有机化学 ›› 2011, Vol. 31 ›› Issue (01): 110-114. 上一篇    下一篇

研究简报

2-(4-β-D-吡喃阿洛糖苷-苯基)-5-取代芳基-1,3,4-噁二唑的合成及镇静活性研究

李家林,樊波,罗华玲,李颖,尹述凡   

  1. (四川大学化学学院 成都 610064)
  • 收稿日期:2010-03-16 修回日期:2010-06-20 发布日期:2010-08-10
  • 通讯作者: 尹述凡 E-mail:chuandayouji217@163.com;;

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

LI Jia-Lin, FAN Bo, LUO Hua-Ling, LI Ying, YIN Shu-Fan   

  1. (Faculty of Chemistry, Sichuan University, Chengdu 610064)
  • Received:2010-03-16 Revised:2010-06-20 Published:2010-08-10

以豆腐果苷为原料, 与取代苯甲酰肼反应生成中间体4-β-D-吡喃阿洛糖苷-苯甲醛取代苯甲酰腙(2a2g), 在溴作催化剂的条件下发生关环反应, 合成了一系列豆腐果苷类似物3a3g. 所有化合物结构经IR, 1H NMR以及MS谱得以证实. 初步药理实验结果表明, 化合物3a, 3c, 3f与豆腐果苷相比有更好的镇静活性.

关键词: 豆腐果苷, 镇静活性, 1,3,4-噁二唑, 合成, 环化

A series of novel helicid derivatives containing 1,3,4-oxadiazole 3a3g were successfully synthesized from the intermediates aryl-3-carbonyl (4-β-D-allopyranoside-yl)-benzaldehyde hydrazone derivatives (2a2g), which prepared starting from helicid. The new compounds were characterized by 1H NMR, IR and HR-MS spectra. The sedative-hypnotic activities of the target compounds 3a3g were evaluated by testing the spontaneous locomotor activity in mice. All of the derivatives produced moderate to high activities. In particularly, compound 3c presented the most potent sedative-hypnotic effect in comparison to the other derivatives, and compounds 3a and 3f also showed potent activities.

Key words: helicid, calm activity, 1,3,4-oxadiazole, synthesis, cyclization