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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (02): 222-228. 上一篇    下一篇

研究论文

N-苄氧甲酰基(苯)丙氨酸取代苯基酯的合成及生物活性测定

唐子龙* ; 许栋梁 ; 刘汉文*; 欧晓明 ; 谭风姣   

  1. (a湖南科技大学化学化工学院 分子构效关系湖南省高校重点实验室 湘潭 411201)
    (b湖南化工研究院 国家农药创制工程技术研究中心 长沙 410007)
  • 收稿日期:2008-04-16 修回日期:2008-07-17 发布日期:2009-02-20
  • 通讯作者: 唐子龙;刘汉文

Synthesis and Bioactivity Studies on N-Benzyloxycarbonyl Alanine (Phenylalanine) Substituted-phenyl Esters

Tang, Zilong*; Xu, Dongliang; Liu, Hanwen* ;
Ou, Xiaoming; Tan, Fengjiao
  

  1. (a Hunan Provincial University Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering,
    Hunan University of Science and Technology, Xiangtan 411201)
    (b National Engineering Research Center of Agrochemicals, Hunan Research Institute of
    Chemical Industry, Changsha 410007)
  • Received:2008-04-16 Revised:2008-07-17 Published:2009-02-20
  • Contact: Tang, Zilong;Liu, Hanwen

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1349

被引次数

8 | 1

采用N,N’-二环已基酰二胺(DCC)和吡啶, 以及DCC和4-(N,N-二甲氨基)吡啶(DMAP)分别形成的脱水缩合体系, N-苄氧甲酰基氨基酸和酚发生缩合反应生成了一系列结构新颖的N-苄氧甲酰基(苯)丙氨酸取代苯基酯. 在DCC/DMAP体系中的反应产率大于在DCC/吡啶中的产率. 用1H NMR, 13C NMR, IR, MS和元素分析对目标化合物的结构进行了表征. 对合成的目标化合物进行了初步的生物活性测试, 结果表明目标化合物具有一定的杀菌活性和杀虫活性, 杀菌活性高于杀虫活性. DL-丙氨酸芳基酯比相应的L-丙氨酸芳基酯的杀蚜虫活性要高.

关键词: 生物活性, 丙氨酸, 苯丙氨酸, 合成, 氨基酸芳基酯, 氨基甲酸酯

A series of novel N-benzyloxycarbonyl alanine (phenylalanine) substituted-phenyl esters were synthesized by condensation reactions of N-Cbz-alanine (phenylalanine) with substituted phenols in the presence of N,N’-dicyclohexylcarbodimide (DCC) and pyridine, or DCC and 4-dimethylaminopyridine (DMAP). The yields of the reactions in the presence of DCC and DMAP were higher than those in DCC and pyridine. The target products were characterized by 1H NMR, 13C NMR, IR, MS techniques and elemental analysis. A preliminary bioactivity test of the target products was performed, and the results showed that they exhibited moderate fungicidal activity and insecticidal activity, with the former being higher than the latter.

Key words: phenylalanine, alanine, bioactivity, amino acid aryl ester, synthesis, carbamate