Efficient synthesis and antimicrobial evaluation of 2-((1-substituted-1H-1,2,3-triazol-4-yl)-1-naphthaldehydes and their oxime derivatives

A series of 2-((1-substituted-1H-1,2,3-triazol-4-yl)-1-naphthaldehydes was prepared by the propargylation of 2-hydroxynaphthaldehyde followed by Copper(I)-catalyzed azide-alkyne cycloaddition with various organic azides. 2-((1-substituted-1H-1,2,3-triazol-4-yl)-1-naphthaldehyde analogues were transformed to corresponding oxime derivatives upon grinding with hydroxylamine hydrochloride under solvent free conditions. All the synthesized compounds were characterized by various analytical and spectral techniques and screened in vitro for antimicrobial activity. The activity data revealed that most of the compounds exhibited good to significant activities. Compounds 4c and 5c exhibited very good and broad spectrum activity towards all the tested bacterial strains. Further, to understand the binding interactions, 4c and 5c were docked into the active sites of E. coli topoisomerase II DNA gyrase.