Acta Pharmaceutica, Vol. 63 No. 3, 2013.
Izvorni znanstveni članak
https://doi.org/10.2478/acph-2013-0028
Synthesis, in vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones
ALEX JOSEPH
; Manipal College of Pharmaceutical Sciences, Manipal University, Manipal, India
CHAITANYAKUMAR S. SHAH
; Manipal College of Pharmaceutical Sciences, Manipal University, Manipal, India
SUTHAR SHARAD KUMAR
; Manipal College of Pharmaceutical Sciences, Manipal University, Manipal, India
ANGEL TREASA ALEX
; Manipal College of Pharmaceutical Sciences, Manipal University, Manipal, India
NASEER MALIYAKKAL
; Manipal College of Pharmaceutical Sciences, Manipal University, Manipal, India
SUDHEER MOORKOTH
; Manipal College of Pharmaceutical Sciences, Manipal University, Manipal, India
JESSY ELIZABETH MATHEW
; Manipal College of Pharmaceutical Sciences, Manipal University, Manipal, India
Sažetak
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 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 the MTT assay. Most 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 the most active derivatives with IC50 values of 46.34, 66.84, and 60.71 µmol L–1, respectively. Antioxidant studies of all synthesized compounds were carried out using diphenylpicrylhydrazyl 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.
Ključne riječi
thiadiazole; thiazolidin-4-ones; anticancer; antioxidant
Hrčak ID:
102031
URI
Datum izdavanja:
30.9.2013.
Posjeta: 2.314 *