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有机化学 ›› 2008, Vol. 28 ›› Issue (2): 348-352. 上一篇    下一篇

研究简报

3-(4-β-D-吡喃阿洛糖苷-苯基)-4-芳基-5-芳基-1,2,4-噁二唑啉的合成及其镇静活性的研究

刘敏，李颖，尹述凡*   

  1. (四川大学化学学院 成都 610064)
  • 收稿日期:2007-04-12 修回日期:2007-06-27 发布日期:2008-02-01
  • 通讯作者: 尹述凡

Synthesis and Calm Activity of 3-(4-β-D-Allopyranosyloxyphenyl)-4- aryl-5-aryl-1,2,4-oxadiazoline

LIU Min,LI Ying,YIN Shu-Fan*   

  1. (Faculty of Chemistry, Sichuan University, Chengdu 610064)
  • Received:2007-04-12 Revised:2007-06-27 Published:2008-02-01
  • Contact: YIN Shu-Fan

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以豆腐果苷为原料, 与盐酸羟胺缩合反应生成4-β-D-吡喃阿洛糖苷-苯甲醛肟(2), 2与次氯酸叔丁酯发生取代反应生成4-β-D-吡喃阿洛糖苷-α-氯苯甲醛肟(3); 再将3与Schiff碱通过1,3-偶极环加成生成一系列3-(4-β-D-吡喃阿洛糖苷-苯基)-4-芳基-5-芳基-1,2,4-噁二唑啉(5a～5h). 3和 5a～5h共9个化合物均未见文献报道, 其结构经1H NMR, IR和MS (HRMS)加以确认, 并对5a～5h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5g (200, 100 mg•kg－1)和5h (200, 100 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, 4-β-D-吡喃阿洛糖苷-α-氯苯甲醛肟, 1,3-偶极环加成, 合成, 1,2,4-噁二唑啉

Using helicid as a starting material, 4-β-D-allopyranosyloxy-benzaldehydeoxime (2) has been synthesized by the condensation reaction with hydroxyamine hydrochloride. Novel 4-β-D-allopyranosyloxy-α- chloro-benzaldehydeoxime (3) was synthesized by substitution reaction of 2 with t-BuOCl, and novel 3-(4-β-D-allopyranosyloxyphenyl)-4-aryl-5-aryl-1,2,4-oxadiazoline derivatives (5a～5h) have been synthesized by 1,3-dipolar cycloaddition reaction of 3 with Schiff bases 4a～4h. The new compounds 3 and 5a～5h were established by 1H NMR, IR, and MS (HRMS) spectra. The preliminary bioassay test of 5a～5h showed that some of such compounds have good calm activity. For example, com-pounds 5g (200, 100 mg•kg－1) and 5h (200, 100 mg•kg－1) were better than the parent helicid.

Key words: 4-β-D-allopyranosyloxy-α-chloro-benzaldehydeoxime, helicid, 1,3-dipolar cycloaddition, synthesis, 1,2,4-oxadiazoline