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Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (02): 222-228. Previous Articles     Next Articles

Original Articles

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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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