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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
引用本文:杨定菊,李颖,尹述凡. 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[J]. 有机化学, 2008, 28(6): 1055-1060
作者姓名:杨定菊  李颖  尹述凡
作者单位:四川大学化学学院,成都,610064
摘    要: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4a4g, 再将4a4g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(5a5g). 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  合成  抗炎活性
收稿时间:2007-04-27
修稿时间:2007-04-27

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. Synthesis and Anti-inflammatory Activity of 3-Acetyl-2-[(un)substituted phenyl]-2,3-dihydro-1,3,4-oxadiazol-5-methyl 3-O-Acetylursolate[J]. Chinese Journal of Organic Chemistry, 2008, 28(6): 1055-1060
Authors:YANG  Ding-Ju  LI  Ying  YIN  Shu-Fan
Affiliation:(Faculty of Chemistry, Sichuan University, Chengdu 610064)
Abstract: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 4a4g, which could be readily convered to 3-acetyl-2-[(un)substituted phenyl]-2,3-dihydro-1,3,4-oxadiazol-5-methyl 3-O-acetylursolate (5a5g) 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.
Keywords:ursolic acid  1,3,4-oxadiazol  synthesis  anti-inflammatory activity
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