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化学学报
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化学学报 ›› 2007, Vol. 65 ›› Issue (4): 349-354. 上一篇    下一篇

研究论文

胍基木吡喃糖苷的合成及其抗HIV蛋白酶活性

曹玲华*,1,2, 连召斌1   

  1. (1新疆大学化学化工学院 乌鲁木齐 830046)
    (2南开大学元素有机化学国家重点实验室 天津 300071)
  • 投稿日期:2006-08-22 修回日期:2006-09-20 发布日期:2007-02-28
  • 通讯作者: 曹玲华

Synthesis of Guanidinoxylopyranosides and Their Anti-HIV PR Activity

CAO Ling-Hua*,1,2; LIAN Zhao-Bin1   

  1. (1 College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046)
    (2 State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071)
  • Received:2006-08-22 Revised:2006-09-20 Published:2007-02-28
  • Contact: CAO Ling-Hua

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被引次数

10 | 2

2,3,4-三-O-乙酰基-b-D-木吡喃糖基异硫氰酸酯1与2-氨基-4/6-取代-苯并噻唑2a～2e反应, 生成糖基硫脲衍生物3a～3e, 再在伯胺存在下经氯化汞脱硫, 得到一系列新的胍基木吡喃糖苷类化合物4a～4e, 5a～5e, 6a～6e, 7a～7e, 所有新化合物的结构均经IR, 1H NMR, MS谱和元素分析证实, 所得产物均为β-构型. 生物活性测试结果表明, 化合物4c, 5b, 6b～6d, 7b等对HIV-1蛋白酶表现出了较高的抑制活性.

关键词: 木吡喃糖基异硫氰酸酯, 木吡喃糖基硫脲, 胍基木吡喃糖苷, 生物活性

The reaction of 2,3,4-tri-O-acetyl-b-D-xylopyranosyl isothiocyanate 1 and 2-amino-4/6-substituted benzothiazoles 2a～2e gave xylopyranosylthioureas 3a～3e, which then reacted with alkyl/aryl amine in the presence of HgCl2 to afford a series of new guanidinoxylopyranosides (4a～4e, 5a～5e, 6a～6e and 7a～7e). The structures of the new compounds were established on the basis of elemental analyses, IR, 1H NMR and mass spectral data and all compounds took b-configuration. The biological activities of these compounds have been evaluated. Compounds 4c, 5b, 6b～6d and 7b showed anti-HIV-1 PR activity.

Key words: xylopyranosyl isothiocyanate, xylopyranosylthiourea, guanidinoxylopyranoside, anti-HIV-1 PR activity