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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (05): 660-666. 上一篇    下一篇

研究论文

β-D-葡萄糖基硫脲合成及生物活性研究

王小明1，朱涛2，郑良玉3，李耀先1，张锁秦*,1，白杰1   

  1. (1吉林大学化学学院 长春 130023)
    (2吉林大学超分子结构与材料教育部重点实验室 长春 130012)
    (3吉林大学分子酶学工程教育部重点实验室 长春 130023)
  • 收稿日期:2005-05-11 修回日期:2005-11-16 发布日期:2006-04-28
  • 通讯作者: 张锁秦

Synthesis of β-D-Glucopyranosyl Thiourea and Biological Activity

WANG Xiao-Ming1,ZHU Tao2,ZHENG Li-ang-Yu3,LI Yao-Xian1
ZHANG Suo-Qin*,1,BAI Jie1   

  1. (1 College of Chemistry, Jilin University, Changchun 130023)
    (2 Key Laboratory for Supramolecular Structure and Materials of Ministry of Education, Jilin University, Changchun 130012)
    (3 Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, Jilin University, Changchun 130023)
  • Received:2005-05-11 Revised:2005-11-16 Published:2006-04-28
  • Contact: ZHANG Suo-Qin

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从1-溴-2,3,4,6-四乙酰化-β-D-吡喃葡萄糖I出发, 经异硫氰酸酯化反应, 合成了2,3,4,6-四乙酰化-β-D-吡喃糖基硫脲化合物IV, 再经脱乙酰化得到V. 将乙酰化糖基异硫氰酸酯的合成从文献的60%提高到80%. 所得化合物经元素分析, IR, MS, 1H NMR和 13C NMR谱学分析确定了结构, 并对产物进行了初步的除草活性测试.

关键词: 糖基硫脲, 合成, 生物活性

2,3,4,6-Tetra-acetyl-β-D-glucopyranosyl thioureas IV were synthesized by the reaction aniline with 2,3,4,6-tetra-acetyl-β-D-glucopyranosyl isothiocyanate generated from 1-bromo-2,3,4,6-tetra-acetyl-α- D-glucopyranuronate and KSCN in reflux acetonitrile. In the synthesis of acetyl-β-D-glucopyranosyl isothiocyanate, the yield was raised from 60% to 80%. The structures of the compounds were confirmed by IR, MS, NMR spectra and elemental analysis. The preliminary biological tests indicate that some compouds of IV and V show good herbicidal activity.

Key words: synthesis, biological activity, glucosyl thiourea