苯丙烯类葡萄糖氧苷的合成及其抗缺氧活性

以取代苯甲醛(1a~1t)为原料，通过Knoevenagel缩合、酯化和LiAlH₄还原等反应制得苯丙烯醇衍生物(3a~3t)；以取代肉桂醛(1u~1x)为原料，经NaBH₄还原制得苯丙烯醇衍生物(3u~3x); 3a~3x与全乙酰化溴代葡萄糖经Koenigs-Knorr偶联反应及MeONa/MeOH体系脱除乙酰保护基反应，合成了24个苯丙烯类葡萄糖氧苷(5a~5x)，其中5c，5f ~ 5x为新化合物，其结构经¹H NMR和ESI-MS表征。采用MTT法测定了5对缺氧损伤的内皮细胞(EA.hy926)的抗缺氧活性。实验结果表明： 5b, 5e, 5g, 5p, 5q, 5s, 5t和5y对EA.hy926的抗缺氧活性均高于经景天苷。

Synthesis of Benzene Propylene O-Glycosides and Their Anti-hypoxic Activities

Twenty four benzene propylene O-glycosides(5a~5x) were designed and synthesized by Koenigs-Knorr reaction of 3-phenyl-2-propen-1-ol derivatives (3a ~3x) with bromo acetyl glucose and deacetylation.3a~3x were prepared by two methods.3a~3t were prepared by Knoevenagel con-densation, esterification, and reduction from substituted benzaldehyde.And 3u~3x were prepared by reduction from cinnamic aldehyde derivatives.5c, 5f~5x were new compounds.The structures were characterized by 1 H NMR and ESI-MS.The anti-hypoxic activities of 5 on hypoxia exposure endothelial cells( EA.hy926) were evaluated by MTT assays.The results indicated that 5b, 5e, 5g, 5p, 5q, 5s, 5t and 5y exhibited better anti-hypoxic activity than salidroside.