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Pavel Ershov, Yuri Mezentsev, Andrey Gilep, Sergey Usanov, Olga Buneeva, Alexei Medvedev, Alexis Ivanov
Isatin (indol-2,3-dione) is an endogenous non-peptide regulator exhibiting a wide range of biological and pharmacological activities, which are poorly characterized in terms of their molecular mechanisms. Identification of many isatin-binding proteins in the mammalian brain and liver suggests that isatin may influence their functions. We have hypothesized that besides direct action on particular protein targets, isatin can act as a regulator of protein-protein interactions (PPIs). In this SPR-based biosensor study we have found that physiologically relevant concentrations of isatin (25-100 μM) increase affinity of interactions between human recombinant ferrochelatase (FECH) and NADPH-dependent adrenodoxin reductase (ADR)...
September 14, 2017: Protein Science: a Publication of the Protein Society
Jiayong Zhang, Cheng Cheng, Dian Wang, Zhiwei Miao
A phosphine-catalyzed [3+2] annulation of isatin derived α,β-unsaturated ketones with alkynoates for the synthesis of cyclopentene spiro-oxindole skeletons has been developed. This reaction afforded the desired products in high to excellent yields (up to 99%) with high regioselectivity and moderate to high diastereoselectivities (up to 20:1). This strategy allows facile diastereoselective preparation of biologically important spiro-(cyclopentene) oxindoles containing three contiguous stereocenters, including the quaternary stereogenic center joining the two rings...
September 12, 2017: Journal of Organic Chemistry
O A Buneeva, A T Kopylov, L N Nerobkova, I G Kapitsa, V G Zgoda, A E Medvedev
Isatin (indole-2,3-dione) is an endogenous indole found in the mammalian brain, peripheral organs and body fluids. It acts as a neuroprotector, which decreases manifestation of locomotor impairments in animal models of Parkinson's disease. A wide range of biological activity of isatin is associated with interaction of this regulator with numerous isatin-binding proteins. The aim of this study was to investigate the profile of brain isatin-binding proteins in mice with MPTP-induced Parkinsonism (90 min and seven days after administration of this neurotoxin)...
July 2017: Biomedit︠s︡inskai︠a︡ Khimii︠a︡
Jiang Meng, Renmeng Jia, Jiaying Leng, Min Wen, Xingxin Yu, Wei-Ping Deng
A novel protocol for the synthesis of unsymmetrical indigo-like (E)-α-amino enaminones by rhodium-catalyzed transformations of isatins with 1-tosyl-1,2,3-triazoles has been developed. A plausible reaction mechanism is proposed to account for the formation of structurally important unsymmetrical indigo analogues, which represents a new strategy for C-C bond formation based on the transformations of secondary amides and rhodium azavinylcarbenes.
August 24, 2017: Organic Letters
Shengsheng Jiang, Kai Li, Jun Yan, Kuangxi Shi, Chengtao Zhao, Limin Yang, Guofu Zhong
Elimination/[3+2] cycloaddition reactions of simple enals and unprotected isatins with haloamides have been developed. This transformation provides rapid access to highly functionalized oxazolidin-4-ones that are represented in bioactive compounds.
August 31, 2017: Journal of Organic Chemistry
Zhansheng Wang, Hui Xu, Lirong Yan, Qingyang Li, Liangce Rong
An efficient and green reaction of isatins, 3-amino-1-phenyl-2-pyrazolin-5-one (3-amine-1H-pyrazole), and [Formula: see text]-diketone in aqueous medium in the presence of [Formula: see text]-[Formula: see text] is reported, and a series of novel spirocompounds was obtained with high yields. The advantages of this reaction were simple procedure, moderate reaction conditions, and wide range of substrates. More importantly, the catalyst [Formula: see text]-[Formula: see text] could be recovered for reuse up to five times...
August 21, 2017: Molecular Diversity
Honghe Ji, Yingzu Zhu, Yu Shao, Jing Liu, Yu Yuan, Xiaodong Jia
In the presence of catalytic triarylamine radical cation, an sp(3)-sp(2) consecutive C-H functionalization of N-arylglycine amides was achieved, providing a series of isatin derivatives in high yields. In this transformation, the initial aerobic oxidation of the relatively active sp(3) C-H bonds triggered the following intramolecular cyclization, in which the aniline group was employed as a removable auxiliary group to enable the consecutive process.
August 30, 2017: Journal of Organic Chemistry
Prakash R Mali, Prashishkumar K Shirsat, Navnath Khomane, Lakshama Nayak, Jagadeesh Babu Nanubolu, H M Meshram
The multicomponent reaction between isatin, amino acid, but-2-ynedioates, and phenacyl bromide has been developed using microwave irradiation under catalyst and base-free conditions in aqueous medium. This synthetic protocol is useful for the synthesis of various functionalized spirooxindole derivatives. This MCR exhibits a broad substrate scope with excellent yields and shorter reaction time. Additionally the synthesized spirooxindole derivatives were evaluated for their anticancer activity against three human cancer cell lines: MCF-7 (breast), A549 (lung), and HeLa cervical...
September 7, 2017: ACS Combinatorial Science
Harbinder Singh, Jatinder V Singh, Manish K Gupta, Ajit K Saxena, Sahil Sharma, Kunal Nepali, Preet Mohinder S Bedi
In an attempt to develop potent anti-tubulin agents against most dreadful disease cancer, a library of 28 novel triazole tethered isatin-coumarin hybrids were synthesized by click chemistry approach. Synthesized hybrids were characterized and evaluated against a panel of human cancer cell lines viz. THP-1, COLO-205, HCT-116 and PC-3. Biological assay unveiled that, compounds A-1 to A-6, B-1 to B-4 and C-1 to C-3 displayed significant inhibitory potential against THP-1, COLO-205 and HCT-116 cell lines which were more sensitive towards the designed hybrids...
September 1, 2017: Bioorganic & Medicinal Chemistry Letters
Chunfeng Chen, Chunlei Lv, Jianfeng Liang, Jianqing Jin, Lijun Wang, Chunlei Wu, Runpu Shen
A simple and efficient method for the synthesis of spiro[indoline-3,9'-xanthene]trione derivatives by means of condensation between isatins and 1,3-cyclohexanedione in the presence of a catalytic amount of magnesium perchlorate at 80 °C in 50% aqueous ethanol medium has been described. Notably, the present method offers desirable advantages of good yields, simplicity of workup procedure, easy purification, and reduced reaction times.
August 4, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Fatima Iftikhar, Yousaf Ali, Farooq Ahmad Kiani, Syed Fahad Hassan, Tabeer Fatima, Ajmal Khan, Basit Niaz, Abbas Hassan, Farzana Latif Ansari, Umer Rashid
In our previous report, we have identified 3,4-dihydropyrimidine scaffold as promising class of urease inhibitor in a structure based virtual screen (SBVS) experiment. In present study, we attempted to optimize the scaffold by varying C-5 substituent. The elongation of the C-5 chain was achieved by the reaction of C-5 ester with hydrazine leading to C-5 carbohydrazides which were further used as building blocks for the synthesis of fifteen new compounds having diverse moieties. A significantly higher in vitro urease inhibitory activity with IC50 values in submicromolar range was observed for semithiocarbazide derivatives (4a-c, 0...
July 19, 2017: Bioorganic Chemistry
Mohamed I Attia, Wagdy M Eldehna, Samar A Afifi, Adam B Keeton, Gary A Piazza, Hatem A Abdel-Aziz
The synthesis and molecular characterization of new isatin-based hydrazonoindolin-2-ones 4a-o and 7a-e are reported. The in vitro anti-proliferative potential of the synthesized compounds 4a-o and 7a-e was examined against HT-29 (colon), ZR-75 (breast) and A549 (lung) human cancer cell lines. Compounds 7b, 7d and 7e were the most active congeners against the tested human cancer cell lines with average IC50 values of 4.77, 3.39 and 2.37 μM, respectively, as compared with the reference isatin-based drug, sunitinib, which exhibited an average IC50 value of 8...
2017: PloS One
Manoela Viar Fogaça, Priscila de Matos Cândido-Bacani, Lucas Milanez Benicio, Lara Martinelli Zapata, Priscilla de Freitas Cardoso, Marcelo Tempesta de Oliveira, Tamara Regina Calvo, Eliana Aparecida Varanda, Wagner Vilegas, Ilce Mara de Syllos Cólus
CONTEXT: Indigofera suffruticosa Miller (Fabaceae) and I. truxillensis Kunth produce compounds, such as isatin (ISA) and indirubin (IRN), which possess antitumour properties. Their effects in mammalian cells are still not very well understood. OBJECTIVE: We evaluated the activities of ISA and/or IRN on cell viability and apoptosis in vitro, their genotoxic potentials in vitro and in vivo, and the IRN- and ISA-induced expression of ERCC1 or BAX genes. MATERIALS AND METHODS: HeLa and/or CHO-K1 cell lines were tested (3 or 24 h) in the MTT, Trypan blue exclusion, acridine orange/ethidium bromide, cytokinesis-blocked micronucleus (CBMN) and comet (36, 24 and 72 h) tests after treatment with IRN (0...
December 2017: Pharmaceutical Biology
Kinthada Ramakumar, Tapan Maji, James J Partridge, Jon A Tunge
A new method is developed for the synthesis of spirooxindoles from amines and isatins via C-H functionalization. The reaction leverages the tert-amino effect to form an enolate-iminium intermediate via [1,5]-hydride shift followed by cyclization. Interestingly the hydride migrates to the N atom of a C═N, which is atypical for hydride additions to imines.
July 24, 2017: Organic Letters
Zhi Xu, Shu Zhang, Xufeng Song, Min Qiang, Zaosheng Lv
A set of novel gatifloxacin-1H-1,2,3-triazole-isatin hybrids 6a-l was designed, synthesized and evaluated for their in vitro anti-mycobacterial activities against M. tuberculosis (MTB) H37Rv and MDR-TB as well as cytotoxicity. The results showed that all the targets (MIC: 0.025-3.12μg/mL) exhibited excellent inhibitory activity against MTB H37Rv and MDR-TB, but were much more toxic (CC50: 7.8-62.5μg/mL) than the parent gatifloxacin (GTFX) (CC50: 125μg/mL). Among them, 61 (MIC: 0.025μg/mL) was 2-32 times more potent in vitro than the references INH (MIC: 0...
July 8, 2017: Bioorganic & Medicinal Chemistry Letters
Adel S El-Azab, Abdullah Al-Dhfyan, Alaa A-M Abdel-Aziz, Laila A Abou-Zeid, Hamad M Alkahtani, Abdulrahman M Al-Obaid, Manal A Al-Gendy
A new series of quinazolinone compounds 16-34 incorporating isatin moieties was synthesized. The antitumor efficacy of the compounds against MDA-MB-231, a breast cancer cell line, and LOVO, a colon cancer cell line, was assessed. Compounds 20, 21, 22, 23, 25, 27, 28, 29, 30, 31, 32, 33, and 34 displayed potent antitumor activity against MDA-MB-231 and LOVO cells (IC50: 10.38-38.67 μM and 9.91-15.77 μM, respectively); the comparative IC50 values for 5-fluorouracil and erlotinib in these cells lines were 70...
December 2017: Journal of Enzyme Inhibition and Medicinal Chemistry
Magda F Mohamed, Amr Mohamed Abdelmoniem, Ahmed H M Elwahy, Ismail A Abdelhamid
An efficient one pot synthesis of bis spiro-cyclic 2-oxindole derivatives of pyrimido[4,5-b]quinoline-4,6-dione using 6-aminouracil, bis-isatin and dimedone has been developed. The cytotoxic effect against different human cell lines MCF7, HCT116 and A549 cell lines was evaluated. The derivative 6a, was found the most encouraging compound in this series and it was selected for molecular studies against MCF7. Our data indicated that compound 6a is an attractive target for breast cancer, as it inhibits proliferation, cell cycle progression and induces apoptosis of tumor cells...
June 30, 2017: Current Cancer Drug Targets
Zhi Xu, Xu-Feng Song, Yuan-Qiang Hu, Min Qiang, Zao-Sheng Lv
Twelve novel 1H-1,2,3-triazole-tethered gatifloxacin (GTFX) isatin conjugates 5a-l with greater lipophilicity compared with GTFX were designed, synthesized and evaluated for their in vitro anti-mycobacterial activities against M. tuberculosis (MTB) H37Rv and MDR-TB as well as cytotoxicity. The preliminary results showed that all the targets (MIC: 0.10-8 μg/mL) exhibited excellent inhibitory activity against MTB H37Rv and MDR-TB, but eight of them (CC50: 7.8-62.5 μg/mL) were much more toxic than the parent GTFX (CC50: 125 μg/mL)...
June 9, 2017: European Journal of Medicinal Chemistry
Bing Wang, Qing Lu, Qi Fang, Ting-Ting Zhang, Ying-Ying Jin
In the title compound, C14H8ClNO2, the dihedral angle between the isatin moiety (r.m.s. deviation = 0.014 Å) and the phenyl ring is 51.8 (1)°. All mol-ecules have the same 'frozen chiral' conformation in the non-centrosymmetric P212121 space group. A polycrystalline sample of the title compound exhibits a considerable second-order non-linear optical effect (frequency doubling of 1064 nm light to output 532 nm light). In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, generating chains along the [100] direction...
June 1, 2017: Acta Crystallographica. Section E, Crystallographic Communications
Wen-Ting Wei, Wen-Ming Zhu, Wei-Wei Ying, Yi Wu, Yi-Ling Huang, Hongze Liang
A metal-free method for the synthesis of isatin oximes was developed through the radical coupling reactions of oxindoles with t-BuONO. This protocol provides a practical and environmentally benign method for the construction of C-N bonds in water at room temperature without using any other reagents. The advantages of this strategy are its mild reaction conditions and clean procedure.
June 27, 2017: Organic & Biomolecular Chemistry
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