Regioselective Synthesis of Some Rhamnopyranoside Esters for PASS Predication, and ADMET Studies

Abstract

Notable biological activities including brains protective activities have made carbohydrate estersas a topic of great interest over the past several decades. In this context, unimolecular treatment of methylα-L-rhamnopyranoside with dibutyltin oxide gave the corresponding 2,3-O-(dibutylstannylene) derivativewhich was then allowed to react with 3-chlorobenzoyl chloride. The reaction regioselectively furnished the 3-O-substitution product in excellent yield. To get newer rhamnopyranoside esters chlorobenzoate was furtherconverted into four 2,4-di-O-substituted products with other acylating agents using direct acylationtechnique. Moreover, thermodynamic properties indicated that these sugar esters (SEs) possess betterstability, suitable polar nature and higher binding affinity than the non-ester rhamnopyranoside. Predictionof Activity Spectra for Substances (PASS) predication showed that these SEs should be more potent againstfungal pathogens than the bacterial organisms. With these encouraging results absorption, distribution,metabolism, excretion, and toxicity (ADMET) and drug-likeness properties of the SEs are also discussed.