- Structure and Isomerism of 2-(3-Substituted) Quinoxalinylhydrazones of Isatin and Its Homologs
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Mono- and dihydrazones, the structure of which were established by means of 1H and 13C NMR, IR, and electronic absorption spectroscopy, were synthesized by reaction of 3-chloro-2-hydrazino- and 2,3-dihydrazinoquinoxalines with 1H-indole-2,3-dione and its 1-methyl and 1-butyl homologs.Thermal and photochemical conversion of the E, Z isomer to the Z isomer is observed, while the reverse transformation is observed in the case of treatment with alkali.
- Dziomko, V. M.,Stopnikova, M. N.,Shmelev, L. V.,Ryabokobylko, Yu. S.,Adamova, G. M.,Poponova, R. V.
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- Selective "naked eye" detection of Al(iii) and PPi in aqueous media on a rhodamine-isatin hybrid moiety
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A highly selective fluorescence probe, RIH (rhodamine-isatin hybrid) for Al3+ has been designed and synthesized. This new dual signal (colorimetric and fluorogenic "off-on" type) chemosensing ensemble based on the complex between RIH and Al3+ has also been effective to selectively discriminate PPi from other anions in aqueous solution at physiological pH. The Royal Society of Chemistry 2013.
- Goswami, Shyamaprosad,Paul, Sima,Manna, Abhishek
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- Thiophene-functionalized octupolar triindoles: Synthesis and photophysical properties
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Two thiophene-functionalized octupolar triindole molecules were synthesized through Suzuki and Sonogashira cross-coupling reactions. Their photophysical and electrochemical properties were explored. The spectroscopic data demonstrate that triindole is an
- Yuan, Mao-Sen,Li, Tian-Bao,Wang, Wen-Ji,Du, Zhen-Ting,Wang, Jun-Ru,Fang, Qi
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- Rongalite-induced transition-metal and hydride-free reductive aldol reaction: a rapid access to 3,3′-disubstituted oxindoles and its mechanistic studies
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A transition-metal and hydride-free reductive aldol reaction has been developed for the synthesis of biologically active 3,3′-disubstituted oxindoles from isatin derivatives using rongalite. In this protocol, rongalite plays a dual role as a hydride-free
- Anugu, Naveenkumar,Golla, Sivaparwathi,Jalagam, Swathi,Kokatla, Hari Prasad
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supporting information
p. 808 - 816
(2022/02/03)
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- Fluorine-substituted indolo-thiadiazoloquinoxaline-based D-A type polymers for photovoltaic applications
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Two D-A type conjugated polymers, in which the electron-donating benzodithiophene monomers are connected to the electron-accepting indolo-thiadiazoloquinoxaline (ITQ) monomers via a thiophene bridge, are synthesized under Stille coupling conditions. Once the reference PB-ITQ is prepared, one fluorine atom is incorporated into the ITQ unit of PB-ITQ to afford the additional target polymer PB-ITQF. An inverted-type device with the configuration of indium tin oxide (ITO)/ZnO/Polymer:PC71BM/MoO3/Ag is utilized to examine the photovoltaic properties of the two polymers. Owing to the positive contributions of fluorine atoms, all the photovoltaic parameters of the device based on PB-ITQF such as the short-circuit current density, open-circuit voltage, and fill factor are improved as compared with those of the device based on PB-ITQ. As a result, the highest PCE of 2.32% is achieved from the fullerene-based polymer solar cell based on PB-ITQF.
- Lee, Seok Woo,Lee, Jun Ho,Kim, Joo Hyun,Chang, Dong Wook
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- Isatin-linked 4,4-dimethyl-5-methylene-4,5-dihydrothiazole-2-thiols for inhibition of acetylcholinesterase
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A series of novel isatin-linked 4,4-dimethyl-5-methylene-4,5-dihydrothiazole-2-thiols (IT2Ts) 1a–1g were designed as acetylcholinesterase (AChE) inhibitors capable of interacting with both the catalytic active site (CAS) and peripheral anionic site (PAS) of the enzyme simultaneously. The target IT2Ts were prepared through a short synthesis in moderate yield. The most potent inhibitors of this series 1b and 1c (IC50 = 18.2 and 27.5 μM, respectively) outperformed rivastigmine and were comparable to galantamine, both clinically used AChE inhibitors. Furthermore, 1b displayed non-competitive inhibition patterns in kinetic studies, whereas molecular modeling predicted a simultaneous interaction with both the CAS and PAS. In silico methods predicted several promising drug-like characteristics of 1b. Taken together, these results indicate 1b warrants further investigation as a multitarget-directed ligand for AChE inhibition. [Figure not available: see fulltext.]
- Davis, Sydney M.,Eckroat, Todd J.
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p. 2289 - 2300
(2021/10/25)
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- Palladium-Catalyzed Cascade Hydrosilylation and Amino-Methylation of Isatin Derivatives
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We demonstrate that using palladium acetate as a catalyst for reduction of DMF and isatin derivatives by hydrosilanes, a cascade hydrosilylation and amino-methylation reaction can be realized. With DMF as a reactant and a solvent, the in-situ generated siloxymethylamine intermediate, an adduct of DMF and hydrosilanes, smoothly participates in the successive stages, providing a serials of Si, N-functionalized indolin-2-ones in moderate to good yields. This strategy exhibits high chemoselectivity toward carbonyl moieties reduction among the substrates. (Figure presented.).
- Liu, Yue,Xia, Yun-Tao,Cui, Su-Hang,Ji, Yi-Gang,Wu, Lei
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supporting information
p. 2632 - 2636
(2020/06/02)
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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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- 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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- Synthesis of isatin based N1-alkylated 3-β-C-glycoconjugated-oxopropylidene oxindoles as potent antiplasmodial agents
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In an attempt to develop new antimalarial drugs, we have synthesized a new class of N-alkylated 3-glycoconjugated-oxopropylidene oxindoles starting from substituted isatins and glucopyranosyl propanone via a well-known cross-aldol reaction followed by deh
- Thakur, Ravi Kumar,Joshi, Prince,Upadhyaya, Kapil,Singh, Kartikey,Sharma, Gaurav,Shukla, Sanjeev K.,Tripathi, Renu,Tripathi, Rama Pati
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supporting information
p. 448 - 454
(2018/11/25)
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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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- Novel hydrazido benzenesulfonamides-isatin conjugates: Synthesis, carbonic anhydrase inhibitory activity and molecular modeling studies
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As a part of our ongoing efforts towards developing novel carbonic anhydrase inhibitors based on the isatin moiety, herein we report the synthesis and biological evaluation of novel sulfonamides (5a-h, 10a-g and 11a-c) incorporating substituted 2-indolinone moiety (as tail) linked to benzenesulfonamide (as zinc anchoring moiety) through a hydrazide linker. 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, IX and XII. All these isoforms were inhibited by the sulfonamides reported here in variable degrees. hCA I was inhibited with KIs in the range of 671.8: 3549.5 nM, hCA II in the range of 36.8: 892.4 nM; hCA IX in the range of 8.9: 264.5 nM, whereas hCA XII in the range of 9.0: 78.1 nM. In particular, compound 10b emerged as a single-digit nanomolar hCA IX and XII inhibitor (8.9 and 9.2 nM, respectively). Molecular docking studies carried out for compound 10b within the hCA II, IX and XII active sites allowed us to rationalize the obtained inhibition results.
- Abo-Ashour, Mahmoud F.,Eldehna, Wagdy M.,Nocentini, Alessio,Ibrahim, Hany S.,Bua, Silvia,Abou-Seri, Sahar M.,Supuran, Claudiu T.
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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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- Copper-catalyzed aerobic oxidative intramolecular amidation of 2-aminophenylacetylenes: A domino process for the synthesis of isatin
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A novel CuI-catalyzed oxidative amidation of 2-aminophenylacetylenes leading to the formation of isatins by using open air as an oxygen source has been developed. The reaction proceeded smoothly and provided a variety of isatin derivatives in good yields. The advantages of this one-pot reaction protocol include the use of a green oxidant, low-price catalyst and facile conditions, and easy handling.
- Salvanna,Ramesh, Perla,Santosh Kumar,Das, Biswanath
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p. 13754 - 13759
(2017/11/27)
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- Double Carbonylation Using Glyoxal (HCOCOH): A Practical Copper-Promoted Synthesis of Isatins from Primary and Secondary Anilines
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A novel double carbonylation process has been demonstrated with easily available HCOCOH (glyoxal) as the double carbonylation reagent. Simple CuCl2?2H2O (copper(II) chloride dihydrate) was used as the oxidant for this transformation. Under optimized reaction conditions, various primary and secondary anilines were double-carbonylated to afford their corresponding isatins (26 examples, up to 80% yields). (Figure presented.).
- Kuan, Suzie Hui Chin,Sun, Wei,Wang, Lu,Xia, Chungu,Tay, Meng Guan,Liu, Chao
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supporting information
p. 3484 - 3489
(2017/09/06)
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- IBX-promoted domino reaction of α-hydroxy amides: A facile one-pot synthesis of isatins
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A novel and temperature-controlled oxidation of α-hydroxy amides in the presence of IBX is described. The divergent one-pot synthesis of isatins and α-formyl amides was achieved in good to excellent yields under metal-free conditions. And these two mild methods can tolerate a variety of functional groups, and are operationally simple.
- Wang, Yaoling,Cheng, Xu,Zhan, Zhen,Ma, Xiaojun,Nie, Ruifang,Hai, Li,Wu, Yong
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p. 2870 - 2874
(2016/01/16)
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- Ru(III)-mediated intramolecular ortho-C(sp2)-H activation/oxidative acylation: One-pot synthesis of isatins from α-hydroxy amides
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A novel and efficient synthesis of isatins from α-hydroxy amides via ruthenium-mediated aromatic C-H activation is described. The reactions proceeded smoothly under mild conditions and generated the corresponding products in good to excellent yields. This methodology has a broad substrate scope and opens up an interesting and attractive avenue for the application of intramolecular ortho-C-H activation.
- Wang, Yaoling,Li, Weijian,Cheng, Xu,Zhan, Zhen,Ma, Xiaojun,Guo, Li,Jin, Hui,Wu, Yong
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p. 3193 - 3197
(2016/05/24)
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- Hydrogen Peroxide Promoted Metal-Free Oxidation/Cyclization of α-Hydroxy N-Arylamides: A Facile One-Pot Synthesis of Isatins
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A novel, efficient, and environmentally friendly method was developed for converting α-hydroxy N-arylamides into isatins (1H-indole-2,3-diones) by using hydrogen peroxide as oxidant. The reactions proceeded smoothly under metal-free conditions and generated the corresponding products in good to excellent yields. This method has advantages of a broad substrate scope and simple operations.
- Li, Jie,Cheng, Xu,Ma, Xiaojun,Lv, Guanghui,Zhan, Zhen,Guan, Mei,Wu, Yong
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supporting information
p. 2485 - 2488
(2016/10/25)
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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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p. 532 - 543
(2016/08/12)
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- Ferric(III) chloride catalyzed intramolecular cyclization of N-alkyl-2-oxo-acetanilides: A facile access to isatins
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A facile strategy for the synthesis of isatins in high yield from N-alkyl-2-oxo-acetanilides has been developed via Friedel-Crafts alkylation using FeCl3 as catalyst under air. This reaction proceeds through direct intramolecular addition and oxidation in one pot. Also this methodology is operationally simple, atom economical, and environment friendly.
- Zheng, Yang,Li, Jue,Yu, Xinling,Lv, Songyang,Hai, Li,Wu, Yong
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supporting information
p. 39 - 42
(2015/12/24)
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- First Report on the Synthesis of Isatins via Pyridinium Chlorochromate Catalyzed Intramolecular Cyclization Reactions
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A new and useful strategy to synthesize isatins from α-formyl amides has been developed via one-pot intramolecular cyclization-oxidation reaction with the present of pyridinium chlorochromate (PCC). The reaction proceeded smoothly under air and has good yields of the corresponding products. Also, this methodology has a broad substrate scope, and is operationally simple and atom economic.
- Yue, Qiming,Wang, Yaoling,Hai, Li,Guo, Li,Yin, Hongmei,Wu, Yong
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supporting information
p. 1292 - 1296
(2016/05/10)
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- A pharmaceutical intermediate indole -2,3-dione method for the preparation of compounds
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The invention relates to a method for preparing drug intermediate benzpyrole-2,3-diketone-class compounds. The novel compounded system of Cu(acac)/assistants is adopted in the method, and therefore the conversion rate and the reaction yield of materials are greatly improved, the reaction condition is obviously improved, and meanwhile an inventor performs beneficial screening on varieties of the assistants and reaction solvents. HSiEt2Me and 1-butyl-3-methylimidazole trifluoromethane sulfimide salt are the most suitable assistant combination, methylbenzene is the optimal reaction solvent, and the method has the quite wide industrial application prospect and the market value.
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Paragraph 0029 - 0032; 0048; 0054; 0059; 0063
(2018/02/04)
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- Triazino indole-quinoline hybrid: A novel approach to antileishmanial agents
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A novel series of 1,2,4-triazino-[5,6b]indole-3-thione covalently linked to 7-chloro-4-aminoquinoline have been synthesized and evaluated for their in vitro activity against extracellular promastigote and intracellular amastigote form of Leishmania donovani. Among all tested compounds, compounds 7a and 7b were found to be the most active with IC50 values 1.11, 0.36 μM and selectivity index (SI) values 67, >1111, respectively, against amastigote form of L. donovani which is several folds more potent than the standard drugs, miltefosine (IC50 = 8.10 μM, SI = 7) and sodium stibo-gluconate (IC50 = 54.60 μM, SI ≥ 7).
- Sharma, Rashmi,Pandey, Anand Kumar,Shivahare, Rahul,Srivastava, Khushboo,Gupta, Suman,Chauhan, Prem M.S.
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p. 298 - 301
(2015/06/01)
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- Design and synthesis of 3-substituted indolin-2-one derivatives with methyl (e)-2-(3-Methoxy) acrylate moiety
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In this article, fifteen indolin-2-one derivatives with methyl (E)-2-(3-methoxy)acrylate group were designed and synthesized. The structures of target compounds were confirmed by 1H NMR, IR and HR-MS spectra analysis.
- Luo, Xi,Zhang, Yi-Ying,Wang, Yu-Liang
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p. 2911 - 2916
(2015/12/11)
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- Synthesis of isatins by the palladium-catalyzed intramolecular acylation of unactivated aryl C(sp2)-H bonds
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Synthesis of isatins from formyl-N-arylformamides is achieved via PdCl2-catalyzed intramolecular acylation. This method shows the possibility of Pd-catalyzed aryl C(sp2)-H bond activation on the synthesis of isatins, affording an array of isatins in good yields. Yet this protocol is operationally simple and atom economical.
- Li, Jue,Zheng, Yang,Yu, Xinling,Lv, Songyang,Wang, Qiantao,Hai, Li,Wu, Yong
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p. 103280 - 103283
(2015/12/23)
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- 3-(2-oxoethylidene)indolin-2-one derivatives activate Nrf2 and inhibit NF-κB: Potential candidates for chemoprevention
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Induction of cytoprotective phase 2 enzymes through inhibition of Keap1, a repressor of transcription factor Nrf2, is a cancer-prevention strategy. Compounds that elicit antiinflammatory and cytoprotective effects are promising candidates for chemoprevent
- Nagle, Amrita A.,Reddy, Shridhivya A.,Bertrand, Helene,Tajima, Hisashi,Dang, Truong-Minh,Wong, Siew-Cheng,Hayes, John D.,Wells, Geoffrey,Chew, Eng-Hui
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supporting information
p. 1763 - 1774
(2014/08/18)
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- Design and synthesis of marine natural product-based 1H-indole-2,3-dione scaffold as a new antifouling/antibacterial agent against fouling bacteria
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Marine organisms such as seaweeds, sponges and corals protect their own surfaces from fouling by their high anesthetic, repellant, and settlement inhibition properties. Within the marine ecosystem, evolution has allowed for the development of certain antifouling properties. Isatin is a biologically active chemical produced by an Alteromonas sp. strain inhibiting the surface of embryos of the cardiean shrimp Palaemon macrodectylus, which protect them from the pathogenic fungus Lagenidium callinectes. In present study, an antibacterial activity of isatin and its synthetic analogues were evaluated against different fouling bacteria in order to explore the structure activity relationships for the first time. The synthesized compounds along with parent isatin were tested against different ecologically relevant marine microorganisms by using the Kirby-Bauer disc diffusion method. Few synthetically modified isatin exhibited potent inhibitory activity at concentration of 2 μg/disc against Planococcus donghaensis, Erythrobacter litoralis, Alivibrio salmonicida, Vibrio furnisii. Overall, the modified analogues showed stronger activity than the parent marine natural product (isatin) and hence 1H-indole-2,3-dione scaffold has immense potential as future antibacterial/antifouling candidate.
- Majik, Mahesh S.,Rodrigues, Cheryl,Mascarenhas, Stacey,D'Souza, Lisette
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- Design, synthesis and biological evaluation of N-alkyl or aryl substituted isoindigo derivatives as potential dual cyclin-dependent kinase 2 (CDK2)/glycogen synthase kinase 3β (GSK-3β) phosphorylation inhibitors
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A series of N-alkyl or aryl substituted isoindigo derivatives have been synthesized and their anti-proliferative activity was evaluated by Sulforhodamine B (SRB) assay. Some of the target compounds exhibited significant antitumor activity, including compounds 6h and 6k (against K562 cells), 6i (against HeLa cells) and 6j (against A549 cells). N-(p-methoxy-phenyl)-isoindigo (6k) exhibited a high and selective anti-proliferative activity against K562 cells (IC50 7.8 μM) and induced the apoptosis of K562 cells in a dose-dependent manner. Compound 6k arrested the cell cycle at S phase in K562 cells by decreasing the expression of cyclin A and CDK2, which played critical roles in DNA replication and passage through G2 phase. Moreover, compound 6k down-regulated the expression of p-GSK-3β (Ser9), β-catenin and c-myc proteins, up-regulated the expression of GSK-3β, consequently, suppressed Wnt/β-catenin signaling pathway and induced the apoptosis of K562 cells. The binding mode of compound 6k with GSK-3β was simulated using molecular docking tools. All of these studies gave a better understanding to the molecular mechanisms of this class of agents and clues to develop dual CDK2/GSK-3β (Ser9) phosphorylation inhibitors applied in cancer chemotherapy.
- Zhao, Ping,Li, Yanzhong,Gao, Guangwei,Wang, Shuai,Yan, Yun,Zhan, Xiaoping,Liu, Zenglu,Mao, Zhenmin,Chen, Shaoxiong,Wang, Liqun
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p. 165 - 174
(2014/09/17)
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- An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)-H oxidation and intramolecular C-N bond formation of 2′-aminoacetophenones
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A novel molecular I2-catalyzed synthesis of isatins through C(sp3)-H oxidation and intramolecular C-N bond formation of 2′-aminoacetophenones with excellent yields up to 97% under transition metal, base, additive, peroxide and ligand free conditions is described. The present protocol is suitable for gram scale synthesis of isatins and retained its high yield. Further, the synthetic utility of this present reaction towards synthesis of bioactive 3-hydroxy-2-oxindoles and oxindoles is demonstrated. This journal is
- Rajeshkumar, Venkatachalam,Chandrasekar, Selvaraj,Sekar, Govindasamy
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p. 8512 - 8518
(2014/12/10)
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- Direct amidation of 2'-aminoacetophenones using I2-TBHP: A unimolecular domino approach toward isatin and iodoisatin
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Synthesis of isatin and iodoisatin from 2'-aminoacetophenone was achieved via oxidative amido cyclization of the sp3 C-H bond using I 2-TBHP as the catalytic system. The reaction proceeds through sequential iodination, Kornblum oxidation, and amidation in one pot. This method is simple, atom economic, and works under metal- and base-free conditions.
- Ilangovan, Andivelu,Satish, Gandhesiri
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p. 4984 - 4991
(2014/06/23)
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- Synthesis of N-alkyl isatins via oxidative cyclization of N-alkyl 2-bromo(chloro)acetanilides
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A highly efficient method for the synthesis of N-alkyl isatins starting from N-alkyl 2-bromo or 2-chloro acetanilides is described. The starting materials are easy to prepare and the yields of isatins are generally high. Operationally the reaction is very simple to run. Even though best results were obtained with a catalytic amount of CuI, the reactions of N-alkyl 2-bromo acetanilides actually performed well even in the absence of any metal catalyst. the Partner Organisations 2014.
- Gui, Qingwen,Dai, Fenglin,Liu, Jidan,Chen, Peixing,Yang, Zhiyong,Chen, Xiang,Tan, Ze
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supporting information
p. 3349 - 3353
(2014/05/20)
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- Triazino indole-quinoline hybrid: A novel approach to antileishmanial agents
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A novel series of 1,2,4-triazino-[5,6b]indole-3-thione covalently linked to 7-chloro-4-aminoquinoline have been synthesized and evaluated for their in vitro activity against extracellular promastigote and intracellular amastigote form of Leishmania donovani. Among all tested compounds, compounds 7a and 7b were found to be the most active with IC50 values 1.11, 0.36 μM and selectivity index (SI) values 67, >1111, respectively, against amastigote form of L. donovani which is several folds more potent than the standard drugs, miltefosine (IC50 = 8.10 μM, SI = 7) and sodium stibo-gluconate (IC50 = 54.60 μM, SI ≥ 7).
- Sharma, Rashmi,Pandey, Anand Kumar,Shivahare, Rahul,Srivastava, Khushboo,Gupta, Suman,Chauhan, Prem M.S.
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p. 298 - 301
(2014/01/17)
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- ISATIN COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATMENT OF DEGENERATIVE DISEASES AND DISORDERS
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Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of degenerative diseases and disorders.
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Paragraph 0158; 0159; 0160; 0188; 0189
(2014/09/30)
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- Copper-catalyzed selective oxidative acylation of secondary anilines with ethyl glyoxalate: Domino synthesis of indoline-2,3-diones
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A novel, easy and useful copper-catalyzed selective acylation of secondary anilines with ethyl glyoxalate has been developed, and the corresponding indoline-2,3-dione derivatives were prepared. The procedure comprises the sequential intermolecular copper-catalyzed selective oxidative ortho-site aromatic acylation of the NH group in secondary anilines and intramolecular nucleophilic attack of the NH group to the ester. The inexpensive, easy and efficient method should provide a new strategy for synthesis of dicarbonyl compounds. Copyright
- Liu, Tao,Yang, Haijun,Jiang, Yuyang,Fu, Hua
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supporting information
p. 1169 - 1176
(2013/05/21)
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- Copper-catalyzed tandem oxidative cyclization of arylacetamides: Efficient access to N-functionalized isatins
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An efficient copper-catalyzed synthesis of N-substituted isatins has been developed in good yields from easily accessible arylacetamides. A wide range of electronically and structurally varied nitrogen fragments could be assembled through this tandem C-O/C-N bond-forming process by tuning the reaction conditions.
- Sun, Jie,Liu, Bingxin,Xu, Bin
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p. 5824 - 5827
(2013/05/09)
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- Synthesis and CDK2 kinase inhibitory activity of 7/7′-azaindirubin derivatives
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A series of novel 7′-azaindirubin (1a-g) and 7-azaindirubin (2a, 2c, 2e and 2f) derivatives were designed and synthesized. Their structures were characterized by 1H NMR and MS spectroscopy as well as by elemental analysis. Their inhibitory properties against CDK2/cylinA were evaluated in vitro. In contrast to indirubin, some of the described azaindirubins emerged as potent inhibitors of CDK2/cylinA and compound 2b had more potent activity. Biological tests also showed that nitrogen atom at 7-position of azaindirubin was more beneficial to enhance the kinase inhibitory activity.
- Wang, Zhao Hui,Dong, Ying,Wang, Tao,Shang, Ming Hong,Hua, Wei Yi,Yao, Qi Zheng
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scheme or table
p. 297 - 300
(2010/12/19)
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- HYDRAZONE MODULATORS OF CANNABINOID RECEPTORS
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Hydrazone compounds which modulate cannabinoid receptors are presented. Pharmaceutical compositions containing these compounds, methods of using these compounds as modulators of cannabinoid receptors and processes for synthesizing these compounds are also described herein.
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Page/Page column 45, 47
(2009/03/07)
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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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p. 831 - 840
(2008/09/18)
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- Design and synthesis of a novel series of N-alkyl isatin acylhydrazone derivatives that act as selective cannabinoid receptor 2 agonists for the treatment of neuropathic pain
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There is growing interest in using cannabinoid receptor 2 (CB2) agonists for the treatment of neuropathic pain. We have synthesized a novel series of N-alkyl isatin acylhydrazone derivatives and have identified and characterized several of them as novel analogues with high functional activity and selectivity at human CB2 receptors using [35S]GTP-γ-S assays. Binding affinities at human CB2 and CB1 were determined for compounds 28, 33, 40, 48, and 58. Structure-activity relationship studies of this novel series led to optimization of our lead compound, compound 33 (MDA19). Compound 33 possessed potent antiallodynic effects in a rat model of neuropathic pain but did not affect rat locomotor activity. More potent and more CB2-receptor-selective compounds, including compounds 37, 40, and 48, were also discovered.
- Diaz, Philippe,Xu, Jijun,Astruc-Diaz, Fanny,Pan, Hao-Min,Brown, David L.,Naguib, Mohamed
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supporting information; experimental part
p. 4932 - 4947
(2009/07/11)
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- A selective chromogenic molecular sensor for acetate anions in a mixed acetonitrile-water medium
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Quinonehydrazone compound 2, as a new chromogenic anion sensor, can selectively detect AcO- over F- and other anions in mixed acetonitrile-water media. The deprotonation of the N-H proton of the sensor is responsible for the drastic color change. An acidic C-H group in the receptor, probably acting as an accessorial binding site, is essential to the selectivity and affinity for sensing the acetate anions. The Royal Society of Chemistry 2008.
- Hu, Shuzhen,Guo, Yong,Xu, Jian,Shao, Shijun
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experimental part
p. 2071 - 2075
(2009/02/01)
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- Selective photo-reduction of 1-alkylisatins in degassed alcoholic solutions
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Irradiation of 1-alkylisatins (1) in degassed alcohols afforded 1-alkyl-3-hydroxyoxindoles (2) and 1-alkyloxindoles (3) as chemoselective photoproducts.
- Tatsugi, Jiro,Ikuma, Kenji,Izawa, Yasuji
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