3-(4-β-D-吡喃阿洛糖苷苯基)-4-胺羰基-5-甲氧羰基异噁唑衍生物的合成及其镇静活性的研究有机化学.pdfVIP

2009 年第 29 卷 有 机 化 学 Vol. 29, 2009 第 1 期, 89～93 Chinese Journal of Organic Chemistry No. 1, 89～93 ·研究简报· 3-(4-β-D-吡喃阿洛糖苷苯基)-4-胺羰基-5- 甲氧羰基异噁唑衍生物的 合成及其镇静活性的研究 * 胡 翠 杨鸿均 李 颖 尹述凡 ( 四川大学化学学院 成都 610064) 摘要 4-(β -D-吡喃阿洛糖苷)-α-氯代苯甲醛肟与N-芳基马来酰亚胺在三乙胺作用下, 以甲醇为溶剂, 通过 1,3-偶极环加 成, 合成了一系列未见文献报道的 3-(4-β -D- 吡喃阿洛糖苷苯基)-4-胺羰基-5- 甲氧羰基异噁唑衍生物; 其结构经 1H NMR, IR, MS (HRMS)加以确证. 并对 4a～4h 和 5a 进行了药理活性筛选, 结果表明, 部分化合物具有良好的镇静活性. 其中, 化合物 4b (200 mg•kg－1), 4c (200 mg•kg－1), 4h (200 mg•kg－1), 与豆腐果苷相比较具有更强的活性. 关键词 豆腐果苷; 1,3-偶极环加成; 异噁唑; 合成 Synthesis and Calm Activity of 3-(4-β-D-Allopyranosyloxy-phenyl)-4- [(un)substituted anilinocarbonyl]-5-methoxycarbonyl-isoxazoline Derivatives Hu, Cui Yang, Hongjun Li, Ying Yin, Shufan* (Faculty of Chemistry, Sichuan University, Chengdu 610064) Abstract A series of new 3-(4-β -D-allopyranosyloxyphenyl)-4-[(un)substituted anilinocarbonyl]-5-meth- oxycarbonyl-isoxazoline derivatives have been synthesized by the condensation between 4-β -D-allopyranosy- loxy-α-chloro-benzaldehydeoxime and N-[(un)substituted phenyl]maleimides with triethylamine in the metha- nol through a 1,3-dipolar cycloaddition reaction. The structures of all the new compounds were established by 1 H NMR, IR, and MS (HRMS) techniques. The preliminary bioassay test of 4a～4h and 5a suggested that