Synthesis of novel N-(naphthalen-1-yl)propanamide derivatives and evaluation their antimicrobial activity

Evren A. E., YURTTAŞ L., Yilmaz-Cankilic M.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, cilt.195, sa.2, ss.158-164, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 195 Sayı: 2
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1080/10426507.2019.1657428
  • Dergi Adı: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Index Chemicus (IC)
  • Sayfa Sayıları: ss.158-164
  • Anahtar Kelimeler: Naphthalene, propanamide, antimicrobial activity, IN-VITRO, BIOLOGICAL EVALUATION, MOLECULAR DOCKING, ANTIBACTERIAL, ANTIFUNGAL, PEPTIDES, DESIGN, 1,2,4-TRIAZOLE, INHIBITORS, NAFTIFINE
  • Anadolu Üniversitesi Adresli: Evet

Özet

New N-(naphthalen-1-yl)propanamide was synthesized and studied for their antimicrobial activity. The final compounds were procured by reacting N-(naphthalen-1-yl)propanamide with some 2-mercapto aryl or dithiocarbamate salt derivatives. Their structures were determined by H-1-NMR and C-13-NMR spectroscopy and LC-MS/MS spectral data. The synthesized compounds were investigated for their antimicrobial activities against 10 bacteria and 10 fungi species. All compounds showed notable activity. Especially, compounds 2-[(5-methyl-1,3,4-thiadiazol-2-yl)thio]-N-(naphthalen-1-yl)propanamide (2a), 2-(benzothiazol-2-ylthio)-N-(naphthalen-1-yl)propenamide (2b), 2-[(1-methyl-1H-imidazol-2-yl)thio]-N-(naphthalen-1-yl)propanamide (2c), and N-(naphthalen-1-yl)-2-[(5-nitro-1H-benzimidazol-2-yl)thio]propanamide (2e) exhibited antifungal activity against at least one fungus at the half potency of ketoconazole. Also, 2-[(1-methyl-1H-imidazol-2-yl)thio]-N-(naphthalen-1-yl)propanamide (2c), N-(naphthalen-1-yl)-2-[(5-nitro-1H-benzimidazol-2-yl)thio]propanamide (2e) and 2-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]-N-(naphthalen-1-yl)propanamide (2f) showed anti-gram-positive bacterial activity at the half potency of chloramphenicol. Only one compound, 2-(benzothiazol-2-ylthio)-N-(naphthalen-1-yl)propanamide (2b) displayed anti-gram-negative bacterial activity against Yersinia enterocolitica (Y53).