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β-D-葡萄糖基硫脲合成及生物活性研究

Synthesis of β-D-Glucopyranosyl Thiourea and Biological Activity

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【作者】 王小明朱涛郑良玉李耀先张锁秦白杰

【Author】 WANG, Xiao-Ming a ZHU, Tao b ZHENG, Liang-Yu c LI, Yao-Xian a ZHANG, Suo-Qin*,a BAI, Jiea (a College of Chemistry, Jilin University, Changchun 130023) (b Key Laboratory for Supramolecular Structure and Materials of Ministry of Education, Jilin University, Changchun 130012) (c Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, Jilin University, Changchun 130023)

【机构】 吉林大学化学学院吉林大学超分子结构与材料教育部重点实验室吉林大学分子酶学工程教育部重点实验室吉林大学化学学院 长春130023长春130012长春130023

【摘要】 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,1HNMR和13CNMR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.

【Abstract】 2,3,4,6-Tetra-acetyl-β-D-glucopyranosyl thioureas IV were synthesized by the reaction of 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 isothi- ocyanate, 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.

【关键词】 糖基硫脲合成生物活性
【Key words】 glucosyl thioureasynthesisbiological activity
  • 【文献出处】 有机化学 ,Chinese Journal of Organic Chemistry , 编辑部邮箱 ,2006年05期
  • 【分类号】TQ463.2
  • 【被引频次】26
  • 【下载频次】444
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