Synthesis of imidazole-fused nitrogen-bridgehead heterocycles catalysed by lipase and their antifungal and antimicrobial bioactivity

Abstract

An effective approach for selective C-N bond formation for synthesising imidazo[1,2-a] pyridine-based heterocycles using porcine pancreatic lipase (PPL) as a biocatalyst has been devised. Under moderate conditions, a series of imidazo[1,2-a]pyridine-based heterocycle derivatives were synthesised with remarkable selectivity in good-to-excellent yields (89-95%). Further, the antimicrobial and antifungal activities of derivatives 3ha, 3ka, 3fa, 3hc, and 3eb were observed, and they were found to be biologically active in antimicrobial susceptibility tests for Gram-positive bacteria (Enterococcus faecalis ATCC 29212 and Staphylococcus auris ATCC 25923), Gram-negative bacteria (Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) and fungal strains (Candida albicans ATCC 90028 and Candida tropicalis ATCC 750). © 2024 The Royal Society of Chemistry.