Acta Pharm. 63 (2013) 397-408
Original research paper
Synthesis, in
vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones
ALEX JOSEPH, CHAITANYAKUMAR S. SHAH, SUTHAR SHARAD KUMAR, ANGEL
TREASA ALEX, NASEER MALIYAKKAL, SUDHEER MOORKOTH and JESSY ELIZABETH MATHEW
Manipal College of
Pharmaceutical Sciences, Manipal University, Manipal, India
Accepted May 13, 2013
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-amino-thiadiazoles were synthesized, which on
reaction with substituted aromatic aldehydes and thioglycolic acid in 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 IC50
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 most active
derivatives with IC50 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 IC50 of 161.93
µmol L–1.
Keywords: thiadiazole, thiazolidin-4-ones, anticancer, antioxidant