Synthesis of Novel <i>N</i>‐Triazolo Methyl Substituted Fluoroquinolones and Their Antimicrobial Activity

Abstract

An elegant synthetic strategy was adopted for the preparation of N ‐triazolo methyl substituted fluoroquinolones 4 and screened for their antimicrobial activity. The synthetic methodology starts from N‐propargylation of ethyl 7‐chloro‐6‐fluoro‐4‐hydroxyquinoline‐3‐carboxylate ( 1 ) followed by reaction with azides through click reaction under Sharpless conditions furnished triazole substituted quinolone ester 3 . The latter quinolone esters were reacted with various secondary amines to furnish the corresponding quinolone derivatives 4 . Alternatively, quinolone carboxylic derivatives 7a , 7b , 7c , 7d were prepared in two steps from triazole tagged quinolone ester. All the final products were screened against various bacterial and fungal strains. Compounds 4a , 4b , 4c and 4k showed moderate antibacterial activity, and 4f showed promising activity against fungal strains.