Synthesis and biological evaluation of thiazole and thiadiazole derivatives as potential anticancer agents

Ekrek S., ŞENKARDEŞ S., ERDOĞAN Ö., ÇEVİK Ö.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, cilt.198, sa.3, ss.223-231, 2023 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 198 Sayı: 3
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1080/10426507.2022.2136665
  • Dergi Adı: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core
  • Sayfa Sayıları: ss.223-231
  • Anahtar Kelimeler: Anticancer activity, thiadiazole, thiazole, apoptosis, thiosemicarbazone, STRUCTURAL-CHARACTERIZATION, HYBRIDS, 1,3,4-THIADIAZOLE, INHIBITION, CANCER, BAX
  • Marmara Üniversitesi Adresli: Evet

Özet

A new series of 4-methyl-2-{2-[(aryl)methylidene]hydrazinyl}-1,3-thiazole (2a-i), N-(4-acetyl-5-aryl)4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamides (3a-b) and N-(5-(4-(substituted phenyl)-1,3,4-thiadiazol-2-yl)acetamides (3c-i) were synthesized by the reaction of 2-((aryl)methylene)hydrazine-1-carbothioamides (1a-i) and acetic anhydride or chloroacetone. The cytotoxic activities of the products were evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay against Hela cervical cancer, MCF-7 breast carcinoma and HT-29 colorectal cancer cell lines. Thiazole based compounds 2a, 2b, 2f and 2i, bearing 4-bromothiophen-2-yl, naphthalen-2-yl, 2,5-difluorophenyl and 4-(trifluoromethoxy)phenyl moieties, respectively; also N-(4-acetyl-5-(naphthalen-2-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide (3b) and N-(5-(2,6-difluorophenyl)-1,3,4-thiadiazol-2-yl)acetamide (3d) exhibited significant anticancer activity against three cancer cell lines. Moreover, these active compounds were further evaluated by apoptotic protein levels. The results showed that these thiazole and thiadiazole compounds induced apoptosis of cancer cells.