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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (10): 1403-1408. 上一篇    下一篇

研究论文

乙酰水杨酰对羟基桂皮酸与呋咱氮氧化物和硝酸酯偶联物的合成及其抗血栓作用

周洲a，蒋丽媛a，张奕华*,a，季晖b，孙易b，彭司勋a   

  1. (a中国药科大学新药研究中心 南京 210009)
    (b中国药科大学药理学教研室 南京 210009)
  • 收稿日期:2005-12-06 修回日期:2006-04-12 发布日期:2006-09-19
  • 通讯作者: 张奕华

Synthesis and Antithrombotic Activity of Acetylsalicyl p-Coumaric Acid Coupled with Furoxans and Nitrates

ZHOU Zhoua,JIANG Li-Yuana,ZHANG Yi-Hua*,a
JI Huib,SUN Yib,PENG Si-Xuna   

  1. (a Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009)
    (b Department of Pharmacology, China Pharmaceutical University, Nanjing 210009)
  • Received:2005-12-06 Revised:2006-04-12 Published:2006-09-19
  • Contact: ZHANG Yi-Hua

PDF

1255

被引次数

11

对羟基桂皮酸酚羟基经保护后与相应的羟基呋咱氮氧化物酯化, 酯化物脱保护, 再与阿司匹林缩合得II1～II3; 对羟基桂皮酸与相应二溴烷烃作用, 再经阿司匹林酯化, 得到的溴代烷基酯与硝酸银反应得II4～II7; 酚羟基保护的对羟基桂皮酸与异山梨醇单硝酸酯酯化, 脱保护后与阿司匹林缩合得II8. 目标物II1～II8均经MS, IR, 1H NMR和元素分析确证, 并通过大小鼠体内外抗血栓活性初筛, 结果表明, 多数目标物显示与阿司匹林相当的抗血栓活性, II6活性优于阿司匹林.

关键词: 乙酰水杨酰对羟基桂皮酸, 抗血栓活性, 呋咱氮氧化物, 合成, 阿司匹林

The protected p-coumaric acid was esterified with corresponding hydroxyfuroxan, and the resulted ester was deprotected and condensed with aspirin to give II1～II3, respectively. Treatment of p-coumaric acid with dibromoalkane, followed by esterification with aspirin offered acetylsalicyl p-coumaric acid bromoalkyl ester, and then reacted with silver nitrate to give II4～II7, respectively. II8 was obtained by esterification of the protected p-coumaric acid with isosorbide mononitrate, subsequent deprotection and condensation with aspirin. II1～II8 were identified by MS, IR, 1H NMR spectra and elemental analysis, and screened for in vitro and in vivo thrombosis inhibitory activities in mice and rats. Most of tested compounds are comparable to aspirin in antithrombotic activity, and II6 is more potent than aspirin.

Key words: furoxan, antithrombotic activity, aspirin, synthesis, acetylsalicyl p-coumaric acid