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Microwave-Assisted Synthesis, Molecular Docking Studies and Biological Evaluation of Benzothiazole Containing Novel Indole Derivatives
The synthesis of novel indole derivatives 4a-o using a microwave assisted method via Schiff’s base and Mannich base reaction mechanism was described. Compounds 3a-c were synthesized via reaction of 2-amino benzothiazole with substituted isatin by Schiff base reaction mechanism. Also, indole derivatives 4a-o were synthesized via reaction of compounds 3a-c with substituted benzaldehydes by Mannich base reaction. The biological potentials of the newly synthesized indole derivatives were evaluated for their anthelmintic activity and in vitro anticancer activity by MTT assay. The anticancer activity results suggested that indole derivatives 4c-o have activity against MCF-7 and SKOV3 cells in comparison with doxorubicin as standard drug. Furthermore, the molecular docking studies of these novel derivatives of indole showed good agreement with the biological results when their binding pattern and affinity towards the active site of EGFR was also investigated.
Pandian, P.,Rajkamal, B.,Sultana, Shaheen
p. 2755 - 2761
(2021/10/25)

Quinoline carboxamide core moiety-based compounds inhibit P. falciparum falcipain-2: Design, synthesis and antimalarial efficacy studies
Targeting Falcipain-2 (FP2) for the development of antimalarials is a promising and established concept in antimalarial drug discovery and development. FP2, a member of papain-family cysteine protease of the malaria parasite Plasmodium falciparum holds an important role in hemoglobin degradation pathway. A new series of quinoline carboxamide-based compounds was designed, synthesized and evaluated for antimalarial activity. We integrated molecular hybridization strategy with in-silico drug design to develop FP2 inhibitors. In-vitro results of FP2 inhibition by Qs17, Qs18, Qs20 and Qs21 were found to be in low micromolar range with IC50 4.78, 7.37, 2.14 and 2.64 μM, respectively. Among the 25 synthesized compounds, four compounds showed significant antimalarial activities. These compounds also depicted morphological and food-vacuole abnormalities much better than that of E-64, an established FP2 inhibitor. Overall these aromatic substituted quinoline carboxamides can serve as promising leads for the development of novel antimalarial agents.
Singh, Anju,Kalamuddin, Md,Maqbool, Mudasir,Mohmmed, Asif,Malhotra, Pawan,Hoda, Nasimul
(2020/12/07)

Design, synthesis, and in vitro and in vivo anti-angiogenesis study of a novel vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitor based on 1,2,3-triazole scaffold
In the past five years, our team had been committed to click chemistry research, exploring the biological activity of 1,2,3-triazole by synthesizing different target inhibitors. In this study, a series of novel indole-2-one derivatives based on 1,2,3-triazole scaffolds were synthesized for the first time, and their inhibitory activity on vascular endothelial growth factor receptor-2 (VEGFR-2) was tested. Most of the compounds had shown promising activity in the VEGFR-2 kinase assay and had low toxicity to human umbilical vein endothelial cells (HUVECs). The compound 13d (IC50 = 26.38 nM) had better kinase activity inhibition ability than sunitinib (IC50 = 83.20 nM) and was less toxic to HUVECs. Moreover, it had an excellent inhibitory effect on HT-29 and MKN-45 cells. On the one hand, by tube formation assay, transwell, and Western blot analysis, compound 13d could inhibit VEGFR-2 protein phosphorylate on HUVECs, thereby inhibiting HUVECs migration and tube formation. In vivo study, the zebrafish model with VEGFR-2 labeling also verified that compound 13d had more anti-angiogenesis ability than sunitinib. On the other hand, molecular docking and molecular dynamics (MD) simulation results showed that compound 13d could stably bind to the active site of VEGFR-2. Based on the above findings, compound 13d could be considered an effective anti-angiogenesis drug and has more development value than sunitinib.
Wang, De-pu,Liu, Kai-li,Li, Xin-yang,Lu, Guo-qing,Xue, Wen-han,Qian, Xin-hua,Mohamed O, Kamara,Meng, Fan-hao
(2020/12/21)

Cs 2CO 3-Mediated Regio- And Stereoselective Sulfonylation of 1,1-Dibromo-1-alkenes with Sodium Sulfinates
A highly selective synthesis of (Z)-1-bromo-1-sulfonyl alkenes via Cs 2CO 3-promoted sulfonylation of 1,1-dibromo-1-alkenes with sodium sulfinates is described. Notably, using excess amounts of Cs 2CO 3and sodium sulfinate in such a reaction regenerated the parent aldehyde. Interestingly, the reaction of 1-(2,2-dibromovinyl)-2-nitrobenzene in the presence of sulfinates and Cs 2CO 3produced isatin. The Sonogashira cross coupling of synthesized (Z)-1-bromo-1-sulfonyl alkenes with phenylacetylene gave selectively the corresponding sulfonylalkynyl alkenes.
Shiri, Morteza,Salehi, Parvin,Mohammadpour, Zeinab,Salehi, Peyman,Notash, Behrouz
p. 1149 - 1156
(2020/10/21)

1,3-CYCLOHEXANEDIONE DERIVATIVES AND 1,3-CYCLOPENTANEDIONE DERIVATIVES AS BUFFERING MOLECULES IN NON-AQUEOUS SOLUTIONS
This invention relates to 1,3-cyclohexanedione derivatives and 1,3-cyclopentanedione derivatives that have buffering function in non-aqueous solutions and to the use thereof for tuning the conditions to control chemical events in non-aqueous solutions. One aspect of the invention is a method for buffering a non-aqueous solution, including adding a buffering molecule to the non-aqueous solution, in which the non-aqueous solution contains an organic solvent, the buffering molecule is a 1,3-cyclohexanedione derivative or a 1,3-cyclopentanedione derivative, and the buffering molecule is optionally conjugated to a solid support.
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Paragraph 0059

(2021/04/23)

Pyrrole drug molecule with sterilization and disinfection effects as well as preparation method and application of pyrrole drug molecule
The invention discloses a pyrrole drug molecule with sterilization and disinfection effects as well as a preparation method and application of the pyrrole drug molecule, and belongs to the technical field of antibacterial drug synthesis. The key point of the technical scheme is that the pyrrole drug molecule has a structure, wherein R is or R1 and R2 are halogen atoms, alkyl groups, aryl groups, heterocyclic rings and the like. The inventor finds a simple and efficient method for preparing diketoindoline by taking aniline as a raw material, and besides, finds a method capable of obtaining carbon-nitrogen double bonds and carbon-nitrogen single bonds, which has a great prospect in structural modification of compounds. The pyrrole drug molecule obtained by the invention has a good inhibition effect on staphylococcus aureus.
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Paragraph 0021-0032

(2022/01/10)

Hydrothermal Preparation, Crystal Structure, Photophysical Properties and Theoretical Calculation of a Cu(II) Complex
Abstract: A novel Cu(II) compound [CuL2]·2H2O was synthesized by hydrothermal methods, and its crystal structure was determined by single-crystal X-ray diffraction. The title compound crystallized in the monoclinic space group P21/c as an isolated monocyte structure. The strong π…π stacking and hydrogen bonding interactions produce one-dimensional (1D) chains. A series of properties of the title compound were tested by solid state photoluminescence, CIE analysis and solid-state diffuse reflectance. The results show that the compound is a blue light emitter, CIE (0.1291, 0.0783) and has an energy bandwidth of 1.65?eV. Time-dependent density functional theory (TDDFT) calculation results show that the emission of the compound can be attributed to charge transfer from metal to ligand and ligand to ligand (MLCT and LLCT). Graphic Abstract: A novel Cu (II) complex is synthesized via hydrothermal preparation, which is characteristic of an isolated structure, at the same time, it displays a narrow and intense photoluminescence emission band in the blue region and theoretical study reveals that the photoluminescence emission is originated from the metal-to-ligand and ligand-to-ligand charge transfer transition. [Figure not available: see fulltext.]
Wang, Yin-Feng,Yi, Xiu-Guang,Fang, Xiao-Niu,Guo, Jin,Lai, Fei-Ping,Xie, Shi-Kun
p. 169 - 174
(2020/05/29)

A rhodium(ii) catalysed domino synthesis of azepino fused diindoles from isatin tethered: N -sulfonyl-1,2,3-triazoles and indoles
An efficient and convenient protocol for the synthesis of a novel class of azepino fused diindoles from isatin tethered N-sulfonyl-1,2,3-triazoles and indoles has been disclosed. The reaction proceeds via denitrogenative aza-vinyl rhodium carbene formation to give a carbonyl ylide, which with indole results in 1,3-dipolar cycloaddition followed by sequential semipinacol rearrangement/ring expansion/oxidation to produce azepino fused diindoles. The reaction shows a broad substrate scope giving up to 81% yield. Furthermore, reversible catalytic hydrogenation and photophysical studies were carried out to demonstrate the application of these molecules.
Kahar, Nilesh,Jadhav, Pankaj,Reddy, R. V. Ramana,Dawande, Sudam
supporting information
p. 1207 - 1210
(2020/02/04)

Iron-catalyzed cross-dehydrogenative coupling of indolin-2-ones with active methylenes for direct carbon-carbon double bond formation
The iron-catalyzed cross-dehydrogenative coupling (CDC) of C(sp3)-H/C(sp3)-H bonds to afford olefins by 4H elimination is described. This method employs air (molecular oxygen) as an ideal oxidant, and is performed under mild, ligand-free and base-free conditions. H2O is the only byproduct. Good tolerance of functional groups and high yields have also been achieved. Preliminary mechanistic investigations suggest that the present transformation involves a radical process.
Tan, Zhi-Yu,Wu, Ke-Xin,Huang, Lu-Shan,Wu, Run-Shi,Du, Zheng-Yu,Xu, Da-Zhen
p. 332 - 335
(2020/02/13)

Iron-Catalyzed Direct Oxidative Alkylation and Hydroxylation of Indolin-2-ones with Alkyl-Substituted N-Heteroarenes
Presented herein is the first direct alkylation and hydroxylation reaction between two different C(sp3)?H bonds, indolin-2-ones and alkyl-substituted N-heteroarenes, through an oxidative cross-coupling reaction. The reaction is catalyzed by a simple iron salt under mild ligand-free and base-free conditions. The reaction is environmentally benign, employs air (molecular oxygen) as the terminal oxidant and oxygen source for the synthesis of O-containing compounds, and produces only water as the byproduct.
Feng, Yu,Han, Dong-Yang,Hu, Ren-Ming,Huang, Jie,Li, Ning,Xu, Da-Zhen
supporting information
p. 3876 - 3880
(2020/02/05)

Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides
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
supporting information
p. 390 - 395
(2019/12/15)

Iron-Catalyzed Oxidative Coupling of Indoline-2-ones with Aminobenzamides via Dual C-H Functionalization
We describe an unprecedented dual C-H functionalization of indolin-2-one via an oxidative C(sp3)-H/N-H/X-H (X = N, C, S) cross-coupling protocol, which is catalyzed by a simple iron salt under mild and ligand-free conditions and employs air (molecular oxygen) as the terminal oxidant. This method is readily applicable for the construction of tetrasubstituted carbon centers from methylenes and provides a wide variety of spiro N-heterocyclic oxindoles.
Lai, Yi-Huan,Wu, Run-Shi,Huang, Jie,Huang, Jun-Yu,Xu, Da-Zhen
supporting information
p. 3825 - 3829
(2020/05/18)

Tryptanthrin from indigo: Synthesis, excited state deactivation routes and efficient singlet oxygen sensitization
The microwave-assisted synthesis of tryptanthrin from indigo in mild oxidation conditions, and a comprehensive study of the excited state properties of this compound in a variety of solvents with different polarity and viscosity values at room and low temperatures are reported. In contrast with indigo, emission of the triplet state of tryptanthrin is observed with a very efficient singlet oxygen sensitization quantum yield, indicating that the triplet state is efficiently populated. From time-resolved fluorescence and femtosecond transient absorption data, further supported with time-dependent density functional theory (TDDFT) calculations, two species, with S1 states with locally excited (LE) of π,π* nature and a charge transfer (CT) of n,π* characteristics, originated from an initially populated Frank-Condon S2 state (π,π*), are observed. The two electronically independent species are energetically nearly degenerate and inter-conversion is predicted (and rate constants determined) to occur between LE (S1) and CT (S1) species. Due to the low value of the fluorescence quantum yield (~10?3) and high triplet state yield (?T≥?Δ), the high stability of this compound is associated to the high efficiency of the radiationless deactivation processes which involve the formation of the CT state which efficiently converts, through S1 ~~> Tn intersystem crossing, to the T1 triplet state.
Pinheiro, Daniela,Pineiro, Marta,Pina, Jo?o,Brand?o, Pedro,Galv?o, Adelino M.,Seixas de Melo, J. Sérgio
(2019/12/28)

Direct Catalytic Asymmetric Synthesis of Oxindole-Derived δ-Hydroxy-β-ketoesters by Aldol Reactions
Direct asymmetric synthesis of δ-hydroxy-β-ketoesters was accomplished via regio- and enantioselective aldol reactions of β-ketoesters with isatins catalyzed by cinchona alkaloid thiourea derivatives. The C-C bond formation of the reactions occurred only at the γ-position of the β-ketoesters. Reaction progress monitoring and product stability analyses under the conditions that included the catalyst indicated that the γ-position reaction products were formed kinetically. Various δ-hydroxy-β-ketoesters bearing 3-alkyl-3-hydroxyoxindole cores relevant to the development of bioactive molecules were synthesized.
Zhang, Dongxin,Chen, Yan,Cai, Hu,Yin, Lei,Zhong, Junchao,Man, Jingjing,Zhang, Qian-Feng,Bethi, Venkati,Tanaka, Fujie
supporting information
p. 6 - 10
(2019/11/28)

Serendipitous Formation of Semiconducting Semi-Nindigo Indigoid by the Degradation of Diindolopyrrole
We report the serendipitous discovery and synthesis of an indigoid semi-Nindigo (2) via oxidation of a diindolopyrrole (1). The reaction of 2 with BF3Et2O affords the borylated derivative (3). The electronic spectra of 2 and 3 possess intense long wave absorptions near 600 and 650 nm. Compound 3 is weakly emissive in the near-infrared. Thin-film OFETs fabricated with 1 and 2 both exhibited hole mobility of 10-5 and 10-3 cm2/(V s), respectively.
Dadvand, Afshin,Perepichka, Dmitrii F.,Yee, Nathan
p. 5073 - 5077
(2020/05/01)

Synthesis, Characterization, Properties, and Theoretical Calculation of an Inorganic–Organic Hybrid Mononuclear Copper(II) Complex Containing 3-Hydroxy-2-methyl-quinoline-4-carboxylate
Abstract: A novel copper complex [CuL(bipy)(H2O)]·H2O was synthesized by solvothermal reaction and its crystal structure was determined by single-crystal X-ray diffraction technique. (HL = 3-hydroxy-2-methylquinoline4-carboxylic acid; bipy = 2,2′-bipyrdine) The title complex (1) crystallizes in the orthorhombic system of the Pbca space group, and exists as an isolated mononuclear structure. The intermolecular hydrogen bonds and the strong π···π stacking interactions yield a three-dimensional (3-D) supramolecular network. Solid-state photoluminescence spectrum uncovers that it shows an emission in the pale blue region of the light spectrum. It has remarkable CIE (Commission Internationale de I’éclairage) chromaticity coordinates of (0.2656, 0.3162), so it may be a very promising color lighting and display converter. Time-dependent density functional theory (TDDFT) calculation reveals that this emission is caused by to the ligand-to-ligand charge transfer (LLCT). Solid-state diffuse reflectance data shows that there is a narrow optical band gap of 1.38?eV. Therefore, it could be probably a candidate for narrow band gap semiconductors. Graphic Abstract: A novel copper (II) complex is synthesized via solvothermal reactions, which is characteristic of an isolated structure, at the same time, it displays a wide and intense photoluminescence emission band in the pale blue region and theoretical study reveals that the photoluminescence emission is originated from the ligand-to-ligand charge transfer transition.[Figure not available: see fulltext.]
Yi, Xiu-Guang,Fang, Xiao-Niu,Wang, Yin-Feng,Guo, Jin,Li, Jia
p. 348 - 356
(2019/11/03)

Hydrothermal preparation, crystal structure, a series of properties and theoretical calculation of a novel cadmium compound
A novel cadmium compound [CdL(bipy)2]·6H2O was synthesized by hydrothermal method, and its crystal structure was determined by single-crystal X-ray diffraction. The title compound crystallized in the monoclinic system of the C2/c space group, and existed as an isolated monocyte structure. The strong π…π stacking interactions produces one-dimensional (1-D) chains and a three-dimensional (3-D) supramolecular structure is formed by a large number of intermolecular hydrogen bonds. A series of properties of the title compound were tested by solid state photoluminescence, CIE analysis and solid-state diffuse reflectance, and the charge transfer of the title compound was studied by time-dependent density functional theory.
Wang, Yin-Feng,Yi, Xiu-Guang,Fang, Xiao-Niu,Li, Jia,Xu, Yao,Xie, Shi-Kun
p. 1130 - 1136
(2020/03/16)

Preparation, photoluminescence, semiconductor properties, and theoretical calculations for a novel zinc zero-dimensional structure complex
The complex [Zn(CH3OH)4(MCA)2] (3-hydroxy-2-methylquinoline-4-carboxylic acid) has been synthesized through hydrothermal reactions and characterized by single-crystal X-ray diffraction. Its solid-state photoluminescence spectrum shows an emission in the blue region, which is assigned to ligand-to-metal charge transfer on the basis of time-dependent density functional theory calculations. Solid-state diffuse reflectance measurements show the existence of a narrow optical band gap of 1.73 eV.
Yi, Zhi-Qiang,Fang, Xiao-Niu,Cao, Zi-Yi,Wei, Yao,Li, Ya-Jing,Yi, Xiu-Guang
p. 58 - 62
(2019/06/03)

Synthesis and Ameliorative Effect of Isatin–Mesalamine Conjugates on Acetic Acid-induced Colitis in Rats
A series of new isatin–mesalamine conjugates (9a–g) were synthesized via conjugation of isatin (3a) and its derivatives (3b–3d, 4, 5, and 6) with mesalamine (7) by using chloroacetyl chloride as a bifunctional linker. Compounds 3a–3d were prepared by employing Sandmeyer reaction. Compounds 4, 5, and 6 were obtained from isatin (3a) via previously reported methods. The synthesized compounds were characterized by IR, mass, 1H NMR, and 13C NMR spectral techniques. Synthesized compounds (3a–d, 4, 5, 6, and 9a–g) were evaluated for in vitro antioxidant activity by DPPH assay method using ascorbic acid as standard. Hybrids 9b (IC50?=?368.6?±?3.5?μM) and 9f (IC50?=?335.1?±?2.9?μM) showed better antioxidant activity than its parent compounds such as 3a (IC50?=?556.8?±?2.9?μM), 5 (IC50?=?511.9?±?3.6?μM), and 7 (IC50?=?768.9?±?2.7?μM). Acetic acid-induced ulcerative colitis in rat model was chosen to examine the antioxidant potential of the synthesized hybrids (9b and 9f) in the amelioration of ulcerative colitis. Colonic myeloperoxidase and malondialdehyde enzymes were used as biomarkers of anti-ulcerative colitis activity. In the present study, hybrids 9b and 9f reduced the levels of colonic myeloperoxidase and malondialdehyde enzymes significantly (p??0.05) when compared with control (colitic), at a dose (0.03?mM/12.5?mg/kg b.w. p.o.) (50%) less than that of its parent moieties mesalamine (0.16?mM/25?mg/kg) and isatin (0.16?mM/25?mg/kg). Thus, the molecular hybridization was proved to be significant in enhancing the activity of hybrids 9b and 9f by reducing the dose.
Panga, Shyam,Podila, Naveen Kumar,Ciddi, Veeresham
p. 956 - 967
(2019/02/14)

Design and development of Isatin-triazole hydrazones as potential inhibitors of microtubule affinity-regulating kinase 4 for the therapeutic management of cell proliferation and metastasis
Microtubule affinity-regulating kinase 4 (MARK4) is a potential drug target as the same is found to be over expressed in several types of cancers. In search of effective MARK4 inhibitors, we have synthesized and characterized Isatin-triazole hydrazones (9a-i) and evaluated their inhibitory potential. Of all the compounds, 9g showed better binding affinity and enzyme inhibition potential in sub micromolar range. Human serum albumin (HSA) binding assay suggested an easy transportation of 9g in blood stream due to its binding affinity. In vitro anticancer studies performed on MCF-7, MDA-MB-435s and HepG2 cells using 9g showed inhibition of cell proliferation and cell migration. Further, 9g induces apoptosis in these cancerous cells, with IC50 values of 6.22, 9.94 and 8.14 μM, respectively. Putatively, 9g seems to cause oxidative stress resulting in apoptosis. Functional assay of 9g with a panel of 26 kinases showed MARK4 specific profile. In conclusion, 9g seems to possess an effective inhibitory potential towards MARK4 adding an additional repertoire to anticancer therapeutics.
Aneja, Babita,Khan, Nashrah Sharif,Khan, Parvez,Queen, Aarfa,Hussain, Afzal,Rehman, Md. Tabish,Alajmi, Mohamed F.,El-Seedi, Hesham R.,Ali, Sher,Hassan, Md. Imtaiyaz,Abid, Mohammad
p. 840 - 852
(2019/01/04)

Indazole compounds and preparation method and application thereof
The invention provides indazole compounds and a preparation method and application thereof. A series of completely new small molecule PI3Kdelta inhibitors are designed and synthesized by using indazole as a structural mother nucleus, the PI3Kdelta kinase inhibitory activity test and MV-4-11 cell activity test of the compounds are carried out, and the indazole compounds exhibit better kinase subtype selectivity, and exhibit better in vitro proliferation inhibitory activity against tumor cell lines. The compounds can be used in the preparation of antitumor drugs and in the preparation of activedrugs for inhibiting PI3Kdelta kinase, and a new way is provided for the antitumor drug research. The raw materials are cheap and easy to obtain, the preparation method is simple, and the large-scaleproduction is suitable. The structural formula is as shown in the specification.
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Paragraph 0015-0016

(2019/09/14)

Synthesis of substituted tryptanthrin via aryl halides and amines as antitumor and anti-MRSA agents
The natural alkaloid, tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione), and its analogues are found to exhibit potent antitumor and anti-MRSA activities. An efficient and convenient method has been developed for the synthesis of tryptanthrin D-ring derivatives through the reaction of substituted tryptanthrins and secondary amines in moderate to good yields. Some of the new compounds exhibited antitumor activities against the human tumor cell lines A549, HCT116 and MDA-MB-231, with mean IC50 values at low micromolar levels. In addition, some of the compounds showed excellent anti-MRSA activities and were more effective than vancomycin, with MIC values of 0.31–1.25 μg/mL for Mu50,RN4220, and Newman strains.
Chen, Huan,Hou, Baolong,Liu, Jianli,Liu, Li,Ma, Xiumei,Wang, Cuiling,Wang, Jilin,Wang, Rui,Wang, Yinyin,Zheng, Xudong
(2019/11/13)

Facile synthesis of isatins by direct oxidation of indoles and 3-iodoindoles using NIS/IBX
A facile one-pot access to a broad range of isatins by direct oxidation of indoles using NIS/IBX reagent in DMSO at 25 °C in very good isolated yields is reported. It is shown by mechanistic investigations that a number of substituted indoles react rapidly with NIS in DMSO to produce intermediary 3-iodoindoles, which undergo oxidation subsequently to isatins with IBX.
Chandra, Ajeet,Yadav, Navin R.,Moorthy, Jarugu Narasimha
supporting information
p. 2169 - 2174
(2019/03/04)

Metal-free synthesis of benzimidazo[1,2-c]quinazolin-6-ones with indole and benzenediamine oxidized by I2/TBHP
A variety of benzimidazo[1,2-c]quinazolin-6-ones derivatives can be accessed in moderate to good yields under simple and metal-free reaction conditions using indoles and o-benzenediamines oxidized by iodine and TBHP. This procedure works in reasonable yields for different indoles as well as o-benzenediamines thus may provide a good synthesis of quinazolinones. A TBHP oxidized ring expansion reaction mechanism that explains the synthesis of benzimidazo[1,2-c]quinazolin-6-ones were reported.
Dai, Zhen,Li, Songhua,Li, Yunyi,Feng, Lei,Ma, Chen
supporting information
p. 2012 - 2017
(2019/02/20)

MnO2?Fe3O4 Magnetic Nanoparticles as Efficient and Recyclable Heterogeneous Catalyst for Benzylic sp3 C?H Oxidation
Herein, we report a highly chemoselective and efficient heterogeneous MnO2?Fe3O4 MNP catalyst for the oxidation of benzylic sp3 C?H group of ethers using TBHP as a green oxidant to afford ester derivatives in high yield under batch/continuous flow module. This catalyst was also effective for the benzylic sp3 C?H group of methylene derivatives to furnish the ketone in high yield which can be easily integrated into continuous flow condition for scale up. The catalyst is fully characterized by spectroscopic techniques and it was found that 0.424 % MnO2?Fe3O4 catalyzes the reaction; the magnetic nanoparticles of this catalyst could be easily recovered from the reaction mixture. The recovered catalyst was recycled for twelve cycles without any loss of the catalytic activity. The advantages of MnO2?Fe3O4 MNP are its catalytic activity, easy preparation, recovery, and recyclability, gram scale synthesis with a TOF of up to 14.93 h?1 and low metal leaching during the reaction.
Pandey, Akanksha M.,Agalave, Sandip G.,Vinod, Chathakudath P.,Gnanaprakasam, Boopathy
supporting information
p. 3414 - 3423
(2019/10/19)

Iron-Catalyzed Cross-Dehydrogenative Coupling of Oxindoles with Thiols/Selenols for Direct C(sp3)?S/Se Bond Formation
The C?X (S/Se) bonds are common and ubiquitous in natural products and pharmaceuticals. Here, we report an iron-catalyzed cross-dehydrogenative coupling (CDC) reaction for the direct synthesis of C(sp3)?X (S/Se) bonds from oxindoles, phenylacetamides, pyrazolones, phenylacetonitriles and ethyl cyanoacetate with thiols and selenols. All the reactions were performed under simple and mild conditions, and air (molecular oxygen) was employed as an ideal green oxidant, thus promising broad application in chemical industry and modification of bioactive molecules. (Figure presented.).
Huang, Lu-Shan,Han, Dong-Yang,Xu, Da-Zhen
p. 4016 - 4021
(2019/07/18)

Organocatalytic Synthesis of Benzazetidines by Trapping Hemiaminals with Protecting Groups
Benzazetidines are highly strained and inherently unstable heterocycles. There are only few methodologies for assembling these compounds. Here, a protocol is presented to trap an elusive cyclic, four-membered hemiaminal structure. This method affords several benzazetidines in moderate to good yields (up to 81%), and it uses inexpensive materials and does not require catalysts based on transition metals. The high ring strain energy of these benzazetidine systems was estimated by density functional theory calculations to be about 32 kcal mol-1. This synthesis can be applied also on gram scale with reaction yield essentially unchanged.
Salvio, Riccardo,Placidi, Simone,Sinibaldi, Arianna,Di Sabato, Antonio,Buscemi, Dario C.,Rossi, Andrea,Antenucci, Achille,Malkov, Andrei,Bella, Marco
p. 7395 - 7404
(2019/06/07)

The Rearrangement of Peroxides for the Construction of Fluorophoric 1,4-Benzoxazin-3-one Derivatives
An unprecedented skeletal rearrangement of 3-(tert-butylperoxy)indolin-2-one using a tin catalyst has been developed. This rearrangement is highly selective to afford a series of fluorophoric (Z)-2-arylidene and alkylidene-2H-benzo[b][1,4]oxazin-3(4H)-one derivatives in good to excellent yield. In contrast with Sn(OTf)2, the reaction of 3-(tert-butylperoxy)indolin-2-one derivatives with FeCl3 afforded the Hock fragmentation product via C-C bond cleavage.
Chaudhari, Moreshwar B.,Chaudhary, Atul,Kumar, Vishnupriya,Gnanaprakasam, Boopathy
supporting information
p. 1617 - 1621
(2019/03/20)

A preparation method of the isatin (by machine translation)
A method for preparing a cement, to indigo as raw material, in a non-proton polar solvent in the judgement of the ozone oxidation isatin. Preparation method of this invention have high yield, and through the simple separation method can obtain high-purity isatin. The method avoids the traditional method as a result of the large amounts of heavy metals and sewage, and low cost, is extremely suitable for industrial production. (by machine translation)
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Paragraph 0021-0036

(2019/03/15)

Preparation, structure, photoluminescent and semiconductive properties, and theoretical calculation of a mononuclear nickel complex with 3-hydroxy-2-methylquinoline-4-carboxylato ligand
A novel nickel complex with mixed ligands [Ni(L)2(EtOH)2(MeOH)2] (HL = 3-hydroxy-2-methylquinoline-4-carbox-ylic acid) has been synthesized through solvothermal reaction and its crystal structure was determined by single-crystal X-ray diffraction technique. Single-crystal X-ray diffraction analyses reveals that the title compound crystallizes in the triclinic system of the P–1 space group, and exists as isolated mononuclear complex. The intermolecular hydrogen bonds lead to the formation of chains, and the layered supramolecular structure is formed by the strong π???π stacking interactions. Solid-state photoluminescent characterization reveals that the title compound has an emission in the green region. Time-dependent density functional theory (TDDFT) calculation shows that the nature of the photoluminescence of the title compound originates from the ligand-to-ligand charge transfer (LLCT; from the HOMO of the p-orbital of ligand HMCA to the LUMO of the oxygen atoms). A wide optical band gap of 2.25 eV is found by the solid-state UV/vis diffuse reflectance spectrum.
Fang, Xiao-Niu,Li, Jia,Yi, Xiu-Guang,Luo, Qi,Chen, Jia-Yi,Li, Yong-Xiu
p. 414 - 420
(2019/07/12)

A process for preparing isatin derivatives from substituted aniline
A process for preparing isatin derivatives from substituted aniline is provided. The process includes preparing isatin derivatives with a high yield from substituted aniline shown as a formula II anda carbonylation agent shown as a formula III through acid catalytic oxidation. Compared with traditional processes, the process has characteristics of cheap raw materials, simple and convenient operation, mild reaction conditions, a high product yield, high product purity, wide applicability, and the like, and is environmentally friendly. In addition, the process does not adopt a noble metal catalyst or ligand, so that heavy metal pollution is avoided and the process is suitable for industrial production.
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Paragraph 0066; 0067

(2019/06/12)

METHOD FOR PRODUCING ISATIN COMPOUND
PROBLEM TO BE SOLVED: To provide a method for producing an isatin compound useful as raw materials for various medical and agrochemical products and dyes, in high yield, with high purity, at low cost, and by simple operation. SOLUTION: An method for producing an isatin compound includes the reaction of an isonitrosoacetanilide compound represented by formula (1) at 15-60°C with sulfuric acid of 75% or more in concentration [R is H, a halogen atom or a linear/branched/cyclic alkyl group; n is an integer of 1-4]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0023; 0035

(2018/11/10)

Design, Synthesis, Characterization, and In Vitro Evaluation of Isatin-Pomalidomide Hybrids for Cytotoxicity against Multiple Myeloma Cell Lines
Inspired by the concept of molecular hybridization, a series of new isatin-pomalidomide hybrids (9a–9g) were designed, synthesized, characterized, and evaluated for in vitro cytotoxic activity against U266B1 and RPMI 8226 multiple myeloma cell lines. Sandmeyer methodology and N-halomethylketo alkylation reaction are the two important reactions involved in the synthesis of isatin-pomalidomide hybrids (9a–9g). All the synthesized compounds (3a–3d, 4, 5, 6, and 9a–9g) were characterized by using IR, mass, 1H-NMR, and 13C-NMR spectral techniques. The efficacy of all the synthesized compounds was tested against the aforementioned cell lines by employing MTT assay (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) standard protocols while using pomalidomide as a standard. The test concentrations used in the MTT assay were 1, 10, 20, 30, and 40?μM, and the period of incubation was 24?h. All the synthesized compounds were found to have moderate to greater cytotoxic activity against the aforementioned cell lines. Among them, synthesized hybrids 9f (IC50, U266B1?=?5.15?±?0.72?μM, RPMI8226?=?11.66?±?0.79?μM) and 9g (IC50, U266B1?=?2.50?±?0.37?μM, RPMI8226?=?6.70?±?0.55?μM) displayed better cytotoxic activity against both the cell lines used in the present study.
Panga, Shyam,Podila, Naveen Kumar,Ciddi, Veeresham
p. 2919 - 2928
(2018/10/26)

Design, synthesis and QSAR study of novel isatin analogues inspired Michael acceptor as potential anticancer compounds
Molecular hybridization is considered as an effective tactic to develop drugs for the treatment of cancer. A series of novel hybrid compounds of isatin and Michael acceptor were designed and synthesized on the basis of association principle. These hybrid compounds were tested for cytotoxic potential against human cancer cell lines namely, BGC-823, SGC-7901 and NCI-H460 by MTT assay. Most compounds showed good anti-growth activities in all tested human cancer cells. SAR and QSAR analysis may provide vital information for the future development of novel anti-cancer inhibitors. Notably, compound 6a showed potent growth inhibition on BGC-823, SGC-7901 and NCI-H460 with the IC50 values of 3.6 ± 0.6, 5.7 ± 1.2, 3.2 ± 0.7 μM, respectively. Besides, colony formation assays, wound healing assays and flow cytometry analysis indicated 6a exhibited a potent anti-growth and anti-migration ability in a concentration-dependence manner through arrested cells in the G2/M phase of cell cycle. Moreover, 6a significantly repressed tumor growth in a NCI-H460 xenograft mouse model. Overall, our findings suggested isatin analogues inspired Michael acceptor may provide promising lead compounds for the development of cancer chemotherapeutics.
Wang, Jiabing,Yun, Di,Yao, Jiali,Fu, Weitao,Huang, Fangyan,Chen, Liping,Wei, Tao,Yu, Cuijuan,Xu, Haineng,Zhou, Xiaoou,Huang, Yanqing,Wu, Jianzhang,Qiu, Peihong,Li, Wulan
p. 493 - 503
(2018/01/01)

Application of isatin analogues in preparing antineoplastic drugs
The invention belongs to the field of medicinal chemistry, and in particular relates to an application of isatin analogues in preparing antineoplastic drugs. A series of isatin analogues can be synthesized by splicing isatin and [alpha],[beta]-unsaturated ketone via a medicinal chemistry splicing principle. The compounds (the isatin analogues) are relatively good in inhibitory activity on three tumor cells, and an antineoplastic effect can be achieved by inhibiting growth and migration of tumor cells and by blocking cell cycle G2/M period; and based upon in vivo experimental results, it is also indicated that the compounds can inhibit tumor growth.
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Paragraph 0033; 0034

(2018/07/30)

Synthesis and cytotoxic studies of novel 5-phenylisatin derivatives and their anti-migration and anti-angiogenic evaluation
A number of 5-arylisatin derivatives were synthesized in 5–6 steps from readily available starting materials. Their structures were confirmed by 1H NMR and 13C NMR as well as LC/MS. The cytotoxicity of these novel isatins against human leukemia K562 cells were evaluated by MTT assay in vitro. SAR studies indicated that the N-substituted benzyl and C-5 substituted phenyl groups greatly enhance their cytotoxic activity, whereas an intact carbonyl functionality on C-3 present in the parent ring is required to maintain such a potency. Particularly, N-(p-methoxybenzyl)-5-(p-methoxyphenyl)isatin (compound 2m) showed the highest antitumor activity against K562 cell lines (IC50 = 0.03 μM). Moreover, treatment with compound 2m significantly inhibited liver cancer HepG2 cells proliferation and migration, which could also reduce the human umbilical vein endothelial cells (HUVEC) tube formation. In conclusion, compound 2m exhibited very good cancer cells proliferation inhibition by angiogenesis responses in vitro, and 2m might be a promising angiogenesis inhibitor for cancer treatment.
Zhang, Qian,Teng, Yuou,Yuan, Yuan,Ruan, Tingting,Wang, Qi,Gao, Xing,Zhou, Yao,Han, Kailin,Yu, Peng,Lu, Kui
p. 800 - 814
(2018/07/29)

Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles
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
supporting information
p. 7622 - 7632
(2018/06/22)

Copper-Catalyzed Oxidative Dimerization of 2-Oxindoles under Base-Free Conditions
A practical copper-catalyzed oxidative dimerization of 2-oxindoles using di- tert -butyl peroxide as the radical initiator under base-free conditions was achieved, which not only provided an efficient route to prepare various 3,3′-bioxindoles, but also represented a simple strategy for C(sp 3)-H functionalization/C-C bond formation. A radical mechanism was proposed based on the reaction results and controlling experiments.
Huang, Yi-Ling,Bao, Wen-Hui,Ying, Wei-Wei,Chen, Wei-Ting,Gao, Le-Han,Wang, Xin-Ye,Chen, Gan-Ping,Ge, Guo-Ping,Wei, Wen-Ting
supporting information
p. 1485 - 1490
(2018/05/25)

An efficient synthesis of versatile synthon 3-chlorooxindoles with NaCl/oxone
The present work describes an expedient approach for the direct conversion of indole-3-carboxaldehyde to 3-chlorooxindoles using a simple sustainable synthetic method. From an environmental perspective, a combination of NaCl/oxone in a CH3CN?:?H2O (1?:?1) system was developed for direct oxidative chlorination of a wide array of indole derivatives. This chlorination strategy is more viable, remarkably cheaper and provides easy access to potential 3-chlorooxindoles. In addition, this environmentally benign method can also be applicable for constructing isatin derivatives in good yields.
Lakshmi Reddy, Vanammoole,Prathima, Parvathaneni Sai,Rao, Vaidya Jayathirtha,Bikshapathi, Raktani
p. 20152 - 20155
(2018/12/13)

Method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid
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; 0060

(2018/09/08)

Palladium-Catalyzed Oxidation of Indoles to Isatins by tert -Butyl Hydroperoxide
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
supporting information
p. 969 - 973
(2018/02/09)

Excitation-wavelength-dependent photoluminescence of silicon nanoparticles enabled by adjustment of surface ligands
We herein present pioneering studies to reveal that excitation-wavelength-dependent photoluminescence properties of fluorescent silicon nanoparticles (SiNPs) can be realized by rationally designing surface ligands, i.e., several kinds of oxidized indole d
Shen, Xiao-Bin,Song, Bin,Fang, Bei,Jiang, Ai-Rui,Ji, Shun-Jun,He, Yao
supporting information
p. 4947 - 4950
(2018/05/23)

Synthesis of Indoline-2,3-diones by Radical Coupling of Indolin-2-ones with tert-Butyl Hydroperoxide
A novel strategy has been developed for the synthesis of indoline-2,3-diones through a metal-free radical-coupling reaction. Alkyl radicals derived from indolin-2-ones through a radical-transfer reaction combine with the tert-butylhydroperoxy radical readily generated from commercially available tert-butyl hydroperoxide to afford 3-(tertbutylperoxy)indolin-2-one intermediates that can be further transformed into indoline-2,3-diones under air. This strategy provides a simple and e?cient route to the construction of a C=O bond without the use of any metal catalyst or base.
Ying, Wei-Wei,Zhu, Wen-Ming,Liang, Hongze,Wei, Wen-Ting
supporting information
p. 215 - 218
(2017/09/28)

C(sp 3)-H Peroxidation of 3-Substituted Indolin-2-ones under Metal-Free Conditions
A C(sp 3)-H peroxidation of 3-substituted indolin-2-ones through radical coupling reaction has been developed under metal-free conditions. Using tert -butyl hydroperoxide both as an oxidant and as a peroxidation reagent to couple with the C(sp 3)-H bonds of 3-substituted indolin-2-ones can form a new C-O bond without using any additives. This simple strategy provides a green and efficient approach to 3-peroxyindolin-2-ones in moderate to excellent yields. The resulting 3-peroxyindolin-2-ones could be further transformed into 3-hydroxyindolin-2-ones.
Ying, Wei-Wei,Zhu, Wen-Ming,Gao, Zhanghua,Liang, Hongze,Wei, Wen-Ting
supporting information
p. 663 - 667
(2017/12/26)

NaI-mediated divergent synthesis of isatins and isoindigoes: A new protocol enabled by an oxidation relay strategy
A new approach for the synthesis of isatins and isoindigoes by an inexpensive and environmentally friendly NaI-mediated transformation is disclosed. The selectivity could be switched by simply varying the solvent, and isatins (using THF) and isoindigoes (using DMSO) could be obtained in moderate to excellent yields.
Zhang, Hong-Hua,Wang, Yong-Qiang,Huang, Long-Tao,Zhu, Long-Qing,Feng, Yi-Yue,Lu, Ying-Mei,Zhao, Quan-Yi,Wang, Xue-Qiang,Wang, Zhen
supporting information
p. 8265 - 8268
(2018/07/29)

Generation and Reactivity of Electron-Rich Carbenes on the Surface of Catalytic Gold Nanoparticles
The reactive nature of carbenes can be modulated, and ultimately reversed, by receiving additional electron density from a metal. Here, it is shown that Au nanoparticles (NPs) generate an electron-rich carbene on surface after transferring electron density to the carbonyl group of an in situ activated diazoacetate, as assessed by Fourier transformed infrared (FT-IR) spectroscopy, magic angle spinning nuclear magnetic resonance (MAS NMR), and Raman spectroscopy. Density functional theory (DFT) calculations support the observed experimental values and unveil the participation of at least three different Au atoms during carbene stabilization. The surface stabilized carbene shows an extraordinary stability against nucleophiles and reacts with electrophiles to give new products. These findings showcase the ability of catalytic Au NPs to inject electron density in energetically high but symmetrically allowed valence orbitals of sluggish molecules.
Oliver-Meseguer, Judit,Boronat, Mercedes,Vidal-Moya, Alejandro,Concepción, Patricia,Rivero-Crespo, Miguel ángel,Leyva-Pérez, Antonio,Corma, Avelino
supporting information
p. 3215 - 3218
(2018/03/13)

Assessment of 5-substituted Isatin as Surface Recognition Group: Design, Synthesis, and Antiproliferative Evaluation of Hydroxamates as Novel Histone Deacetylase Inhibitors
Histone deacetylase (HDAC) is a promising target for cancer treatment. HDAC inhibitors consist of three pharmacophoric features: an aromatic cap group, zinc binding group (ZBG), and a linker chain connecting cap group to ZBG. Herein, we report on (i) substituted isatin moiety as the cap group that recognizes the surface of active enzyme pocket and (ii) thiosemicarbazide moiety incorporated as linker group responsible for connecting the cap group to ZBG (hydroxamic acid). The synthesized compounds were evaluated for their antiproliferative activity and HDAC enzyme inhibition. The binding mode analysis of proposed compounds was evaluated by docking studies. Several analogs were found to inhibit HDAC and cellular proliferation of Hela cervical cancer cells, with GI50 values in the micromolar range. One compound (Vd) was found to have greater in vitro antiproliferative activity in comparison to other compounds.
Singh, Avineesh,Raghuwanshi, Kamlesh,Patel, Vijay K,Jain, Deepak K,Veerasamy, Ravichandran,Dixit, Anshuman,Rajak, Harish
p. 366 - 374
(2017/09/27)

Semicarbazone derivatives and use thereof
The invention belongs to the technical field of medicine, and relates to semicarbazone derivatives disclosed as general formula I, and geometrical isomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein the substituent groups M, R1, R2, R and n are defined in the specification. The invention also relates to a method for preparing compounds disclosed as Formula I, a pharmaceutical composition containing the compounds and application of the compounds and pharmaceutical composition in preparing drugs for treating and/or preventing cancers and other hyperplastic diseases.
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Paragraph 0570; 0571; 0575; 0576;

(2017/08/14)

First asymmetric reduction of isatin by marine-derived fungi
In this study, whole cells of marine-derived fungi were used to reduce isatin (1H-indole-2,3-dione) to dioxindole (3-hydroxyindolin-2-one) for 7 days at 32°C. The screening showed that several strains could reduce isatin and produce the enantioenriched dioxindole. The best conversions were obtained by Cladosporium sp. CBMAI 1237 and Westerdykella sp. CBMAI 1679, however, the best enantiomeric excess was obtained only by Aspergillus sydowii CBMAI 935 (66percent ee). In conclusion, marine-derived fungi show potential for asymmetric and chemoselective reduction of isatin (1H-indole-2,3-dione).
Birolli, Willian G.,Ferrreira, Irlon M.,Jimenez, David E. Q.,Silva, Bianca N. M.,Silva, Bárbara V.,Pinto, Angelo C.,Porto, André L. M.
p. 1023 - 1029
(2017/05/01)

Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipole and Abnormal [3 + 2]-Cycloaddition with Maleimide in the Presence of 1,4-Diazabicyclo[2.2.2]octane
A new isatin N,N′-cyclic azomethine imine synthon was devised, and an unexpected abnormal [3 + 2]-cycloaddition with maleimide catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) has been disclosed. A variety of tricyclic spiropyrrolidine oxindoles bearing a dinitrogen heterocycle and succinimide scaffold were obtained in excellent yields (up to 96%) and diastereoselectivities (up to 97:3) under mild conditions.
Wang, Xiao,Yang, Peng,Zhang, Yong,Tang, Chao-Zhe,Tian, Fang,Peng, Lin,Wang, Li-Xin
supporting information
p. 646 - 649
(2017/02/10)