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Investigation of N ‐Arylsulfonylimidazole as Novel Scaffold for Anticancer Agents
Author(s) -
Subramanian Santhosh,
Yang HyunSun,
Manickam Manoj,
Yun Jieun,
Jung SangHun
Publication year - 2016
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.10734
Subject(s) - moiety , chemistry , stereochemistry , imidazole , cytotoxicity , indoline , stereocenter , isostere , in vitro , biochemistry , enantioselective synthesis , catalysis
To explore the possibility of isosteric replacement of imidazolidinone moiety of ( S )‐1‐(1‐(4‐aminobenzoyl)indolin‐5‐ylsulfonyl)‐4‐phenylimidazolidin‐2‐one ( 1 ) for the anticancer activity, novel 1‐(1‐acyl substituted indolin‐5‐sulfonyl)‐4‐phenyl‐1 H ‐imidazoles 2 were prepared with varying the N ‐acyl group on the indoline ring and evaluated for their in vitro anticancer activity against six human cancer cell lines (renal ACHN , colon HCT ‐15, breast MDA‐MB ‐231, lung NCI‐H23 , stomach NUGC ‐3, and prostrate PC ‐3). Among the analogs prepared, imidazoles with hydrophobic acyl substituents on indoline like cyclohexanecarbonyl ( 2e , mean 50% growth inhibition [ GI 50 ] = 2.29 μM ) or benzoyl with electron‐donating groups like 4‐methoxybenzoyl ( 2g , mean GI 50 = 4.11 μM ) and 4‐aminobenzoyl ( 2a , mean GI 50 = 4.45 μM ) exhibited relatively good cytotoxicity. Although imidazole moiety of arylsulfonylphenylimidazole 2 contains only hydrogen bonding acceptor property without a stereogenic center unlike imidazolidinone analogs, the high level of the activity of 2 proved that the imidazole motif is obviously good isostere of imidazolidinone moiety of arylsulfonylphenylimidazolidinone 1 for the anticancer activity.