21 Citations (Scopus)

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 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 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.

Original languageEnglish
Pages (from-to)397-408
Number of pages12
JournalActa Pharmaceutica
Volume63
Issue number3
DOIs
Publication statusPublished - 01-09-2013

Fingerprint

Thiadiazoles
Inhibitory Concentration 50
Antioxidants
2-amino-1,3,4-thiadiazole
Dicyclohexylcarbodiimide
MCF-7 Cells
Human Activities
Aldehydes
Adenocarcinoma
Breast
In Vitro Techniques

All Science Journal Classification (ASJC) codes

  • Medicine(all)
  • Pharmacology
  • Pharmaceutical Science

Cite this

@article{6e2d746decbe4a63aea7d4f7d6aeec81,
title = "Synthesis, in vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones",
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 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 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.",
author = "Alex Joseph and Shah, {Chaitanyakumar S.} and Kumar, {Suthar Sharad} and Alex, {Angel Treasa} and Naseer Maliyakkal and Sudheer Moorkoth and Mathew, {Jessy Elizabeth}",
year = "2013",
month = "9",
day = "1",
doi = "10.2478/acph-2013-0028",
language = "English",
volume = "63",
pages = "397--408",
journal = "Acta Pharmaceutica",
issn = "1330-0075",
publisher = "Croatian Pharmaceutical Society",
number = "3",

}

Synthesis, in vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones. / Joseph, Alex; Shah, Chaitanyakumar S.; Kumar, Suthar Sharad; Alex, Angel Treasa; Maliyakkal, Naseer; Moorkoth, Sudheer; Mathew, Jessy Elizabeth.

In: Acta Pharmaceutica, Vol. 63, No. 3, 01.09.2013, p. 397-408.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis, in vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones

AU - Joseph, Alex

AU - Shah, Chaitanyakumar S.

AU - Kumar, Suthar Sharad

AU - Alex, Angel Treasa

AU - Maliyakkal, Naseer

AU - Moorkoth, Sudheer

AU - Mathew, Jessy Elizabeth

PY - 2013/9/1

Y1 - 2013/9/1

N2 - 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 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 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.

AB - 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 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 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.

UR - http://www.scopus.com/inward/record.url?scp=84887373544&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84887373544&partnerID=8YFLogxK

U2 - 10.2478/acph-2013-0028

DO - 10.2478/acph-2013-0028

M3 - Article

VL - 63

SP - 397

EP - 408

JO - Acta Pharmaceutica

JF - Acta Pharmaceutica

SN - 1330-0075

IS - 3

ER -