苯丙烯类葡萄糖氧苷的合成及其抗缺氧活性  

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

作　　者：马臣[1,2] 张文彬[1,2] 李霞[2] 李灵芝[2,3] 吴宇强[1,2] 张永亮[3] 葛肖健 

机构地区：[1]天津医科大学药学院,天津300070 [2]武警后勤学院药物化学教研室,天津300193 [3]武警后勤学院天津市职业与环境危害防制重点实验室,天津300309 [4]天津中医药大学药学院,天津300193

出　　处：《合成化学》2016年第3期203-210,共8页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(81471823);天津市重点基金项目(12JCZDJC34700);武警后勤学院科研创新团队项目(WHTD210303)

摘　　要：以取代苯甲醛(1a^1t)为原料,通过Knoevenagel缩合、酯化和Li Al H4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Na BH4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Me ONa/Me OH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红景天苷。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 condensation,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 by1 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.

关 键 词：苯丙烯类 红景天苷 合成 内皮细胞 抗缺氧活性 

分 类 号：O629.13[理学—有机化学] R914.5[理学—化学]