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有机化学 ›› 2005, Vol. 25 ›› Issue (9): 1066-1070. 上一篇    下一篇

研究论文

N-烷基/芳基-N'-(4-芳基噻唑-2-基)-N"-糖基胍的合成及生物活性研究

史合方1，曹玲华*,1,2   

  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)
  • 收稿日期:2004-09-06 修回日期:2005-03-26 发布日期:2005-08-24
  • 通讯作者: 曹玲华

Synthesis and Biological Activity of N-Alkyl/aryl-N'-(4-arylthiazol-2-yl)- N''-glycosyl Guanidines

SHI He-Fang1,CAO Ling-Hua*,1,2   

  1. (1 College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046)
    (2 State Key Laboratory of Elemento-Organic Chemistry, Nankai Univer-sity, Tianjin 300071)
  • Received:2004-09-06 Revised:2005-03-26 Published:2005-08-24
  • Contact: CAO Ling-Hua

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2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基异硫氰酸酯(1)与2-氨基-4-取代苯基噻唑(2a～2b)反应, 生成糖基硫脲衍生物3a～3b, 再在伯胺存在下经氯化汞脱硫, 得到一系列新的N-烷基/芳基-N'-(4-芳基噻唑-2-基)-N"-糖基胍类化合物(4a～4e, 5a～5e). 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4b和5d对HIV-1 PR表现出了较高的抑制活性.

关键词: 糖基异硫氰酸酯, 糖基硫脲, 糖基胍, 生物活性

The reaction of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (1) and 2-amino-4- arylthiazoles (2a～2b) gave glucosylthioureas 3a～3b, which then reacted with alkyl/aryl amine in the presence of HgCl2 to afford a series of new N-alkyl/aryl-N'-(4-arylthiazol-2-yl)-N''-glucosyl guanidines (4a～4e and 5a～5e). The structures of the new compounds were established on the basis of IR, 1H NMR and MS spectra and all compounds took β-configuration. The anti-HIV and antibacterial activities of these compounds have been evaluated. Compounds 4b and 5d showed anti-HIV activity.

Key words: glucosylthiourea, glucosyl isothiocyanate, guanidinoglucoside, biological activity