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Myron Triantafyllakis, Kalliopi Sfakianaki, Dimitris Kalaitzakis, Georgios Vassilikogiannakis
A straightforward synthesis of substituted 2-oxindoles, 3-hydroxy-2-oxindoles, and isatins has been developed. Easily accessible furans were transformed into tetrahydropyranopyrrolones by a singlet oxygen initiated cascade reaction sequence. An acid-catalyzed rearrangement, followed by aromatization, gave access to a variety of 2-oxindole motifs, which were oxidized to 3-hydroxy-2-oxindoles or isatins using methylene blue as a radical initiator and molecular oxygen as a terminal oxidant.
May 24, 2018: Organic Letters
Feng-Cheng Jia, Cheng Xu, Yu-Wei Wang, Zhi-Peng Chen, Yun-Feng Chen, An-Xin Wu
A copper-catalyzed cascade reaction using isatins and amidine hydrochlorides for the synthesis of 2-(1,3,5-triazin-2-yl)aniline derivatives has been developed. This reaction features commercially available starting materials, mild reaction conditions and good functional group tolerance.
May 23, 2018: Organic & Biomolecular Chemistry
Xiaoze Bao, Shiqiang Wei, Xingkai Qian, Jingping Qu, Baomin Wang, Liwei Zou, Guangbo Ge
A catalytic asymmetric [3 + 2] cyclization of novel 4-isothiocyanato pyrazolones and isatin-derived ketimines was developed, delivering a wide range of intriguing dispirotriheterocyclic products in high yield with excellent diastereoselectivity and enantioselectivity. A chiral sulfoxide derivative of this dispirocyclic product was identified to be a promising hit of the human carboxylesterase 1 inhibitor, and the significant difference of the activity between two enantiomers emphasized the importance of this asymmetric process...
May 22, 2018: Organic Letters
Anna Florinskaya, Pavel Ershov, Yuri Mezentsev, Leonid Kaluzhskiy, Evgeniy Yablokov, Alexei Medvedev, Alexis Ivanov
We have developed an original experimental approach based on the use of surface plasmon resonance (SPR) biosensors, applicable for investigation of potential partners involved in protein⁻protein interactions (PPI) as well as protein⁻peptide or protein⁻small molecule interactions. It is based on combining a SPR biosensor, size exclusion chromatography (SEC), mass spectrometric identification of proteins (LC-MS/MS) and direct molecular fishing employing principles of affinity chromatography for isolation of potential partner proteins from the total lysate of biological samples using immobilized target proteins (or small non-peptide compounds) as ligands...
May 18, 2018: Sensors
Guang-Jian Mei, Feng Shi
Chiral spirooxindoles are privileged heterocyclic motifs, which are widely found in natural alkaloids and pharmaceuticals. Moreover, the construction of chiral spiro-cyclic frameworks is a long-lasting challenge in organic synthesis. The past four years have witnessed significant developments in this field, and this feature article outlines the recent progress in the catalytic asymmetric synthesis of spirooxindoles, including the contributions of our group. The catalytic asymmetric construction of spirooxindoles has greatly benefited from the utilization of oxindole derivatives as starting materials, including isatin derivatives, methyleneindolinones, indolin-2-one derivatives and isatin-derived 3-indolylmethanols...
May 17, 2018: Chemical Communications: Chem Comm
Ana Paula Lopes de Melo, Leandro Bresolin, Bianca Barreto Martins, Vanessa Carratu Gervini, Adriano Bof de Oliveira
The reaction in methanol of CuII acetate monohydrate with 5-fluoro-isatin 3-oxime deprotonated with KOH in a 1:2 molar ratio and recrystallization from pyridine yielded the title compound, [Cu(C8 H4 FN2 O2 )2 (C5 H5 N)2 ]. In the centrosymmetric complex, the anionic form of the isatin oxime acts as a κ2 N , O donor, building five-membered metallarings. The CuII cation is sixfold coordinated in a slightly distorted octa-hedral environment by two trans , equatorial, anionic isatin derivatives and two trans pyridine ligands in axial positions...
April 1, 2018: Acta Crystallographica. Section E, Crystallographic Communications
Hou-Ze Gui, Yu-Ning Gao, Yin Wei, Min Shi
A catalyst-free self-catalyzed [3+2] cycloaddition reaction of isatin-derived α-(trifluoromethyl)imines with vinylpyridines is reported. The reaction offers a straightforward and atom-economical procedure for the preparation of a series of 5'-trifluoromethyl-spiro[pyrrolidin-3,2'-oxindoles] in excellent yields and diastereoselectivities. The reaction mechanism has been investigated by control experiments, DFT calculation of pKa values and the kinetic profiles, revealing that this reaction featured the mutual activation between isatin-derived α-(trifluoromethyl)imines and vinylpyridine to generate the reactive species...
May 13, 2018: Chemistry: a European Journal
Jian Cao, Weiwei An, Audrey G Reeves, Alexander R Lippert
Peroxynitrite (ONOO- ) is a highly reactive oxygen species which has been recognized as an endogenous mediator of physiological activities like the immune response as well as a damaging agent of oxidative stress under pathological conditions. While its biological importance is becoming clearer, many of the details of its production and mechanism of action remain elusive due to the lack of available selective and sensitive detection methods. Herein, we report the development, characterization, and biological applications of a reaction-based chemiluminescent probe for ONOO- detection, termed as PNCL ...
March 7, 2018: Chemical Science
A G Bharathi Dileepan, T Daniel Prakash, A Ganesh Kumar, P Shameela Rajam, V Violet Dhayabaran, R Rajaram
In the present work, five macrocyclic compounds, C18 H12 N2 O4 (1), C38 H24 N8 O6 (1a), C38 H24 N8 O4 S2 (1b), C40 H32 N8 O4 (2a) and C48 H32 N8 O4 (2b) have been synthesized and thoroughly characterized by elemental analysis, FT-IR, 1D & 2D NMR and electron spray ionization mass spectral analysis. The DNA binding ability of these compounds were investigated in vitro by UV-Visible, fluorescence, circular dichroism (CD) spectroscopy and viscosity measurements. The results indicate that these compounds possess strong DNA binding affinity via intercalation, while the order of binding strength followed the trend 2b (1...
April 21, 2018: Journal of Photochemistry and Photobiology. B, Biology
A V Florinskaya, P V Ershov, Y V Mezentsev, L A Kaluzhskiy, E O Yablokov, O A Buneeva, V G Zgoda, A E Medvedev, A S Ivanov
It becomes increasingly clear that most proteins of living systems exist as components of various protein complexes rather than individual molecules. The use of various proteomic techniques significantly extended our knowledge not only about functioning of individual complexes but also formed a basis for systemic analysis of protein-protein interactions. In this study gel-filtration chromatography accompanied by mass-spectrometry was used for the interactome analysis of human liver proteins. In six fractions (with average molecular masses of 45 kDa, 60 kDa, 85 kDa, 150 kDa, 250 kDa, and 440 kDa) 797 proteins were identified...
March 2018: Biomedit︠s︡inskai︠a︡ Khimii︠a︡
Hao Wu, Zhiguo Zhang, Qingfeng Liu, Tongxin Liu, Nana Ma, Guisheng Zhang
The reaction of o-aminoacetophenones and arylboronic acids catalyzed by copper(II) salts in the presence of pyridine under an O2 atmosphere provides a general and efficient one-pot preparation of biologically interesting acridones. This relay reaction comprises an intermolecular Suzuki cross-coupling, intramolecular oxidative C(sp3 )-H amination, and C(sp2 )-H activation with simultaneous rearrangement of the generated isatin intermediates. This strategy tolerates both electron-donating and -withdrawing functionalities to afford various acridones in good to excellent yields...
April 26, 2018: Organic Letters
Bin Cheng, Bing Zu, Yuntong Li, Cheng Tao, Chen Zhang, Renqi Wang, Yun Li, Hongbin Zhai
CF3-containing spiro-epoxyoxindoles were successfully prepared via the Corey-Chaykovsky reaction of N-alkyl isatins with the ylide generated from Ph2S+CH2CF3OTf- with almost exclusive diastereoselectivity. Further derivatizations of these spiro-epoxyoxindoles were explored via a photochemical reaction or Lewis acid-promoted allylation.
April 26, 2018: Organic & Biomolecular Chemistry
Paulo Andre Teixeira De Moraes Gomes, Lindomar Jose Pena, Ana Cristina Lima Leite
Arboviruses have been spreading rapidly throughout the Western Hemisphere in recent decades. Among the arboviruses with high morbidity and mortality are members of the Alphavirus and Flavivirus genera. Within the first genus, Chikungunya virus (CHIKV) is considered one of the most challenging human arboviral infections with global significance and without any specific antiviral agent. Flaviviruses are some of the most important causes of encephalitis, haemorrhagic disease, and developmental defects. Japanese encephalitis virus (JEV), West Nile virus (WNV), dengue virus (DENV) and Zika virus (ZIKV) are examples of flaviviruses without clinically approved antiviral agents...
April 23, 2018: Mini Reviews in Medicinal Chemistry
Xue Tang, Ying-Juan Gao, Hui-Qing Deng, Jin-Ju Lei, Si-Wei Liu, Lin Zhou, Yin Shi, Hao Liang, Jie Qiao, Li Guo, Bo Han, Hai-Lei Cui
We have developed a mild and scalable catalyst-free [3 + 2] cyclization of dihydroisoquinolines and isatin-derived Morita-Baylis-Hillman carbonates. The incorporation of tetrahydroisoquinoline and spirooxindole frameworks could be realized affording highly functionalized heterocycles in moderate to excellent yields with good diastereocontrols (up to 92% yields, >20 : 1 dr). The extension of this method to dihydro-β-carbolines has also been achieved. A gram-scale reaction could be performed successfully enabling the potential application for further biomedical research...
April 24, 2018: Organic & Biomolecular Chemistry
Andrei V Bogdanov, Ilyuza F Zaripova, Alexandra D Voloshina, Anastasia S Sapunova, Natalia V Kulik, Julia K Voronina, Vladimir F Mironov
A high-yield synthesis of some novel isatin-3-acylhydrazones on the base of 5-ethylisatin derivatives and Girard's reagent T is described. Antimicrobial activity preliminary SAR study of both 1-benzylated isatins and water-soluble hydrazones was established. The most active against Staphylococcus aureus and Bacillus cereus are ammonium salts bearing 3,4-dichloro- or 4-CF3 substituents in benzyl fragment. This article is protected by copyright. All rights reserved.
April 23, 2018: Chemistry & Biodiversity
Mathilde Jaglin, Moez Rhimi, Catherine Philippe, Nicolas Pons, Aurélia Bruneau, Bénédicte Goustard, Valérie Daugé, Emmanuelle Maguin, Laurent Naudon, Sylvie Rabot
Gut microbiota produces a wide and diverse array of metabolites that are an integral part of the host metabolome. The emergence of the gut microbiome-brain axis concept has prompted investigations on the role of gut microbiota dysbioses in the pathophysiology of brain diseases. Specifically, the search for microbe-related metabolomic signatures in human patients and animal models of psychiatric disorders has pointed out the importance of the microbial metabolism of aromatic amino acids. Here, we investigated the effect of indole on brain and behavior in rats...
2018: Frontiers in Neuroscience
Wenyan Gao, Luding Zhang, Xiaoqian Wang, Li Yu, Changhong Wang, Yang Gong
Indirubin and isatin have been used in the treatment of inflammatory diseases due to their anti-inflammatory properties. The present study aimed to evaluate the combined effect of indirubin and isatin on dextran sulfate sodium (DSS)-induced ulcerative colitis (UC). UC was induced by administration of 3% (w/v) DSS solution and then the model mice were administered indirubin (10 mg/kg) or/and isatin (10 mg/kg) by gavage once daily for a week. The results showed that indirubin or/and isatin significantly inhibited weight loss, lowered disease activity index (DAI), ameliorated pathological changes, decreased the levels of pro-inflammatory mediators and myeloperoxidase (MPO) activity, increased anti-inflammatory cytokine and Foxp3 expression, suppressed CD4+ T cell infiltration, and inhibited oxidative stress and epithelial cell apoptosis...
April 19, 2018: Biochemistry and Cell Biology, Biochimie et Biologie Cellulaire
Jasneet Kaur, Swapandeep Singh Chimni
3-Substituted-3-aminooxindoles have attracted the attention of organic chemists since they have a common core structural motif found in many natural products and biologically active compounds. During the past six years, the new synthetic methodologies for the synthesis of this moiety have shown rapid growth. Thus, an update of our previous review has become necessary and this review includes the literature on this topic, covering the reactions of isatin imine explored in various organic transformations catalyzed by metals and organocatalysts...
April 17, 2018: Organic & Biomolecular Chemistry
Xing Yang, Ze-Hun Cao, Yang Zhou, Feng Cheng, Zi-Wei Lin, Zhi Ou, Ye Yuan, Yi-Yong Huang
A three-component Petasis-type gem-difluoroallylation reaction of using pinacol gem-difluoroallylboronates, aldehydes or isatin, and β-amino alcohols enabled by the neighboring hydroxyl group in amine is reported, affording various racemic and chiral gem-difluorohomoallylamine derivatives with good to excellent results. Based on the control experiment and stereochemistry of the product, a proposed reaction pathway is illustrated to clarify the origin of regio- and stereoselectivity under protic solvent conditions...
April 13, 2018: Organic Letters
Sarra Ben Hamida, Sidra Iftekhar, Indu Ambat, Varsha Srivastava, Mika Sillanpää, Zahra Amri, Neji Ladhari
The study aims to identify the denim ozonation by-products under different operating conditions and investigate the chemical toxicity of these compounds via the inhibitory effect of the sample on the light emission of bioluminescent bacteria (Vibriofischeri) and on human health using the HepG2 human hepatoma cell line. Various by-products in treated denim extract were detected w gas chromatography-mass spectrometry (GC-MS) analysis. The results revealed that the main oxidation by-product was isatin (1H-indole-2,3-dione), which formed in excess amounts on wet ozonated denim...
April 4, 2018: Chemosphere
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