POTENT IN VITRO BIOLOGICAL ACTIVITY OF SOME DERIVATIVES OF SYNTHESIZED C-9154 ANTIBIOTIC

Abstract

This research was undertaken to design several new antibiotics, by structurally modifying the C-9154 antibiotic simultaneously improving activity and lowering toxicity as part of our continued attempts at designing new antibiotics. An analogue to the C-9154 antibiotic and six derivatives of this analogue were synthesized. The approach was to significantly reduce the polarity of the synthesized analogue in the derivatives to achieve increased permeability across cell membranes by conversion of the highly polar carboxylic group to an ester functional group. The compounds were synthesized by condensation of 3-aminophenol with maleic anhydride and then conversion of the terminal carboxylic acid functional group to ester functional group using a thionyl chloride-mediated esterification process. The in vitro biological activity showed that the derivatives were more active than the analogue and significantly better than the standard drugs used for comparison. The compounds were fully characterized using Infrared, GC-MS and 1D and 2D NMR experiments.KEYWORDS: Antibiotics, Bioactivity, C-9154, Maleic anhydride, NMR, Synthesis