Synthesis of new thiazole derivatives and evaluation of their antimicrobial and cytotoxic activities

Dawbaa S., Evren A. E., CANTÜRK Z., YURTTAŞ L.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.196, no.12, pp.1093-1102, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 196 Issue: 12
  • Publication Date: 2021
  • Doi Number: 10.1080/10426507.2021.1972299
  • Journal Name: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Index Chemicus (IC)
  • Page Numbers: pp.1093-1102
  • Keywords: Thiazole, antibacterial, antifungal, cytotoxicity, anticancer, THP-1, HL-60, BIOLOGICAL EVALUATION, DESIGN, DISCOVERY, INHIBITORS, CHEMISTRY, TRIAZOLE
  • Anadolu University Affiliated: Yes

Abstract

Novel 2-heteroaryl-N-[4-(substituted aryl)thiazol-2-yl]propanamide derivatives (7a-7o) were synthesized and investigated for their antimicrobial activity. Among the tested compounds, 2-[(1H-Benzimidazol-2-yl)thio]-N-[4-(naphthalen-2-yl)thiazol-2-yl]propanamide (7e) and N-[4-(4-Chlorophenyl)thiazol-2-yl]-2-[(1-methyl-1H-tetrazol-5-yl)thio]propanamide (7f) showed the highest antibacterial activity, whereas 2-[Benzothiazol-2-ylthio]-N-[4-(4-chlorophenyl)thiazol-2-yl]propanamide (7i) and 2-[(1H-Benzimidazol-2-yl)thio]-N-[4-(4-chlorophenyl)thiazol-2-yl]propanamide (7j) displayed anticandidal effect against C. parapsilosis and C. glabrata. The cytotoxic activity of the compounds (7a-7o) was also tested against HL-60 human leukemia cells, THP-1 human monocytic leukemia cells, and NIH/3T3 mouse embryonic fibroblast cells. Compound N-[4-(4-Chlorophenyl)thiazol-2-yl]-2-[(1-methyl-1H-imidazol-2-yl)thio]propanamide (7 g) and compound 7j exhibited high cytotoxicity against HL-60; and compounds 2-[(1-Methyl-1H-imidazol-2-yl)thio]-N-[4-(naphthalen-2-yl)thiazol-2-yl]propanamide (7b), 7 g and N-[4-(4-Methoxyphenyl)thiazol-2-yl]-2-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]propanamide (7 m) also had cytotoxic activity against THP-1 compared with standard drug with selective profile. Additionally, in silico physicochemical properties of the compounds were described.