- Synthesis and antibacterial activity of 1,5-disubstituted indolin-2-one derivatives containing sulfonamides
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A series of novel 1,5-disubstituted indolin-2-one derivatives containing sulfonamides as potential antibacterial agent were synthesized and the antibacterial activity was preliminary evaluated against two Gram-positive bacteria S. aureus ATCC26112, S. aureus SC and Gram-negative bacteria P. vulgaris in vitro. The results indicated that most of the target compounds exhibited promising antibacterial potency. Compounds 7b, 7d and 8b showed notable antimicrobial activity with corresponding inhibition zone (IZ = 19 mm, 21 mm and 23.5 mm, respectively) at the concentration of 100 μg/mL against S. aureus ATCC26112.
- Liang, Qiu-Xian,Liao, Ling,Luo, Juan,Pu, Shuai,Wang, Yu-Liang,Chen, Tian
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- Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold
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Carbonic anhydrase IX is a promising target for the search for new antitumor compounds with improved properties. Using the molecular hybridization approach, on the basis of structures of a selective carbonic anhydrase IX inhibitor 3 and an activator of apoptosis 2 (1), a series of 1-substituted isatin-5-sulfonamides 5a–5u were designed and synthesized. The study of the inhibitory activity of isatin-5-sulfonamides showed the ability to inhibit I, II, IX, XII isoforms at nano- and micromolar concentrations. Docking of compounds 5e and 5k into the active site of II and IX carbonic anhydrase isoforms showed the coordination of sulfonamidate anions with zinc cations, as well as a number of additional hydrophobic interactions. The trifluoromethylthio derivative 5r suppressed the growth of tumor cells at low micromolar concentrations, maintaining activity on resistant lines and under hypoxic conditions. Immunoblotting of MCF7 cells treated with the 5r revealed its antiestrogenic activity and ability to activate apoptosis in tumor cells.
- Krymov, Stepan K.,Scherbakov, Alexander M.,Salnikova, Diana I.,Sorokin, Danila V.,Dezhenkova, Lyubov G.,Ivanov, Ivan V.,Vullo, Daniela,De Luca, Viviana,Capasso, Clemente,Supuran, Claudiu T.,Shchekotikhin, Andrey E.
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- Efficient synthesis, biological evaluation, and docking study of isatin based derivatives as caspase inhibitors
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ABTRACT: In this paper, a new series of isatin-sulphonamide based derivatives were designed, synthesised and evaluated as caspase inhibitors. The compounds containing 1-(pyrrolidinyl)sulphonyl and 2-(phenoxymethyl)pyrrolidin-1-yl)sulphonyl substitution at C5 position of isatin core exhibited better results compared to unsubstituted derivatives. According to the results of caspase inhibitory activity, compound 20d showed moderate inhibitory activity against caspase-3 and ?7 in?vitro compared to Ac-DEVD-CHO (IC50 = 0.016 ± 0.002 μM). Among the studied compounds, some active inhibitors with IC50s in the range of 2.33–116.91 μM were identified. The activity of compound 20d was rationalised by the molecular modelling studies exhibiting the additional van der Waals interaction of N-phenylacetamide substitution along with efficacious T-shaped π-π and pi-cation interactions. The introduction of compound 20d with good caspase inhibitory activity will help researchers to find more potent agents.
- Firoozpour, Loghman,Gao, Lixin,Moghimi, Setareh,Pasalar, Parvin,Davoodi, Jamshid,Wang, Ming-Wei,Rezaei, Zahra,Dadgar, Armin,Yahyavi, Hoda,Amanlou, Massoud,Foroumadi, Alireza
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p. 1674 - 1684
(2020/09/02)
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- Isatin-5-sulfonamide derivative thereof in the preparation of a medicament for the treatment of atypical pneumonia application
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The invention relates to a novel isatin-5-sulfonamide derivative as represented by formula I. The formula I is described in the specification; in the formula, R1 is selected from the group consisting of C1-C6 alkyl groups, an aromatic methyl group and a heterocyclic aromatic methyl group, and R2 is a nitrogen-containing heterocyclic group. The invention further relates to a synthetic method for the derivative represented by the formula I and application of the derivative in preparation of medicines used for treating infective atypical pneumonia.
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Paragraph 0020-0023
(2017/04/11)
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- Isatin 1,2,3-triazoles as potent inhibitors against caspase-3
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Sixteen disubstituted 1,2,3-triazoles were prepared using the Huisgen cycloaddition reaction and evaluated as inhibitors against caspase-3. The two most potent inhibitors were found to be (S)-1-((1-(2,3-dihydrobenzo[b][1,4] dioxin-6-yl)-1H-1,2,3-triazol-4-yl)methyl)-5-((2-(methoxymethyl)pyrrolidin-1-yl) sulfonyl)indoline-2,3-dione (7f) and (S)-1-((1-benzyl-1H-1,2,3-triazol-5-yl) methyl)-5-((2-(methoxymethyl)pyrrolidin-1-yl)sulfonyl)indoline-2,3-dione (8g) with IC50-values of 17 and 9 nM, respectively. Lineweaver-Burk plots revealed that these two triazoles show competitive inhibitory mechanism against caspase-3.
- Jiang, Yang,Hansen, Trond Vidar
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supporting information; experimental part
p. 1626 - 1629
(2011/05/11)
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