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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (11): 1386-1391. 上一篇    下一篇

研究论文

含苯并噻唑基乳糖基胍的合成

田晓红a，曹玲华*,a,b   

  1. (a新疆大学化学化工学院 乌鲁木齐 830046)
    (b南开大学元素有机化学国家重点实验室 天津 300071)
  • 收稿日期:2006-09-06 修回日期:2007-04-03 发布日期:2007-10-20
  • 通讯作者: 曹玲华

Synthesis of Lactosylguanidines Linked with Benzothiazolyls

TIAN Xiao-Honga,CAO Ling-Hua*,a,b   

  1. (a College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046)
    (b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071)
  • Received:2006-09-06 Revised:2007-04-03 Published:2007-10-20
  • Contact: CAO Ling-Hua

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810

被引次数

7 | 1

2,3,6,2',3',4',6'-七-O-乙酰基-β-乳糖基异硫氰酸酯(1)分别与2-氨基-4/6-取代苯并噻唑2a～2e反应, 制得糖基硫脲3a～3e, 将其在HgCl2作用下与伯胺反应, 制得一系列新化合物N-烷基/芳基-N'-(4/6-取代-苯并噻唑-2-基)-N''-(2,3,6,2',3',4',6'-七-O-乙酰基-β-乳糖基)胍4～6. 然后, 在CH3ONa/CH3OH作用下, 脱乙酰基得含苯并噻唑基的乳糖基胍类化合物7～9. 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b-构型. 对代表性化合物的生物活性测试结果表明, 乳糖基胍类化合物对HIV-1蛋白酶、血管紧张素转化酶(ACE)的抑制活性较差.

关键词: 乳糖基异硫氰酸酯, 苯并噻唑, 乳糖基硫脲, 乳糖基胍

The reaction of 2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactosyl isothiocyanate (1) with 2-amino-4/6- substituted benzothiazoles 2a～2e gave lactosylthioureas 3a～3e, which were treated with amines in the presence of HgCl2 to afford a series of novel N-alkyl/aryl-N'-(4/6-substituted benzothiazol-2-yl)-N''-perace- tylated lactosylguanidines 4～6. Compounds 4～6 then reacted with the solution of CH3ONa/CH3OH, resulting in the formation of the deacetylated lactosylguanidines 7～9. The structures of the new compounds were established on the basis of IR, 1H NMR, mass spectral data and elemental analyses and all compounds were found to take the β-configuration. Bioassay indicates that these lactosylguanidines show little anti-HIV-1 PR activity and little anti-angiotensin converting enzyme activity.

Key words: benzothiazole, lactosylthiourea, lactosylguanidine, lactosyl isothiocyanate