In:
Acta Pharmaceutica, Walter de Gruyter GmbH, Vol. 63, No. 3 ( 2013-09-1), p. 397-408
Abstract:
A series of novel 5-alkyl/aryl thiadiazole substituted thiazolidin-4-ones were synthesized by a two-step process. In the first step, 5-alkyl/aryl substituted 2-aminothiadiazoles were synthesized, which on reaction with substituted aromatic aldehydes and thioglycolic acid in the presence of dicyclohexylcarbodiimide afforded thiazolidin- 4-ones. All the compounds were synthesized in fairly good yields and their structures were confirmed by spectral and physical data. The title compounds were screened for in vitro anti-proliferative activity on human breast adenocarcinoma cells (MCF-7) by MTT assay. Most of the derivatives showed an IC 50 less than 150 μmol L-1. Among the compounds tested, 2-(2-nitrophenyl)- 3-(5-methyl-1,3,4-thiadiazol-2-yl)-thiazolidin-4-one ( 3f) , 2-(3-fluorophenyl)-3-(5-methyl-1,3,4-thiadiazol-2- -yl)-thiazolidin-4-one ( 3b ), and 2-(4-chlorophenyl)-3- -(5-methyl-1,3,4-thiadiazol-2-yl)-thiazolidin-4-one ( 3c ) were found to be the most active derivatives with IC 50 values of 46.34, 66.84, and 60.71 μmol L -1 , respectively. Antioxidant studies of all the synthesized compounds were carried out by diphenylpicrylhydrazyl (DPPH) assay. Among the compounds tested, 2-phenyl-3-(5-styryl- -1,3,4-thiadiazol-2-yl)-thiazolidin-4-one ( 3s ) elicited superior antioxidant activity with IC 50 of 161.93 μmol L -1 .
Type of Medium:
Online Resource
ISSN:
1846-9558
,
1330-0075
DOI:
10.2478/acph-2013-0028
Language:
Unknown
Publisher:
Walter de Gruyter GmbH
Publication Date:
2013
detail.hit.zdb_id:
2255569-9
SSG:
15,3
Permalink