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https://www.readbyqxmd.com/read/28720502/design-synthesis-and-in-vitro-anti-mycobacterial-evaluation-of-gatifloxacin-1h-1-2-3-triazole-isatin-hybrids
#1
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
https://www.readbyqxmd.com/read/28718672/synthesis-anticancer-and-apoptosis-inducing-activities-of-quinazoline-isatin-conjugates-epidermal-growth-factor-receptor-tyrosine-kinase-assay-and-molecular-docking-studies
#2
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
https://www.readbyqxmd.com/read/28669339/dna-fragmentation-cell-cycle-arrest-and-docking-study-of-novel-bis-spiro-cyclic-2-oxindole-of-pyrimido-4-5-b-quinoline-4-6-dione-derivatives-against-breast-carcinoma
#3
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
https://www.readbyqxmd.com/read/28646656/azide-alkyne-cycloaddition-towards-1h-1-2-3-triazole-tethered-gatifloxacin-and-isatin-conjugates-design-synthesis-and-in%C3%A2-vitro-anti-mycobacterial-evaluation
#4
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
https://www.readbyqxmd.com/read/28638657/6-chloro-1-phenyl-indoline-2-3-dione-absolute-structure-non-linear-optical-and-charge-transport-properties
#5
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
https://www.readbyqxmd.com/read/28604908/metal-free-synthesis-of-isatin-oximes-via-radical-coupling-reactions-of-oxindoles-with-t-buono-in-water
#6
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
https://www.readbyqxmd.com/read/28604855/metal-free-formal-carbon-halogen-bond-insertion-facile-syntheses-of-3-halo-3-3-disubstituted-oxindoles-and-spirooxindole-%C3%AE-butyrolactones
#7
Rong Zhou, Rongfang Liu, Kai Zhang, Ling Han, Honghui Zhang, Wenchao Gao, Ruifeng Li
A novel P(NMe2)3-mediated formal carbon-halogen bond insertion of isatins into allylic and benzylic bromides/chlorides has been realized, leading to a facile synthesis of 3-halo 3,3'-disubstituted oxindoles. This reaction relies on the unique dual nucleophilic-electrophilic reactivity pattern of the Kukhtin-Ramirez adduct via a cascade SN2-SN2 process. It also represents a rare metal-free approach for carbon-halogen bond insertion. Upon treatment with trifluoroacetic acid, spirooxindole-γ-butyrolactones have been efficiently prepared from the corresponding insertion products...
June 22, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28571319/isatin-n-n-cyclic-azomethine-imine-1-3-dipole-and-base-catalyzed-michael-addition-with-%C3%AE-nitrostyrene-via-c3-umpolung-of-oxindole
#8
Xiao Wang, Lin Wu, Peng Yang, Xiang-Jia Song, Hong-Xia Ren, Lin Peng, Li-Xin Wang
A new isatin N,N'-cyclic azomethine imine 1,3-dipole was devised, and an unusual Michael addition with β-nitrostyrene catalyzed by tributylamine under mild conditions has been developed. The new reaction featured the C3 umpolung of oxindole and an unusual formation of double bond. Notably, this new synthon performed as a donor rather than an acceptor. This protocol provided a promising method for the preparation of various 3-aminooxindoles with good yields in moderate diastereoselectivities.
June 1, 2017: Organic Letters
https://www.readbyqxmd.com/read/28568965/switchable-access-to-different-spirocyclopentane-oxindoles-by-n-heterocyclic-carbene-catalyzed-reactions-of-isatin-derived-enals-and-n-sulfonyl-ketimines
#9
Lei Wang, Sun Li, Marcus Blümel, Rakesh Puttreddy, Anssi Peuronen, Kari Rissanen, Dieter Enders
A novel NHC-catalyzed annulation protocol for the asymmetric synthesis of biologically important β-lactam fused spirocyclopentane oxindoles with four contiguous stereocenters, including two quaternary carbon centers, was developed. Alternatively, spirocyclopentane oxindoles containing an enaminone moiety can be achieved using the same starting materials, isatin-derived enals, and N-sulfonyl ketimines, in the presence of a slightly different NHC catalytic system. This switchable annulation strategy enables the selective assembly of both heterocyclic scaffolds with good yields and excellent enantioselectivities for a broad range of substrates...
June 1, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28551996/asymmetric-construction-of-3-3-disubstituted-oxindoles-bearing-vicinal-quaternary-tertiary-carbon-stereocenters-catalyzed-by-a-chiral-at-rhodium-complex
#10
Huihua Lin, Zijun Zhou, Jun Cai, Bowen Han, Lei Gong, Eric Meggers
A highly diastereo- and enantioselective synthesis of 3,3-disubstituted oxindoles bearing vicinal quaternary-tertiary carbon centers is enabled by a chiral-at-rhodium Lewis acid catalyst starting from isatin N-protected ketimines and 2-acyl imidazoles. The excellent results with 93-99% yields, diastereoselectivities of 43:1 to >200:1, and high enantioselectivities of 98.4 to >99% confirm the potential of bis-cyclometalated rhodium catalysts for the development of effective asymmetric transformations.
June 6, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28544113/the-role-of-water-in-catalyst-free-aldol-reaction-of-water-insoluble-n-methyl-2-4-thiazolidinedione-with-n-methyl-isatin-from-qm-mm-monte-carlo-simulation
#11
Jianming Zhao, Fen He, Fan Zhang, Xin Yang, Zhiyue Tian, Ying Xue
The role of water in the uncatalyzed aldol reaction of N-methyl-2,4-thiazolidinedione with N-methyl-isatin has been investigated using Monte Carlo statistical mechanics simulations utilizing the free-energy perturbation theory and the QM/MM model with PDDG/PM3 for the QM method under the "on water" and dimethyl sulfoxide (DMSO) environments. There are several conceivable orientations between thiazolidinedione and isatin in the process of C-C bond formation. However, the formation of C-C bond takes place between the re face of isatin and the si face of E-enol of the thiazolidinedione to form the preferred anti-type product, which results from enhancing hydrogen bonding interaction between water molecules and the oxygen atoms undergoing bond broken and bond formation during the reaction...
May 23, 2017: Chemphyschem: a European Journal of Chemical Physics and Physical Chemistry
https://www.readbyqxmd.com/read/28541051/catalytic-asymmetric-construction-of-the-tryptanthrin-skeleton-via-an-enantioselective-decarboxylative-4-2-cyclization
#12
Guang-Jian Mei, Chen-Yu Bian, Guo-Hao Li, Shao-Li Xu, Wen-Qin Zheng, Feng Shi
The first catalytic asymmetric construction of the tryptanthrin skeleton has been established, taking advantage of a palladium(0)/chiral ligand-catalyzed enantioselective decarboxylative [4 + 2] cyclization of vinyl benzoxazinanones with isatins. This reaction has not only provided a direct and efficient method for constructing chiral tryptanthrin skeleta in high yields and excellent enantioselectivities (up to 97% yield, >99% ee) but also represents the first catalytic asymmetric decarboxylative cyclization of vinyl benzoxazinanones with isatins...
May 25, 2017: Organic Letters
https://www.readbyqxmd.com/read/28537296/diastereo-and-enantioselective-construction-of-spirooxindole-scaffolds-through-a-catalytic-asymmetric-3-3-cycloaddition
#13
Can Li, Han Lu, Xiao-Xue Sun, Guang-Jian Mei, Feng Shi
A chiral phosphoric acid-catalyzed asymmetric [3 + 3] cycloaddition of C3-substituted 2-indolylmethanols with isatin-derived azomethine ylides has been established, which afforded chiral spirooxindoles in considerable yields, moderate to good enantioselectivities and excellent diastereoselectivities (up to 85% yield, 96 : 4 er, all >95 : 5 dr).
June 7, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28535683/electrocatalytic-c-h-n-h-coupling-of-2-aminoacetophenones-for-the-synthesis-of-isatins
#14
Peng Qian, Ji-Hu Su, Yukang Wang, Meixiang Bi, Zhenggen Zha, Zhiyong Wang
2'-Aminoacetophenones undergo a C(sp(3))-H oxidation followed by intramolecular C-N bond formation by virtue of a simple electrochemical oxidation in the presence of n-Bu4NI, providing various isatins with moderate to good yields. The reaction intermediates were detected, and a radical-based pathway was proposed.
June 2, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28529780/hirshfeld-analysis-and-mol-ecular-docking-with-the-rdr-enzyme-of-2-5-chloro-2-oxoindolin-3-yl-idene-n-methyl-hydrazinecarbo-thio-amide
#15
Jecika Maciel Velasques, Vanessa Carratu Gervini, Lisliane Kickofel, Renan Lira de Farias, Adriano Bof de Oliveira
The acetic acid-catalyzed reaction between 5-chloro-isatin and 4-methyl-thio-semicarbazide yields the title compound, C10H9ClN4OS (I) (common name: 5-chloro-isatin-4-methyl-thio-semicarbazone). The mol-ecule is nearly planar (r.m.s. deviation = 0.047 Å for all non-H atoms), with a maximum deviation of 0.089 (1) Å for the O atom. An S(6) ring motif formed by an intra-molecular N-H⋯O hydrogen bond is observed. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains propagating along the a-axis direction...
May 1, 2017: Acta Crystallographica. Section E, Crystallographic Communications
https://www.readbyqxmd.com/read/28513660/access-to-dihydropyridinones-and-spirooxindoles-application-of-n-heterocyclic-carbene-catalyzed-3-3-annulation-of-enals-and-oxindole-derived-enals-with-2-aminoacrylates
#16
Liang-Liang Zhao, Xing-Shuo Li, Li-Li Cao, Rui Zhang, Xiao-Qian Shi, Jing Qi
A strategy for the NHC-catalyzed synthesis of dihydropyridinones and spirooxindoles has been developed via [3+3] annulation reactions of enals or isatin-derived enals with 2-aminoacrylates under oxidative conditions. In this efficient strategy, the 2-aminoacrylates served as nucleophiles. Modifying the standard base switched the carbon-carbon double bond formation from 5,6-positions to 3,4-positions to generate 5,6-dihydropyridinones and 3,4-dihydropyridinones, respectively. Meanwhile, a diverse set of spirooxindole derivatives were also synthesized in good to excellent yields...
May 17, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28511906/design-synthesis-and-anti-tumor-activity-study-of-novel-histone-deacetylase-inhibitors-containing-isatin-based-caps-and-o-phenylenediamine-based-zinc-binding-groups
#17
Shuai Gao, Jie Zang, Qianwen Gao, Xuewu Liang, Qinge Ding, Xiaoyang Li, Wenfang Xu, C James Chou, Yingjie Zhang
As a hot topic of epigenetic studies, histone deacetylases (HDACs) are related to lots of diseases, especially cancer. Further researches indicated that different HDAC isoforms played various roles in a wide range of tumor types. Herein a novel series of HDAC inhibitors with isatin-based caps and o-phenylenediamine-based zinc binding groups have been designed and synthesized through scaffold hopping strategy. Among these compounds, the most potent compound 9n exhibited similar if not better HDAC inhibition and antiproliferative activities against multiple tumor cell lines compared with the positive control entinostat (MS-275)...
March 19, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28506067/pph3-mediated-reductive-annulation-reaction-between-isatins-and-electron-deficient-dienes-to-construct-spirooxindole-compounds
#18
Lei Zhang, Hong Lu, Guo-Qiang Xu, Zhu-Yin Wang, Peng-Fei Xu
A PPh3 mediated reductive annulation reaction between isatins and 4,4-dicyano-2-methylenebut-3-enoates was developed. The reaction provided an alternative method for constructing five- and three-membered all-carbon spirooxindole compounds. Lithium chloride as a Lewis acid played a key role in the synthesis of spirocyclopentenyl oxindole compounds.
May 19, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28487071/diversity-oriented-sustainable-synthesis-of-antimicrobial-spiropyrrolidine-thiapyrrolizidine-oxindole-derivatives-new-ligands-for-a-metallo-%C3%AE-lactamase-from-klebsiella-pneumonia
#19
Anshu Dandia, Shahnawaz Khan, Pragya Soni, Aayushi Indora, Dinesh Kumar Mahawar, Prateek Pandya, Chetan Singh Chauhan
A simple, environmentally benign and highly proficient microwave assisted one-pot approach for the synthesis of antimicrobial spiropyrrolidine/thiapyrrolizidine oxindole derivatives is reported assembling two pharmacophoric moieties (1,3-indanedione and pyrrolidine/thiapyrrolizidine) in a single molecular framework via three-component 1,3-dipolar cycloaddition reaction of substituted isatin, sarcosine/1,3-thiazoles-4-carboxylic acid and Knoevenagel adduct (2-Cyano-3-phenyl-acrylic acid ethyl ester or 2-Benzylidene-malononitrile) in 2,2,2-trifluoroethanol as a reusable green solvent...
April 27, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28481239/anti-inflammatory-activity-and-structure-activity-relationships-of-brominated-indoles-from-a-marine-mollusc
#20
Tarek B Ahmad, David Rudd, Joshua Smith, Michael Kotiw, Peter Mouatt, Lisa M Seymour, Lei Liu, Kirsten Benkendorff
Marine molluscs are rich in biologically active natural products that provide new potential sources of anti-inflammatory agents. Here we used bioassay guided fractionation of extracts from the muricid Dicathais orbita to identify brominated indoles with anti-inflammatory activity, based on the inhibition of nitric oxide (NO) and tumour necrosis factor α (TNFα) in lipopolysaccharide (LPS) stimulated RAW264.7 macrophages and prostaglandin E2 (PGE2) in calcium ionophore-stimulated 3T3 ccl-92 fibroblasts. Muricid brominated indoles were then compared to a range of synthetic indoles to determine structure-activity relationships...
May 6, 2017: Marine Drugs
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