Design and synthesis of novel 2,4,5-thiazole derivatives as 6-APA mimics and antimicrobial activity evaluation

Nuha D., Evren A. E., Yilmaz Cankilic M., YURTTAŞ L.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.196, no.10, pp.954-960, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 196 Issue: 10
  • Publication Date: 2021
  • Doi Number: 10.1080/10426507.2021.1946537
  • 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.954-960
  • Keywords: Thiazole, 6-APA, antibacterial activity, antifungal activity, physicochemical property prediction, BIOLOGICAL EVALUATION
  • Anadolu University Affiliated: Yes

Abstract

Nine new thiazole derivatives were synthesized considering 6-acetyl penicillanic acid (6-APA) and investigated for their antimicrobial activity. Ethyl 2-(2-mercaptoacetamido)-4-methylthiazole-5-carboxylate derivatives (3a-3i) were gained with a two-step synthetic method using conventional Hantzsch thiazole synthesis. The structural elucidation of the compounds was performed by H-1-NMR, C-13-NMR spectral data and HRMS. All compounds were tested on eleven bacteria and sixteen fungi species and minimum inhibitory concentration (MIC) was determined for each. Compounds 3d (4-methyl-2-(2-((5-methyl-1,3,4-thiadiazol-2-yl), 3f (4-methyl-2-(2-((5-nitro-1H-benzimidazol-2-yl) and 3g (4-methyl-2-(2-((5-methyl-4H-1,2,4-triazol-3-yl) bearing thiazole, 5-nitrobenzimidazole and triazole rings respectively exhibited high antimicrobial activity against most of the strains. In silico physicochemical properties were calculated for the compounds and it was detected that they comply with the rules of drug availability.