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

  • 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
  • Page Numbers: pp.1093-1102
  • Keywords: antibacterial, anticancer, antifungal, cytotoxicity, HL-60, Thiazole, THP-1
  • Bilecik Şeyh Edebali University Affiliated: Yes

Abstract

© 2021 Taylor & Francis Group, LLC.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.