Synthesis and biological evaluation of thiazole and thiadiazole derivatives as potential anticancer agents. (4th March 2023)

• Record Type: Journal Article
• Authors: Ekrek, Sedanur; Şenkardeş, Sevil; Erdoğan, Ömer; Çevik, Özge
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 198:Number 3(2023)
• Page Start: 223
• Page End: 231
• Publication Date: 2023-03-04
• Subjects: Anticancer activity -- thiadiazole -- thiazole -- apoptosis -- thiosemicarbazone; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2022.2136665
• Languages: English
• ISSNs: 1042-6507

Abstract

Abstract: 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. GRAPHICAL ABSTRACT: UF0001