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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (01): 89-93. 上一篇    下一篇

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*   

  1. (四川大学化学学院 成都 610064)
  • 收稿日期:2008-12-06 修回日期:1900-01-01 发布日期:2009-01-20
  • 通讯作者: 尹述凡

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*   

  1. (Faculty of Chemistry, Sichuan University, Chengdu 610064)
  • Received:2008-12-06 Revised:1900-01-01 Published:2009-01-20
  • Contact: Yin, Shufan

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988

被引次数

3 | 6

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: 合成, 豆腐果苷, 1,3-偶极环加成, 异噁唑

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 1H NMR, IR, and MS (HRMS) techniques. The preliminary bioassay test of 4a～4h and 5a suggested that some of these compounds should show good calm activity. For example, compounds 4b (200 mg•kg－1), 4c (200 mg•kg－1) and 4h (200 mg•kg－1) were better than the parent helicid.

Key words: 1,3-dipolar cycloaddition, isoxazoline, synthes, helicid