An approach to C-glycosidic conjugates of isoflavones

Abstract

A novel approach to isoflavone glycoconjugates, designed as less biodegradable congeners of natural glycosides, is presented on example of daidzein linkage to a C-glycosidic synthon derived from l-rhamnose. 1,3-Dipolar cycloaddition was employed for chemical ligation of daidzein 7-O-propargyl ester and alkyl azide containing 2,3-unsaturated pyranoside moiety. The obtained constructs with opposite anomeric configuration both exhibited a considerable increase in cytotoxic activity against the HTC 116 cell line, in comparison to the parent isoflavone.