高等学校化学学报

高等学校化学学报

• 研究论文 • 上一篇    下一篇

新型胍基葡萄糖苷的合成及生物活性

连召斌1, 田晓红1, 曹玲华1,2   

    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:2006-07-31 修回日期:1900-01-01 出版日期:2007-07-10 发布日期:2007-07-10
  • 通讯作者: 曹玲华

Synthesis and Biological Activities of Novel Guanidinoglucosides

LIAN Zhao-Bin1, TIAN Xiao-Hong1, CAO Ling-Hua1,2*   

    1. College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China;
    2. State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China
  • Received:2006-07-31 Revised:1900-01-01 Online:2007-07-10 Published:2007-07-10
  • Contact: CAO Ling-Hua

PDF (PC)

被引次数

12

摘要：

将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-4/6-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, 得到一系列新的多乙酰基胍基糖苷类化合物(4a~4d, 5a~5d, 6a~6d, 7a~7d), 糖基的保护基团在甲醇钠/甲醇条件下脱除. 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, 6c, 8b, 8c等对HIV-1蛋白酶表现出了较高的抑制活性; 化合物7c具有抗流感乙型病毒活性; 化合物5e, 7c, 7d等对血管紧张素转化酶具有抑制活性.

关键词: 糖基异硫氰酸酯, 糖基硫脲, 胍基糖苷, 生物活性

Abstract:

The reaction of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 1 with 2-amino-4/6-substituted benzothiazoles 2a—2b gave glucosylthioureas(3a—3b), which then reacted with alkyl/aryl amine in the presence of HgCl2 to afford a series of new poly-acetyl guanidinoglucosides(4a—4d, 5a—5d, 6a—6d and 7a—7d). Deacetylation of glycosyl was carried in the CH3OH/CH3ONa solution. 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 β-configuration. The biological activities of these compounds have been evaluated. Compounds 4c, 6c, 8b and 8c showed anti-HIV-1 PR activity, compound 7c showed anti-influenza activity and compounds 5e, 7c and 7d showed inhibitory activity against angiotensin-converting enzyme(ACE) activity.

Key words: Glucopyranosyl isothiocyanate, Glucosylthiourea, Guanidinoglucoside, Biological activity

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