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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (05): 899-902. 上一篇    下一篇

研究简报

1-烃基-2-(4-β-D-吡喃阿洛糖苷-苯基)-苯并咪唑类化合物的合成及其镇静活性的研究

杨鸿均，胡翠，李颖，尹述凡*   

  1. (四川大学化学学院 成都 610064)
  • 收稿日期:2007-08-18 修回日期:2007-11-09 发布日期:2008-05-20
  • 通讯作者: 尹述凡

Synthesis of Calm Activity 1-Alkyl-2-(4-β-D-allopyranosyloxyphenyl)- benzimidazole Derivatives

YANG Hong-Jun,HU Cui,LI Ying,YIN Shu-Fan*   

  1. (Faculty of Chemistry, Sichuan University, Chengdu 610064)
  • Received:2007-08-18 Revised:2007-11-09 Published:2008-05-20
  • Contact: YIN Shu-Fan

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以豆腐果苷为原料, 在冰醋酸催化下和邻苯二胺缩合生成中间体2-(4-β-D-吡喃阿洛糖苷-苯基)-苯并咪唑(2), 2与卤代烃在K2CO3作用下以乙醇为溶剂合成了一系列1-烃基-2-(4-β-D-吡喃阿洛糖苷-苯基)-苯并咪唑类化合物3a～3h. 新化合物2和3a～3h的结构经1H NMR, IR和MS (HRMS)确认, 并对2和3a～3h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2 (100 mg•kg－1), 3f (100 mg•kg－1)与豆腐果苷相比较具有更强的药理活性.

关键词: 豆腐果苷, 苯并咪唑, 1,2-苯二胺, 合成

2-(4-β-D-Allopyranosyloxyphenyl)benzimidazole (2) has been synthesized by the condensation of helicid with 1,2-phenylenediamine using CH3COOH as a catalyst. 1-Alkyl-2-(4-β-D-allopyranosyloxy- phenyl)benzimidazole derivatives 3a～3h were synthesized by the reaction of 2 with alkyl halides and K2CO3 in ethanol. The structures of all new compounds 2 and 3a～3h were characterized by 1H NMR, IR and MS (HRMS) spectra. The preliminary bioassay test of 2 and 3a～3h showed that some of such compounds have good calm activity. For example, compounds 2 (100 mg•kg－1) and 3f (100 mg•kg－1) were better than the parent helicid.

Key words: benzimidazole, 1,2-phenylenediamine, synthesis, helicid