Synthesis of Novel N‐Triazolo Methyl Substituted Fluoroquinolones and Their Antimicrobial Activity |
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Authors: | A Ravi Kumar G. Sathaiah A. Chandra Shekhar K. Raju P. Shanthan Rao B. Narsaiah Y. K. Raju U. S. N. Murthy |
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Affiliation: | 1. Fluoroorganics Division, Indian Institute of Chemical Technology, Hyderabad, India;2. Biology Division (Bioinformatics), Indian Institute of Chemical Technology, Hyderabad, India |
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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. |
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