Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (11): 1386-1391. Previous Articles     Next Articles

Original Articles



  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

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