Abstract

DESIGN, SYNTHESIS AND IN VITRO ANTI-MICROBIAL STUDY OF NEW METRONIDAZOLE-AMINO ESTER PRODRUGS

Yasir K. Mahdi and Najwan Jubair*

ABSTRACT

Three amino acid ester prodrugs of metronidazole (I-III) were synthesized by reaction of amino acids (glycine, alanine and valine) respectively with metronidazole in presence of 4-Dimetheylaminopyridine (DMAP) as catalyst and Dimethylformamide (DMF) as solvent. The structures of the synthesized prodrugs were confirmed using FT-IR and 1HNMR spectroscopy. The resulting prodrugs were evaluated for their antimicrobial activity toward C. difficle, B. fragilis and E. histolytica species. Valine amino ester prodrug of metronidazole (III) showed higher antimicrobial activity compared to parent compound.

Keywords: Synthesis, metronidazole, amino acids, ester prodrugs, antimicrobial activity.