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, cilt.196, sa.10, ss.954-960, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 196 Sayı: 10
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1080/10426507.2021.1946537
  • 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, Index Chemicus (IC)
  • Sayfa Sayıları: ss.954-960
  • Anahtar Kelimeler: Thiazole, 6-APA, antibacterial activity, antifungal activity, physicochemical property prediction, BIOLOGICAL EVALUATION
  • Anadolu Üniversitesi Adresli: Evet

Özet

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.