Synthesis and biological evaluation of 5-methyl-4-phenyl thiazole derivatives as anticancer agents


Evren A. E., YURTTAŞ L., Ekselli B., AKALIN ÇİFTÇİ G.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.194, no.8, pp.820-828, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 194 Issue: 8
  • Publication Date: 2019
  • Doi Number: 10.1080/10426507.2018.1550642
  • Journal Name: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.820-828
  • Keywords: Azoles, anticancer activity, thiazole, apoptosis, OVERCOMING DRUG-RESISTANCE, IN-VITRO, CANCER, INHIBITORS, APOPTOSIS, IDENTIFICATION, CYTOTOXICITY, DISCOVERY, TOXICITY, SURVIVAL
  • Anadolu University Affiliated: Yes

Abstract

New N-(5-methyl-4-phenylthiazol-2-yl)-2-(substituted thio)acetamides were synthesized and studied for their anticancer activity. The title compounds were procured by reacting 2-chloro-N-(5-methyl-4-phenylthiazol-2-yl)acetamide with some mercapto derivatives. The structural elucidation of the compounds was performed by H-1-NMR, C-13-NMR and LC-MS/MS spectral data and elemental analyses. The synthesized compounds were investigated for their antitumor activities against A549 human lung adenocarcinoma cells and NIH/3T3 mouse embryoblast cell line for determining their selective cytotoxicity. 2-[(1-methyl-1H-tetrazol-5-yl)thio]-N-(5-methyl-4-phenylthiazol-2-yl)acetamide (4c) showed high selectivity, and whose IC50 value was determined as 23.30 +/- 0.35 mu M and >1000 mu M against A549 human lung adenocarcinoma cells and NIH/3T3 mouse embryoblast cell lines, respectively. 2-[(1-Methyl-1H-imidazol-2-yl)thio]-N-(5-methyl-4-phenyl thiazol-2-yl)acetamide (4a) and 2-[(1-Methyl-1H-tetrazol-5-yl)thio]-N-(5-methyl-4-phenyl thiazol-2-yl)acetamide (4c) exhibited the highest apoptosis percentage among those tested, but not as high as the standard, cisplatin.