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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (06): 1055-1060. 上一篇    下一篇

研究论文

3-O-乙酰基熊果酸3-乙酰基-2-[(未)取代苯基]-2,3-二氢-1,3, -噁二唑-5-甲酯的合成及其抗炎活性研究

杨定菊，李颖，尹述凡*   

  1. (四川大学化学学院 成都 610064)
  • 收稿日期:2007-04-27 修回日期:2007-11-28 发布日期:2008-06-26
  • 通讯作者: 尹述凡

Synthesis and Anti-inflammatory Activity of 3-Acetyl-2-[(un)substituted phenyl]-2,3-dihydro-1,3,4-oxadiazol-5-methyl 3-O-Acetylursolate

YANG Ding-Ju, LI Ying, YIN Shu-Fan*   

  1. (Faculty of Chemistry, Sichuan University, Chengdu 610064)
  • Received:2007-04-27 Revised:2007-11-28 Published:2008-06-26
  • Contact: YIN Shu-Fan

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熊果酸与氯乙酸乙酯反应制得熊果酸乙氧甲酰基甲酯(2), 2与水合肼反应得到熊果酸甲酰肼甲酯(3), 3与羰基化合物反应得到一系列酰腙4a～4g, 再将4a～4g与乙酸酐作用, 环合得到3-O-乙酰基熊果酸3-乙酰基-2-[(未)取代苯基]-2,3-二氢-1,3,4-噁二唑-5-甲酯(5a～5g). 15个新化合物均未见文献报道, 其结构经1H NMR, IR, MS加以确证, 并进行了药理结果筛选. 结果表明, 部分化合物具有良好的抗炎活性. 其中, 化合物5a (40 mg•kg－1), 5d (40 mg•kg－1), 5g (40 mg•kg－1)与熊果酸相比, 具有更强的疗效.

关键词: 熊果酸, 1,3,4-噁二唑, 抗炎活性, 合成

Ethoxycarbonylmethyl ursolate obtained by a reaction of ursolic acid with ClCH2COOC2H5 reacted with hydrazine hydrate to give hydrazi-nocarbonylmethyl ursolate (3). Reaction of the hydrazide 3 with keto compounds give the corresponding hydrazones 4a～4g, which could be readily convered to 3-acetyl-2-[(un)substituted phenyl]-2,3-dihydro-1,3,4-oxadiazol-5-methyl 3-O-acetylursolate (5a～5g) in good yields by treatment with Ac2O. The structures of new products were characterized by 1H NMR, IR and MS spectra. By the preliminary bio-assay test some of such compounds show good anti-inflammatory activity. For example, compounds 5a (40 mg•kg－1), 5d (40 mg•kg－1) and 5g (40 mg•kg－1) were better than the parent ursolic acid.

Key words: 1,3,4-oxadiazol, synthesis, anti-inflammatory activity, ursolic acid