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

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 195; no. 9; pp. 767 - 773
• Main Authors: Yurttaş, Leyla, Kubilay, Aslıhan, Evren, Asaf Evrim, Kısacık, İpek, Karaca Gençer, Hülya
• Format: Journal Article
• Language: English
• Published: ABINGDON Taylor & Francis 01.09.2020; Taylor & Francis Ltd
• Subjects: antimicrobial activity; Antimicrobial agents; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Derivatives; Fungicides; Hydrazines; Hydroxyquinoline; Lead compounds; Mass spectrometry; NMR spectroscopy; Physical Sciences; Quinoline; Science & Technology; Synthesis; triazole; Triazoles; 1,2,4-TRIAZOLE DERIVATIVES; DESIGN; ANTIOXIDANT; Quinoline; antimicrobial activity; MOLECULAR DOCKING; triazole
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426507.2020.1756808

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 1 H NMR and 13 C 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.