title: Synthesis and antimicrobial activity of 1,2,3-triazoles containing quinoline moiety.
abstract: 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.
authors.affiliation: Department of Chemistry, Mangalore University, Mangalagangothri-574199, Karnataka, India.
authors.forename: V
authors.initials: V
authors.lastname: Sumangala
authors.forename: Boja
authors.initials: B
authors.lastname: Poojary
authors.forename: N
authors.initials: N
authors.lastname: Chidananda
authors.forename: Jennifer
authors.initials: J
authors.lastname: Fernandes
authors.forename: N Suchetha
authors.initials: NS
authors.lastname: Kumari
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D006090:Gram-Negative Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D014230:Triazoles