Synthesis and in vitro microbiological evaluation of imidazo(4,5-b)pyridinylethoxypiperidones

A series of imidazo(4,5-b)pyridinylethoxypiperidones was designed, synthesized and characterized for evaluation of potential antibacterial activity against Bacillus subtilis, Klebsiella pneumoniae, Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa and antifungal activity against Candida albicans-6, Candida albicans, Aspergillus niger, Candida albicans-51 and Aspergillus flavus. Structure–activity relationship led to the conclusion that compound 39 exerted strong in vitro antibacterial activity against Bacillus subtilis and Staphylococcus aureus whereas compounds 38 and 39 displayed promising antifungal activity against Aspergillus flavus. The interesting antimicrobial profile of compound 39 led us to select this derivative for further development.

2,6-Diarylpiperidin-4-ones upon strategical N-hydroxylation, cyanoethylation followed by acid assisted cyclocondensation with 2,3-diaminopyridine afforded an efficient route to synthesis novel 1-[2-(imidazo(4,5-b)pyridin-2-yl)ethoxy]-2,6-diarylpiperidin-4-ones. The synthesized compounds were evaluated for their antibacterial and antifungal activity. Structure-activity relationship led to the conclusion that compound 39 exerted a strong in vitro antibacterial activity against Bacillus subtilis and Staphylococcus aureus whereas compounds 38 and 39 displayed promising antifungal activity against Aspergillus flavus.Figure optionsDownload as PowerPoint slide