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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 9, 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
Rita Meleddu, Simona Distinto, Angela Corona, Enzo Tramontano, Giulia Bianco, Claudia Melis, Filippo Cottiglia, Elias Maccioni
A series of 3-3-{2-[2-3-methyl-4-phenyl-2,3-dihydro-1,3-thiazol-2-ylidene]hydrazin-1-ylidene-2,3-dihydro-1H-indol-2-one derivatives has been designed and synthesized to study their activity on both HIV-1 (Human Immunodeficiency Virus type 1) RT (Reverse Transcriptase) associated functions. These derivatives are analogs of previously reported series whose biological activity and mode of action have been investigated. In this work we investigated the influence of the introduction of a methyl group in the position 3 of the dihydrothiazole ring and of a chlorine atom in the position 5 of the isatin nucleus...
October 21, 2016: Journal of Enzyme Inhibition and Medicinal Chemistry
Nagaraju Molleti, Jun Yong Kang
A highly efficient phospha-aldol reaction for the synthesis of α(1)-oxindole-α-hydroxyphosphonates is developed utilizing N-heterocyclic phosphine (NHP)-thiourea as a phosphonylation reagent under catalyst, additive free conditions. This methodology encompasses a variety of isatin derivatives to provide α(1)-oxindole- α-hydroxyphosphonates up to 99% yield.
September 26, 2016: Organic & Biomolecular Chemistry
Yunsheng Xue, Yuhui Wang, Zhongyan Cao, Jian Zhou, Zhao-Xu Chen
Density functional theory (DFT) calculations were performed to elucidate the mechanism and the origin of the high enantioselectivity of the aza-Henry reaction of isatin-derived N-Boc ketimine catalyzed by a quinine-derived catalyst (QN). The C-C bond formation step is found to be both the rate-determining and the stereo-controlled step. The results revealed the important role of the phenolic OH group in pre-organizing the complex of nitromethane and QN and stabilizing the in situ-generated nitronate and protonated QN...
October 12, 2016: Organic & Biomolecular Chemistry
Juanjuan Wang, Danfeng Huang, Ke-Hu Wang, Xiansha Peng, Yingpeng Su, Yulai Hu, Ying Fu
A convenient and efficient method for the constructions of 3-spirooxindole derivatives or 3,3'-disubstituted oxindoles has been developed from one-pot reactions of isatins, hydrazides or aromatic amines, 2-(bromomethyl)acrylic ester and tin powder in the presence of a catalytic amount of Brønsted or Lewis acid. The method avoids the use of toxic stannanes and allows easy operation. It is also proved that hydrazides are more favorable for intramolecular cyclization than amines.
October 12, 2016: Organic & Biomolecular Chemistry
James T Fleming, Corinne Wills, Paul G Waddell, Ross W Harrington, Lee J Higham
Six chiral MOP-phosphonites have been synthesised and compared via experimental and computational methods in an effort to quantify their differing structural and electronic profiles. They were found to be electron-poor ligands in comparison to their arylphosphine analogues and have a larger trans influence in square planar Pt(ii) complexes. Four [Rh(L(P))(η(2):η(2)-cod)Cl] complexes were synthesised and characterised by NMR, HRMS and X-ray crystallography. Two [Rh(L(P))2]BF4 complexes were prepared where one ligand acts as a chelating P,C-π-donor; detailed NMR studies demonstrated a hemilabile η(6)-coordination mode, which in one case was confirmed by X-ray crystallography...
October 4, 2016: Dalton Transactions: An International Journal of Inorganic Chemistry
Andrea Nitti, Marco Signorile, Massimo Boiocchi, Gabriele Bianchi, Riccardo Po, Dario Pasini
We report on the design, synthesis, and properties of innovative, planar, π-conjugated compounds in which a thiophene ring is fused with the skeleton of the naturally occurring dye isatin. The synthesis is achieved in high yields making use of an intramolecular direct arylation reaction as the key step, making the overall process potentially scalable. The synthetic sequence has been demonstrated also for an isatin bearing fluorine substituents on the aromatic ring. NMR and X-ray studies demonstrate the crosstalk occurring between the fused, coplanar, and conjugated moieties, making these novel dyes with a donor-acceptor character...
November 18, 2016: Journal of Organic Chemistry
Jianfeng Xu, Shiru Yuan, Maozhong Miao, Zhengkai Chen
A 1-hydroxybenzotriazole-assisted, N-heterocyclic carbene catalyzed direct β-functionalization of saturated carboxylic esters is disclosed. This formal [3 + 2] annulation reaction of carboxylic esters with isatins affords optically pure spirooxindole lactones (on gram scale) bearing two vicinal stereogenic centers. A dual role of HOBt is proposed based on controlled experiments to rationalize the enhancement of diastereoselectivity and enantioselectivity.
November 18, 2016: Journal of Organic Chemistry
Dinesh Kumar, Sandeep R Vemula, Narayanaganesh Balasubramanian, Gregory R Cook
Stereoselective indium-mediated organic reactions have enjoyed tremendous growth in the last 25 years. This is in part due to the insensitivity of allylindium to moisture, affording facile and practical reaction conditions coupled with outstanding functional group tolerance and minimal side reactions. Despite the plethora of articles about allylindium, there is much yet to be discovered and exploited for efficient and sustainable synthesis. In this Account, we describe indium-mediated synthetic methods for the preparation of chiral amines with the aim to present a balance of practical method development, novel asymmetric chemistry, and mechanistic understanding that impact multiple chemical and materials science disciplines...
October 4, 2016: Accounts of Chemical Research
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