Design and synthesis of benzyl 4-O-lauroyl-α-L-rhamnopyranoside derivatives as antimicrobial agents

Abstract

Benzyl α-L-rhamnopyranoside, prepared by both conventional and microwave assisted glycosidation techniques, was converted into benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside which after lauroylation followed by removal of isopropylidene group gave the benzyl 4-O-lauroyl-α-L-rhamnopyranoside in good yield. Several derivatives of benzyl 4-O-lauroyl-α-L-rhamnopyranoside were prepared and assessed in vitro for their antimicrobial activity against ten human pathogenic bacteria and seven fungi. The structure activity relationship (SAR) study revealed that incorporation of 4-O-lauroyl group in rhamnopyranoside frame work along with 2,3-di-O-acyl group increased the antifungal potentiality of the rhamnopyranosides.

Keywords

• Benzyl α-L-rhamnopyranoside
• Lauroylation
• Antimicrobial agents
• Structure activity relationship (SAR)