引用本文:
郑辉, 刘运奎, 赵卿, 徐振元. 含氟吡啶羧酸酯类化合物的合成及生物活性[J]. 应用化学,
2010, 27(2): 164-168.
doi:
10.3724/SP.J.1095.2010.90164
Citation: ZHENG Hui, LIU Yun-Kui, ZHAO Qing, XU Zhen-Yuan. Synthesis and Biological Activity of Fluorine-Substituted Pyridine-Heterocyclic Carboxylate Compounds[J]. Chinese Journal of Applied Chemistry, 2010, 27(2): 164-168. doi: 10.3724/SP.J.1095.2010.90164
Citation: ZHENG Hui, LIU Yun-Kui, ZHAO Qing, XU Zhen-Yuan. Synthesis and Biological Activity of Fluorine-Substituted Pyridine-Heterocyclic Carboxylate Compounds[J]. Chinese Journal of Applied Chemistry, 2010, 27(2): 164-168. doi: 10.3724/SP.J.1095.2010.90164
含氟吡啶羧酸酯类化合物的合成及生物活性
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1H 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500mg/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500mg/L时对粘虫(armyworm)和淡色库蚊(culex mosquito)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。
English
Synthesis and Biological Activity of Fluorine-Substituted Pyridine-Heterocyclic Carboxylate Compounds
Abstract:
In the search of bioactive compounds,a series of fluorine-substituted pyridine-heterocyclic carboxylate compounds were synthesized with methyl fluoroacetate,cyanacetamide,ethyl formic ester,alcoholic and phenolic compounds via ring closure,chlorination,hydrolyzation,acylchloriration and esterification reactions. The overall yield was about 38%. All compounds were characterized by 1H NMR,13C NMR,IR,MS and elemental analysis. The preliminary bioassay results show that 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. Compound 1k had better bioactivity and exhibited 100% mortality against armyworm and culex mosquito at 500 mg/L. The preliminary structure-activity relationship results reveal that the title phenolic compounds have good bioactivities while the alcoholic compounds do not.
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Key words:
- fluorinated compound
- / pyridine heterocycle
- / carboxylate
- / bioactivity
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