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, cilt.194, sa.8, ss.820-828, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 194 Sayı: 8
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1080/10426507.2018.1550642
  • Dergi Adı: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Sayfa Sayıları: ss.820-828
  • Anahtar Kelimeler: Azoles, anticancer activity, thiazole, apoptosis, OVERCOMING DRUG-RESISTANCE, IN-VITRO, CANCER, INHIBITORS, APOPTOSIS, IDENTIFICATION, CYTOTOXICITY, DISCOVERY, TOXICITY, SURVIVAL
  • Anadolu Üniversitesi Adresli: Evet

Özet

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.