4-(1-Aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides: Synthesis, antimicrobial, anticancer evaluation and QSAR studies

A series of 4-(1-aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzenesulfonamide derivatives (1-20) was synthesized and evaluated for its in vitro antimicrobial and anticancer activities. Antimicrobial results indicated that compounds N-(4-(1-benzoyl-5-chloro-2-oxoindolin-3-yl...

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Published in:Arabian Journal of Chemistry
Main Author: Kumar M.; Narasimhan B.; Kumar P.; Ramasamy K.; Mani V.; Mishra R.K.; Majeed A.B.A.
Format: Article
Language:English
Published: Elsevier 2014
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-84905587645&doi=10.1016%2fj.arabjc.2013.03.002&partnerID=40&md5=7bb6098900857b78dabf888acafc5ae6
id 2-s2.0-84905587645
spelling 2-s2.0-84905587645
Kumar M.; Narasimhan B.; Kumar P.; Ramasamy K.; Mani V.; Mishra R.K.; Majeed A.B.A.
4-(1-Aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides: Synthesis, antimicrobial, anticancer evaluation and QSAR studies
2014
Arabian Journal of Chemistry
7
4
10.1016/j.arabjc.2013.03.002
https://www.scopus.com/inward/record.uri?eid=2-s2.0-84905587645&doi=10.1016%2fj.arabjc.2013.03.002&partnerID=40&md5=7bb6098900857b78dabf888acafc5ae6
A series of 4-(1-aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzenesulfonamide derivatives (1-20) was synthesized and evaluated for its in vitro antimicrobial and anticancer activities. Antimicrobial results indicated that compounds N-(4-(1-benzoyl-5-chloro-2-oxoindolin-3-ylideneamino) phenylsulfonyl)-4-isopropoxy benzamide (9) and N-(4-(5-chloro-1-(2-chlorobenzoyl)-2-oxoindolin-3-ylideneamino) phenylsulfonyl)-4-isopropoxybenzamide (19) were found to be the most effective ones. The anticancer results indicated that almost all the synthesized compounds were more active than the standard drug carboplatin but less active than the standard drug 5-fluorouracil (5-FU) against both the cell lines (HCT116 and RAW 264.7). 4-(1-Benzoyl-5-chloro-2-oxoindolin-3-ylideneamino)-N-(pyrimidin-2-yl) benzenesulfonamide (3) was found to be most potent and exhibited selectivity toward HCT 116. QSAR studies indicated that antimicrobial activity of isatin derivatives against different microbial strains was governed by lipophilic parameter, log P and topological parameters valance zero and third order molecular connectivity indices (0χv and 3χv). © 2013 .
Elsevier
18785352
English
Article
All Open Access; Gold Open Access
author Kumar M.; Narasimhan B.; Kumar P.; Ramasamy K.; Mani V.; Mishra R.K.; Majeed A.B.A.
spellingShingle Kumar M.; Narasimhan B.; Kumar P.; Ramasamy K.; Mani V.; Mishra R.K.; Majeed A.B.A.
4-(1-Aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides: Synthesis, antimicrobial, anticancer evaluation and QSAR studies
author_facet Kumar M.; Narasimhan B.; Kumar P.; Ramasamy K.; Mani V.; Mishra R.K.; Majeed A.B.A.
author_sort Kumar M.; Narasimhan B.; Kumar P.; Ramasamy K.; Mani V.; Mishra R.K.; Majeed A.B.A.
title 4-(1-Aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides: Synthesis, antimicrobial, anticancer evaluation and QSAR studies
title_short 4-(1-Aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides: Synthesis, antimicrobial, anticancer evaluation and QSAR studies
title_full 4-(1-Aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides: Synthesis, antimicrobial, anticancer evaluation and QSAR studies
title_fullStr 4-(1-Aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides: Synthesis, antimicrobial, anticancer evaluation and QSAR studies
title_full_unstemmed 4-(1-Aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides: Synthesis, antimicrobial, anticancer evaluation and QSAR studies
title_sort 4-(1-Aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides: Synthesis, antimicrobial, anticancer evaluation and QSAR studies
publishDate 2014
container_title Arabian Journal of Chemistry
container_volume 7
container_issue 4
doi_str_mv 10.1016/j.arabjc.2013.03.002
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-84905587645&doi=10.1016%2fj.arabjc.2013.03.002&partnerID=40&md5=7bb6098900857b78dabf888acafc5ae6
description A series of 4-(1-aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzenesulfonamide derivatives (1-20) was synthesized and evaluated for its in vitro antimicrobial and anticancer activities. Antimicrobial results indicated that compounds N-(4-(1-benzoyl-5-chloro-2-oxoindolin-3-ylideneamino) phenylsulfonyl)-4-isopropoxy benzamide (9) and N-(4-(5-chloro-1-(2-chlorobenzoyl)-2-oxoindolin-3-ylideneamino) phenylsulfonyl)-4-isopropoxybenzamide (19) were found to be the most effective ones. The anticancer results indicated that almost all the synthesized compounds were more active than the standard drug carboplatin but less active than the standard drug 5-fluorouracil (5-FU) against both the cell lines (HCT116 and RAW 264.7). 4-(1-Benzoyl-5-chloro-2-oxoindolin-3-ylideneamino)-N-(pyrimidin-2-yl) benzenesulfonamide (3) was found to be most potent and exhibited selectivity toward HCT 116. QSAR studies indicated that antimicrobial activity of isatin derivatives against different microbial strains was governed by lipophilic parameter, log P and topological parameters valance zero and third order molecular connectivity indices (0χv and 3χv). © 2013 .
publisher Elsevier
issn 18785352
language English
format Article
accesstype All Open Access; Gold Open Access
record_format scopus
collection Scopus
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