boryl groups with a (Z,Z)-configuration in good to excellent yields. Moreover, the corresponding products could be easily converted into other synthetically useful compounds. This protocol provides an efficient and practical method of heteroelement-element linkage addition to the unsaturated 1,6-diynes.
- Zhang, Qian,Liang, Qiu-Ju,Xu, Jian-Lin,Xu, Yun-He,Loh, Teck-Peng
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supporting information
p. 2357 - 2360
(2018/03/13)
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- Indole-2-ketone-3-spirobuprofezin or thiazolone compound and application thereof
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The invention discloses an indole-2-ketone-3-spirobuprofezin or thiazolone compound shown as a formula I or pharmaceutically acceptable salt thereof or a stereoisomer thereof and application thereof to preparation of a medicine for preventing and treating
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Paragraph 0066-0068
(2018/04/03)
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