摘要
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 novel quercetin conjugates 20-27 were successfully synthesized through a concise procedure with 15%-46% overall yields by using Rutin as the starting material. After O-benzylation, glycoside hydrolysis and O-propargylation, rutin was converted to the key intermediate 5,7,3＇,4＇-tetrabenzyloxy-3-O-propargylquercetin, which subsequently ‘clicked＇ with azido containing glycosides, poly（ethylene glycol）（PEG） or oligo（ethylene glycol）（OEG） to provide the fully protected quercetin conjugates 12-19. After global deprotection, the resulting quercetin conjugates were evaluated on hypoglycemic activities at 3T3-L1 adipocyte level. The results showed that conjugates 24, 26 and 27 exhibited good hypoglycemic effects.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2017年第1期133-140,共8页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(Nos.21502139
21402140)
天津市科技特派员(No.15JCTPJC56200)资助项目~~
