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Subrata Mukherjee, Sumi Joseph, Anup Bhunia, Rajesh G Gonnade, Santhivardhana Reddy Yetra, Akkattu T Biju
The N-heterocyclic carbene (NHC)-catalyzed enantioselective formal [3 + 2] annulation of α,β-unsaturated aldehydes with 3-hydroxy oxindoles is presented. Under oxidative conditions using the bisquinone oxidant, the reaction resulted in the synthesis of spiro γ-butyrolactones in moderate to good yields, enantioselectivity and diastereoselectivity. The reaction likely proceeds via the generation of the NHC-bound α,β-unsaturated acylazolium intermediate from enals, which was intercepted by the dioxindoles in a formal [3 + 2] pathway to form the spirocyclic compounds...
February 15, 2017: Organic & Biomolecular Chemistry
Wagdy M Eldehna, Hadia Almahli, Ghada H Al-Ansary, Hazem A Ghabbour, Mohamed H Aly, Omnia E Ismael, Abdullah Al-Dhfyan, Hatem A Abdel-Aziz
Treatment of patients with triple-negative breast cancer (TNBC) is challenging due to the absence of well- defined molecular targets and the heterogeneity of such disease. In our endeavor to develop potent isatin-based anti-proliferative agents, we utilized the hybrid-pharmacophore approach to synthesize three series of novel isatin-based hybrids 5a-h, 10a-h and 13a-c, with the prime goal of developing potent anti-proliferative agents toward TNBC MDA-MB-231 cell line. In particular, compounds 5e and 10g were the most active hybrids against MDA-MB-231 cells (IC50 = 12...
December 2017: Journal of Enzyme Inhibition and Medicinal Chemistry
Titiksh L Devale, Jignesh Parikh, Pankaj Miniyar, Pankaj Sharma, Birendra Shrivastava, Prashant Murumkar
A novel series of substituted N-(2-(2,3-dioxoindolin-1-yl)acetyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide was designed, synthesized and evaluated for in vitro Reverse Transcriptase (RT) inhibitory activity. This series is a combination of peculiar structural features from leading scaffolds of [(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) and oxyindole. In vitro screening led to identification of two hybrids (9c and 9d) possessing higher RT inhibitory activity than the standard rilpivirine...
January 18, 2017: Bioorganic Chemistry
Moustafa T Gabr, Nadia S El-Gohary, Eman R El-Bendary, Mohamed M El-Kerdawy, Nanting Ni
A new series of isatin-β-thiocarbohydrazones was synthesized based on the pharmacophoric features of triapine required for metal chelation. Our strategy involved the modifications of triapine basic skeleton by replacing pyridinyl moiety with isatin which retains the tridentate feature of triapine needed for metal chelation. The new compounds were esteemed for their antitumor efficacy against cervical cancer (Hela) and kidney fibroblast cancer (COS-7) cell lines. Compounds 4c, 4d, 5c and 5e exhibited remarkable efficacy against Hela cell line...
January 23, 2017: European Journal of Medicinal Chemistry
Gehad Lotfy, Mohamed M Said, El Sayed H El Ashry, El Sayed H El Tamany, Abdullah Al-Dhfyan, Yasmine M Abdel Aziz, Assem Barakat
The 1,3-dipolar cycloadditions of an azomethine ylide generated from isatin and thiazolidinecarboxylic acid to a series of 2,6-bis[(E)-arylmethylidene]cyclohexanones afforded new di-spiro heterocycles incorporating pyrrolidine and oxindole rings in quantitative yields and chemo-, regio-, and stereoselectively. The newly synthesized compounds were characterized using spectroscopic techniques. Furthermore, the molecular structures of 4a, 4e, and 4n were confirmed by X-ray crystallography. These newly synthesized compounds were screened for their in vitro activity against breast cancer cell line MCF-7 and K562-leukemia...
January 16, 2017: Bioorganic & Medicinal Chemistry
Xiao Wang, Peng Yang, Yong Zhang, Chao-Zhe Tang, Fang Tian, Lin Peng, Li-Xin Wang
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.
January 23, 2017: Organic Letters
Jing Sun, Guo-Liang Shen, Ying Huang, Chao-Guo Yan
The triethylamine promoted three-component reaction of N-(4-nitrobenzyl), N-ethoxycarbonylmethylisoquinolinium bromide, isatins and malononitrile in ethanol afforded spiro[indoline-3,2'-pyrrolo[2,1-a]isoquinolines] in good yields and with high diastereoselectivity. The similar reaction of N-cyanomethylisoquinolinium chloride mainly gave complex indolo[2″,3″:2',3']pyrrolo[3',4':4,5]pyrrolo[2,1-a]isoquinoline derivatives. However, the three-component reaction of N-cyanomethylisoquinolinium chloride, isatins and ethyl cyanoacetate mainly resulted in functionalized spiro[indoline-3,8'-pyrido[2',3':4,5]pyrrolo[2,1-a]isoquinolines]...
January 20, 2017: Scientific Reports
Meha Fatima Aftab, Shabbir Khan Afridi, Uzma Rasool Mughal, Aneela Karim, Darakhshan Jabeen Haleem, Nurul Kabir, Khalid M Khan, Rahman M Hafizur, Rizwana S Waraich
Diabetes is associated with neurodegeneration. Glycation ensues in diabetes and glycated proteins cause insulin resistance in brain resulting in amyloid plaques and NFTs. Also glycation enhances gliosis by promoting neuroinflammation. Currently there is no therapy available to target neurodegenration in brain therefore, development of new therapy that offers neuroprotection is critical. The objective of this study was to evaluate mechanistic effect of isatin derivative URM-II-81, an anti-glycation agent for improvement of insulin action in brain and inhibition of neurodegenration...
January 16, 2017: Journal of Chemical Neuroanatomy
Zhi-Wen Zhou, Feng-Cheng Jia, Cheng Xu, Shi-Fen Jiang, Yan-Dong Wu, An-Xin Wu
An efficient transition-metal-free cascade reaction has been developed for the facile synthesis of 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-one derivatives from commercially available isatins and 2-haloaryl isothiocyanates. A preliminary mechanistic study suggested an interrupted Dimroth rearrangement was the key step for the successful transformation.
January 3, 2017: Chemical Communications: Chem Comm
Feng Zhang, Hongyan Zhang, Fang Wang
PURPOSE: A series of quinazoline isatine hybrid derivatives were designed and their molecular docking studies were performed to ascertain the inhibition of EGFR by these hybrids. METHODS: Molecular modelling and docking methods were employed to design and synthesize the molecules. The compounds which showed good binding properties were synthesized and characterized. After structural confirmation of these compounds they were evaluated for their antiproliferative activity on OVCAR-3 ovarian cancer cell line...
November 2016: Journal of B.U.ON.: Official Journal of the Balkan Union of Oncology
Ransheng Ding, Pegah R Bakhshi, Christian Wolf
An organocatalytic method that achieves insertion of isatins into aryl difluoronitromethyl ketones under mild conditions is described. The reaction occurs in the presence of 20 mol % of DBU and with 100% atom economy. A series of isatin derived difluoronitromethyl substituted tertiary alcohol benzoates and naphthoates were prepared in 81-99% yield. The general synthetic usefulness of these 3-hydroxyoxindole derivatives is demonstrated with the selective reduction to fluorooximes.
January 20, 2017: Journal of Organic Chemistry
O A Buneeva, O V Gnedenko, M V Medvedeva, A S Ivanov, A E Medvedev
The amyloid-beta peptide 1-42 formed during proteolytic processing of the amyloid precursor protein (APP) plays a key role in the development or progression of Alzheimer's disease (AD) and other pathologies associated with formation of protein aggregates in the central nervous system. Recent proteomic profiling of mouse and rat brain preparations by means of beta-amyloid peptide immobilized on Affigel-10 revealed a large group of amyloid-binding proteins (n>80). Many (about 25%) of these proteins were previously identified as isatin-binding proteins...
November 2016: Biomedit︠s︡inskai︠a︡ Khimii︠a︡
Alexander S Filatov, Nickolay A Knyazev, Alexander P Molchanov, Taras L Panikorovsky, Rafael R Kostikov, Anna G Larina, Vitali M Boitsov, Alexander V Stepakov
3-Spiro[cyclopropa[a]pyrrolizine]- and 3-spiro[3-azabicyclo[3.1.0]hexane]oxindoles were prepared in moderate to high yields via one-pot three-component reactions using substituted isatins, α-amino acids, and cyclopropenes. The key step is an intramolecular [3 + 2]-cycloaddition reaction of an in situ generated azomethine ylide onto a cyclopropene. Both N-substituted and N-unsubstituted α-amino acids, dipeptide Gly-Gly, and also benzylamine were used as the amine component for the azomethine ylide generation...
January 3, 2017: Journal of Organic Chemistry
Ryosuke Tanaka, Maki Yazawa, Yuri Morikawa, Hidenobu Tsutsui, Mamoru Ohkita, Tokihito Yukimura, Yasuo Matsumura
Ischaemic acute kidney injury (AKI) is a leading killer of both sexes; however, resistance to this injury is higher among women than men. We found that renal venous noradrenaline (NAd) overflow after reperfusion played important roles in the development of ischaemic AKI, and that the attenuation of AKI observed in female rats may be dependent on depressing the renal sympathetic nervous system with endogenous oestrogen. In the present study, we used male and female Sprague-Dawley rats to investigate whether sex differences in the pathogenesis of ischaemic AKI are related to the degradation of NAd by monoamine oxidase (MAO) in the kidney...
December 20, 2016: Clinical and Experimental Pharmacology & Physiology
Samar El-Kalyoubi, Fatimah Agili
A variety of different compounds of fused uracils were prepared simply by the heating of 6-hydrazinyl-1-methyl-, 6-hydrazinyl-1-propyl-, or 6-hydrazinyl-1,3-dipropyluracil under reflux with ninhydrin, isatin, benzylidene malononitrile, benzylylidene ethyl cyanoacetate, benzil, and phenacyl bromide derivatives. The newly synthesized compounds were completely screened for antimicrobial and antitumor activity.
December 14, 2016: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Keisuke Kobayashi, Taichi Ohshiro, Hiroshi Tomoda, Feng Yin, Hai-Lei Cui, Pandurang V Chouthaiwale, Fujie Tanaka
Synthesis of new functionalized molecules and identification of biofunctional molecules can lead to the development of therapeutic leads and molecular tools for biomedical research. We have recently reported oxa-hetero-Diels-Alder reactions of enones with isatins to provide functionalized spirooxindole tetrahydropyran derivatives. Twenty-one compounds from the spirooxindole tetrahydropyran derivatives and related molecules were screened for inhibition of sterol O-acyltransferase (SOAT) isozymes SOAT1 and SOAT2...
December 15, 2016: Bioorganic & Medicinal Chemistry Letters
Mayuri A Borad, Manoj N Bhoi, Sanjay K Rathwa, Mahesh S Vasava, Hitesh D Patel, Chirag N Patel, Himanshu A Pandya, Edwin A Pithawala, John J Georrge
In the current investigation, we prepared a series of novel spiro[indole-thiazolidines] derivatives (5a-5h) from 5-substituted isatin derivatives and thioglycolic acid (TGA) with ZrSiO2 as an efficient catalyst under microwave irradiation. The significant merits of this protocol have some significant merits such as simplicity in operation, simple, efficient workup, good practical yields of product and the employment of recyclable catalyst. All the new synthesized scaffold has been well characterized by various spectroscopic methods and elemental analysis...
November 11, 2016: Interdisciplinary Sciences, Computational Life Sciences
Jian-Qiang Zhao, Deng-Feng Yue, Xiao-Mei Zhang, Xiao-Ying Xu, Wei-Cheng Yuan
The asymmetric Neber reaction of 3-O-sulfonyl ketoxime, in situ generated from isatin ketoxime and sulfonyl chloride, for the synthesis of chiral spirocyclic oxindole compounds is reported. With the developed protocol, a range of chiral spirooxindole 2H-azirines could be obtained in good to excellent yields and up to a 92 : 8 enantiomeric ratio by using (DHQD)2PHAL as the catalyst. This methodology is the only example of the catalytic asymmetric construction of spirooxindole 2H-azirine compounds.
November 7, 2016: Organic & Biomolecular Chemistry
Claudia Melis, Rita Meleddu, Andrea Angeli, Simona Distinto, Giulia Bianco, Clemente Capasso, Filippo Cottiglia, Rossella Angius, Claudiu T Supuran, Elias Maccioni
The isatin scaffold is the constitutive fragment of several natural and synthetic bioactive molecules. Albeit several benzene sulphonamide-based carbonic anhydrase inhibitors (CAIs) have been reported, only recently isatin benzene sulphonamides have been studied and proposed as CAIs. In this study we have designed, synthesised, and evaluated the biological activity of a series of differently substituted isatin-based benzene sulphonamides which have been designed for the inhibition of carbonic anhydrase isoforms...
October 24, 2016: Journal of Enzyme Inhibition and Medicinal Chemistry
Nadia G Kandile, Mansoura I Mohamed, Hind M Ismaeel
New compounds based on oxindole moiety were synthesized via the reaction of 5-substitued isatins 1a-e with different nucleophiles such as benzidine, 3,3'-dimethoxybenzidine 2a,b and 2,6-diaminopyridine 3 to afford three different classes of bis-Schiff bases 4a-e, 5a-e and 6a-e, respectively. The structures of the new compounds were elucidated on the basis of their FTIR, (1)H NMR, (13)C NMR, GC/MS spectral data and elemental analysis. The in vitro antimicrobial activity of the new compounds was evaluated using a broth dilution technique in terms of minimal inhibitory concentration (MIC) against four bacterial and two fungal pathogens and anticancer activities against HELA cervix...
October 21, 2016: Journal of Enzyme Inhibition and Medicinal Chemistry
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