Synthesis and Anti-HCV Activity of Analogues of the Natural Phenolic β-D-Glucopyranosides

Phenolic beta-D-glucopyranosides exist widely in nature and exhibit many important physiological activities. For example, gastrodia isolated from Pholidota chinensis Lind1. has such a sketch and play an important bioactivity on nerve system. Recently, we found another phenolic beta-D-glucopyranoside from the Pulicaria insignis which had definite anti-HCV activity. Based on the results achieved in our research group, we tried to design and synthesize series of phenolic beta-D-glucopyranosides to wish to find new and better bioactive compounds used in anti-HCV study. Fifteen novel natural analogues of phenolic beta-D-glucopyranosides were synthesized from phenolic aglycones and acetobromo-alpha-D-glucose or beta-D-glucose pentaacetate. Their structures were characterized by MS, H-1 NMR and C-13 NMR. Preliminary anti-HCV activity tests showed that compounds 8a and 10a exhibited definite anti-viral activity, their EC50 are 21 and 9.4 mu mol/L, and the CC50 of them are 150.4 and 145.9 mu mol/L, respectively.