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

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2a2e反应, 制得糖基硫脲3a3e, 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46. 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79. 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 2a2e gave lactosylthioureas 3a3e, 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 46. Compounds 46 then reacted with the solution of CH3ONa/CH3OH, resulting in the formation of the deacetylated lactosylguanidines 79. 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