Domino Multicomponent Approach for the Synthesis of Functionalized Spiro-Indeno12-bquinoxaline Heterocyclic Hybrids and Their Antimicrobial Activity Synergistic Effect and Molecular Docking Simulation

摘要

An expedient synthesis of hitherto unexplored novel hybrid heterocycles comprising dispiropyrrolidine, N-styrylpiperidone and indeno[1,2-b]quinoxaline units has been developed via domino multicomponent 1,3-dipolar cycloaddition strategy employing a new class of azomethine ylide in ionic liquid, 1-butyl-3-methylimidazolium bromide. This domino protocol involves, 1,3-dipolar cycloaddition and concomitant enamine reaction affording the dispiropyrrolidine tethered N-styrylpiperidone hybrid heterocycles in moderate to good yield in a single step. These compounds were evaluated for their antimicrobial activity against bacterial and fungal pathogens, therein compounds >8f, >8h, and >8l displayed significant activity against tested microbial pathogens. The synergistic effect revealed that the combination of compound >8h with streptomycin and vancomycin exhibited potent synergistic activity against E. coli ATCC 25922. In addition, molecular docking simulation has also been studied for the most active compound.