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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (07): 1273-1277. 上一篇    下一篇

研究简报

4-烃基-3-氰基-双环笼状磷酸酯类化合物的合成及生物活性研究

吴有斌; 周 巍; 巨修练*   

  1. (武汉工程大学化工与制药学院 绿色化工过程教育部重点实验室
    湖北省新型反应器与绿色化学工艺重点实验室 武汉 430073)
  • 收稿日期:2007-10-07 修回日期:2008-02-18 发布日期:2008-07-28
  • 通讯作者: 巨修练

Synthesis and Bioactivity of 4-Alkyl-3-cyano-caged Bicyclic-phosphates

WU, You-Bin ; ZHOU, Wei; JU, Xiu-Lian*   

  1. (Key Laboratory for Green Chemical Process of Ministry of Education, Hubei Key Laboratory of Novel Chemical Reactor and
    Green Chemical Technology, School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430073)

  • Received:2007-10-07 Revised:2008-02-18 Published:2008-07-28
  • Contact: JU, Xiu-Lian

PDF

639

被引次数

11

以2-烃基-2-羟甲基-1,3-丙二醇为原料, 经保护两个羟基, PCC氧化, 引入氰基, 脱保护后与POCl3或PSCl3环合, 成功合成了14个4-烃基-3-氰基双环笼状磷酸酯类化合物, 目标化合物的结构通过1H NMR, MS和元素分析进行了表征. 采用放射性配体受体结合实验, 测定了14个化合物抑制[3H]EBOB [4’-ethynyl-4-n-propylbicycloorthobenzoate]与家蝇及大鼠GABA受体的结合活性. 结果表明部分化合物在10－5 mol/L具有较好的抑制活性, 且在大鼠与家蝇GABA受体之间具有一定选择性.

关键词: GABA受体, 放射性配体受体结合实验, 生物活性, 双环笼状磷酸酯

Fourteen 4-alkyl-3-cyano-caged bicyclic-phosphates were synthesized from 2-alkyl-2-hy- droxymethyl-1,3-propanediols via protection of the two hydroxyl groups, oxidation of the other hydroxyl group with PCC, introduction of the CN group, deprotection and cyclization with POCl3 or PSCl3. All target compounds were confirmed by 1H NMR, MS spectra and elemental analysis. In addition, the 14 compounds were examined for their inhibition of [3H]EBOB [4’-ethynyl-4-n-propylbicycloorthobenzoate] binding to housefly and rat GABA receptors and the results show that some of these compounds have inhibiting activity and selectivity between the rat and housefly GABA receptors at 10－5 mol/L.

Key words: GABA receptor, radioligand receptor binding assay, bioactivity, caged bicyclic-phosphate