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经过五步反应以15%~46%的总收率成功合成了8个新型的槲皮素缀合物20~27.以芦丁为起始原料,经O-苄基化、酸催化糖苷水解、烷基化等步骤,获得重要中间体5,7,3’,4’-四苄氧基-3-O-炔丙基槲皮素;再经过Click反应,得到槲皮素缀合物中间体12~19,最后经催化氢化得到系列糖基、聚乙二醇(PEG)或寡聚乙二醇(OEG)与槲皮素偶联的新型缀合物.经体外3T3-L1脂肪细胞水平降糖活性测试,结果显示缀合物24,26和27具有较好的降糖活性.
Eight new quercetin conjugates 20-27 were successfully synthesized in 15% ~ 46% overall yield after five steps.Using rutin as the starting material, O-benzylation and acid-catalyzed hydrolysis of glycoside , Alkylation and other steps to obtain the important intermediate 5,7,3 ’, 4’-tetrabenzyloxy-3-O-propargyl quercetin; and then Click reaction to obtain quercetin conjugate intermediate And then a series of new glycosyl conjugates were obtained by catalytic hydrogenation of glycosides, polyethylene glycol (PEG) or oligoethylene glycol (OEG) and quercetin.After in vitro 3T3-L1 adipocyte level Hypoglycemic activity test showed that conjugates 24, 26 and 27 had good hypoglycemic activity.