Synthesis of some novel 3,4,5-trisubstituted triazole derivatives bearing quinoline ring and evaluation of their antimicrobial activity

YURTTAŞ L., Kubilay A., Evren A. E., Kisacik I., Karaca Gencer H.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.195, no.9, pp.767-773, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 195 Issue: 9
  • Publication Date: 2020
  • Doi Number: 10.1080/10426507.2020.1756808
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Index Chemicus (IC)
  • Page Numbers: pp.767-773
  • Keywords: Quinoline, triazole, antimicrobial activity, 1,2,4-TRIAZOLE DERIVATIVES, MOLECULAR DOCKING, ANTIOXIDANT, DESIGN
  • Anadolu University Affiliated: Yes


Some new 3,4,5-trisubstituted 1,2,4-triazole derivatives were synthesized and studied for their antimicrobial activity. The lead compounds were obtained starting from 8-hydroxyquinoline and ethyl 2-chloroacetate. The obtained ester compound (1) first reacted with hydrazine hydrate (2) then with phenyl isothiocyanate (3). Ring closure by KOH led to 3-mercapto-1,2,4-triazole derivative (4). Lastly, it reacted with 2-chloro-N-(substituted (benzo)/thiazole)acetamide derivatives to obtain the final compounds (5a-j). The structural elucidation of the compounds was performed by H-1 NMR and C-13 NMR spectroscopy and high resolution mass spectrometry techniques and elemental analysis. The synthesized compounds were investigated for their antimicrobial activities against seven bacteria and four fungi. As a result of the activity studies, it was observed that compounds N-(6-nitrobenzothiazol-2-yl)-2-[[4-phenyl-5-((quinolin-8-yloxy)methyl)-4H-1,2,4-triazol-3-yl]thio]acetamide (5a) and N-(6-fluorobenzothiazol-2-yl)-2-[[4-phenyl-5-((quinolin-8-yloxy)methyl)-4H-1,2,4-triazol-3-yl]thio]acetamide (5d) were the most active molecules. Also, the antifungal activity of the compounds was found to be higher than their antibacterial activity although lower than the standard drug's potential. Additionally, the physicochemical properties of the compounds were calculated which were evaluated to be at a suitable range for oral administration.