Synthesis and antimicrobial activity of 1,2,3-triazoles containing quinoline moiety.

A new series of substituted 1,2,3-triazoles (4a-n) were synthesized from 4-azido-2,8-bistrifluoromethylquinoline 2. The 1,3-dipolar cycloaddition reaction of 2 with ethyl acetoacetate afforded 1-(2,8-Bistrifluoromethylquinolin-4-yl)-5-methyl-1,2,3-triazole-4-carboxylic acid 3, which was then converted into its corresponding acid hydrazide 3a. Condensation of this hydrazide with different aromatic aldehydes resulted in the formation of Schiff's bases, N-[1-Arylmethylene]-1-[2,8-bistrifluoromethylquinoline-4-yl]-5-methyl-1H-1,2,3-triazole-4-carbohydrazides (4a-n). These newly synthesized 1,2,3-triazole derivatives were characterized by analytical and spectral data. All the synthesized compounds were evaluated in vitro for their antibacterial and antifungal activity. A brief investigation of the structure activity relationships revealed that the nature of the substituent on position 4 of the triazole ring influences the antimicrobial activity. Among the newly synthesized compounds, the most active compound was 4n, which contained the 3-methylthien-2-yl moiety and showed a broad spectrum of antimicrobial activity against all the strains used for testing. Compounds 4b, 4c, 4e, 4f, 4h and 4l showed significant antimicrobial activity at the concentration of 6.25 μg/mL.