中华医学超声杂志

应用化学 ›› 2010, Vol. 27 ›› Issue (02): 164-168.DOI: 10.3724/SP.J.1095.2010.90110

• 研究论文 • 上一篇    下一篇

含氟吡啶羧酸酯类化合物的合成及生物活性

郑辉1,刘运奎2,赵卿徐1,振元2*   

  1. (1.杭州师范大学材料与化学化工学院 杭州;2.浙江工业大学化学工程与材料学院 杭州 310014)
  • 收稿日期:2009-02-20 修回日期:2009-05-29 出版日期:2010-02-10 发布日期:2010-02-10
  • 通讯作者: 徐振元，男，教授; E-mail:chrc@zjut.edu.cn; 研究方向：绿色化学合成，新药创制
  • 基金资助:
    国家“九七三”计划(2003CB114400)长三角重大科技联合攻关(2004E60056)资助项目

Synthesis and Biological Activity of Novel Fluorine-Containing Pyridine-Heterocyclic Carboxylate Compounds

ZHENG Hui1, LIU Yun-Kui2, ZHAO Qing1, XU Zhen-Yuan2*   

  1. (1.Chemistry & Chemical Engineering,College of Material,Hangzhou Normal University,Hangzhou;
    2.College of Chemical Engineering & Materials,Zhejiang University of Technology,Hangzhou 310014)
  • Received:2009-02-20 Revised:2009-05-29 Published:2010-02-10 Online:2010-02-10

PDF

1364

被引次数

3 | 3

摘要：

为了寻找具有生物活性的新化合物，以氟乙酸甲酯、氰乙酰胺和甲酸乙酯为起始原料，经环合、氯化、水解、酰氯化等反应合成了含氟吡啶酰氯中间体，再与醇类和酚类反应合成了一系列含氟吡啶羧酸酯类化合物，总收率约38%。其结构经1 H NMR、13C NMR、IR、MS及元素分析测试技术确证。初步杀虫抑菌活性测试表明，部分化合物1e、1i、1j 和1k在500 mg/L浓度下，对淡色库蚊的杀死率在61.9%~100%之间，但对几种受试植物病菌的抑制活性很差。化合物1k活性最好，在500 mg/L时对粘虫(armyworm)和淡色库蚊(culexmosquito)的杀死率均为100%。初步构效关系分析表明，芳杂环酚的该类化合物有较好的活性，而脂肪醇的该类化合物无活性。

关键词: 含氟化合物，吡啶杂环，羧酸酯类，生物活性

Abstract:

In the search of bioactive compounds, a series of fluorine-substituted pyridine- heterocyclic carboxylate compounds were synthesized starting with methyl fluoroacetate, cyanacetamide, ethyl formic ester, alcoholic and phenolic compounds via ring closure, chlorination, hydrolyzation, acylchloriration and esterification reaction. The overall yield was about 38%. All compounds were characterized by 1H NMR, 13C NMR, IR, MS and elemental analysis. The preliminary bioassay results showed that some compounds 1e, 1i, 1j and 1k exhibited 61.9%-100% mortality against culex mosquito at 500 mg/L and little inhibition against several tested fungi. The compound 1k had better bioactivity and exhibited 100% mortality against armyworm and culex mosquito at 500 mg/L. Preliminary structure-activity relationship results revealed that the phenolic title compounds had good bioactivities while the alcoholic compounds do not.

Key words: fluorinated compound,pyridine heterocycle,carboxylate,bioactivity

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