摘要
以丁炔二醇为起始原料,用叔丁基二甲基氯硅烷进行单保护后,与2-(6-羟基-2,3-二氢苯并呋喃)乙酸甲酯经Mitsunobu反应制得2-{6-[4-(叔丁基二甲硅烷氧基)丁-2炔基氧基]-2,3-二氢苯并呋喃}乙酸甲酯(3);3脱除保护后与苯酚衍生物发生Mitsunobu反应,随后经水解合成了6个结构新颖的苯并二氢呋喃衍生物(7a^7f),其结构经1H NMR,13C NMR和HR-EI-MS表征。GPR40激动活性测试结果表明:7a^7f对GPR40均有激动作用,其中7e和7f激动活性最强,EC50分别为0.593μmol·L-1和0.596μmol·L-1。
Methyl 2-{ 6-[4-( tert-butyldimethylsilyloxy) but-2-ynyloxy]-2,3-dihydrobenzofuran-3-yl }acetate( 3) was prepared by protection of 2-butyne-1,4-diol with tert-butyldimethylsilyl chloride,then Mitsunobu reaction with methyl 2-( 6-hydroxy-2,3-dihydrobenzofuran-3-yl) acetate. Six novel benzo-dihydrofuran derivatives( 7a ~ 7f) were synthesized by deprotection,Mitsunobu reaction with phenol derivatives and hydrolysis from 3. The structures were characterized by1 H NMR,13 C NMR and HR-EIMS. The activities of 7a ~ 7f were tested in GPR40-transfected HEK293 cells. The results showed that7 a ~ 7f all exhibited agonistic activities on GPR40,7e and 7f were the most potent componds,with the EC50 of 0. 593 μmol·L- 1and 0. 596 μmol·L- 1,respectively.
出处
《合成化学》
CAS
CSCD
2016年第1期1-5,共5页
Chinese Journal of Synthetic Chemistry
基金
国家自然科学基金资助项目(2140222)
