β-D-吡喃型葡萄糖酚苷类天然类似物的合成及抗HCV病毒活性

摘要

以α-溴代四乙酰基葡萄糖(或-D-葡萄糖五乙酸酯)和酚为原料,经2步反应合成了15个新的β-D-吡喃型葡萄糖酚苷类天然产物类似物,采用质谱(MS)及核磁共振(NMR)等手段对其结构进行了表征.生物活性测定结果表明,化合物8a和10a对丙型肝炎病毒(HCV)有一定的抑制作用,它们的EC50值分别为21和9.4 μmoVL,CC50值分别为150.4和145.9 μmol/L.%Phenolic β-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 β-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 β-D-glucopyranosides to wish to find new and better bioactive compounds used in anti-HCV study. Fifteen novel natural analogues of phenolic β-D-glucopyranosides were synthesized from phenolic aglycones and acetobromo-α-D-glucose or β-D-glucose pentaacetate. Their structures were characterized by MS, 1H NMR and 13C NMR. Preliminary anti-HCV activity tests showed that compounds 8a and 10a exhibited definite anti-viral activity, their EC50 are 21 and 9.4 μmol/L, and the CC50 of them are 150.4 and 145. 9 μmol/L, respectively.