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有机化学 ›› 2007, Vol. 27 ›› Issue (9): 1150-1154. 上一篇    下一篇

研究简报

2-(4-β-D-吡喃阿洛糖苷-苯基)-4-芳基-2,3-二氢-1,5-苯并硫氮杂的合成及镇静活性的研究

樊波，李家林，李颖，尹述凡*   

  1. (四川大学化学学院 成都 610064)
  • 收稿日期:2006-11-01 修回日期:2007-01-24 发布日期:2007-08-30
  • 通讯作者: 尹述凡

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

FAN Bo,LI Jia-Lin,LI Ying,YIN Shu-Fan*   

  1. (Faculty of Chemistry, Sichuan University, Chengdu 610064)
  • Received:2006-11-01 Revised:2007-01-24 Published:2007-08-30
  • Contact: YIN Shu-Fan

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以豆腐果苷为原料, 与4-取代苯乙酮发生Claisen-Schimidt反应, 得到一系列E-4-β-D-吡喃阿洛糖苷-苯乙烯基- 4-取代苯酮衍生物1a～1e, 再将1a～1e与邻氨基苯硫酚发生1,4-Michael反应, 得到2-(4-β-D-吡喃阿洛糖苷-苯基)-4-芳基-2,3-二氢-1,5-苯并硫氮杂衍生物2a～2e, 以上化合物均未见文献报道, 其结构经1H NMR, IR, MS加以确证, 并对2a～2e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2a (200 mg•kg－1), 2b (200 mg•kg－1), 2c (200 mg•kg－1), 2d (200 mg•kg－1), 2e (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, 合成, Claisen-Schimidt反应, 苯并硫氮杂, 1,4-Michael反应, 镇静活性

Using helicid as starting material, novel E-(4-β-D-allopyranosyloxyphenyl)-1-(4-substituted phenyl)propenone derivatives (1a～1e) have been synthesized by Claisen-Schimidt reaction with 4-substituted hypnone. 2-(4-β-D-Allopyranosyloxyphenyl)-4-aryl-2,3-dihydro-1,5-benzothiazepine derivatives (2a～2e) have been synthesized by 1,4-Michael reaction with 1a～1e. The new compounds were established by 1H NMR, IR and MS spectra. The pre-liminary bioassay test of 2a～2e suggested that some of them should show good calm ac-tivity. For example, compounds 2a (200 mg•kg－1), 2b (200 mg•kg－1), 2c (200 mg•kg－1), 2d (200 mg•kg－1) and 2e (200 mg•kg－1) were better than the parent helicid.

Key words: 1,4-Michael reaction, 1,5-benzothiazepine, calm activity, Claisen-Schimidt reaction, synthesis, helicid