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6-溴-1-异丙烯基-1H-咪唑[4,5b]吡啶-2-酮酰胺衍生物的合成及其抑菌活性研究
侯 朝,魏少鹏,姬志勤
作者单位
侯 朝 西北农林科技大学 植物保护学院 
魏少鹏 西北农林科技大学 植物保护学院 
姬志勤 西北农林科技大学 植物保护学院 
摘要:
【目的】研究6-溴-1-异丙烯基-1H-咪唑[4,5b]吡啶-2-酮酰胺衍生物抑制真菌活性的构效关系,为病原菌的防治提供参考依据。【方法】以5-溴-2,3-二氨基吡啶为原料,经乙酰乙酸乙酯环化制得中间体化合物6-溴-1-异丙烯基-1H-咪唑[4,5b]吡啶-2-酮,再按照目标化合物合成路线设计合成6-溴-1-异丙烯基-1H-咪唑[4,5b]吡啶-2-酮酰胺衍生物。通过核磁共振、质谱以及元素分析对目标化合物进行结构表征。以嘧菌酯为对照,采用菌丝生长速率法测定目标化合物对小麦赤霉病菌(Fusarium graminearum)、玉米弯孢霉病菌(Curvularia lunata)、棉花枯萎病菌(Fusarium oxysporumf.sp.vasinfectum)、茄子黄萎病菌(Verticillium dahlia)、西瓜枯萎病菌(Fusarium oxysporum)和苹果炭疽病菌(Colletotrichum gloeosporioides)的抑菌活性。【结果】合成了17个6-溴-1-异丙烯基-1H-咪唑[4,5b]吡啶-2-酮酰胺衍生物,其中脂肪羧酸酰胺衍生物10个(B01-B10),芳香羧酸酰胺衍生物6个(B11-B16),杂环羧酸酰胺衍生物1个(B17)。抑菌活性测定结果表明,17个目标化合物对供试病原真菌均有一定的抑菌活性,其中化合物B01,B03-B06和B13在100 μg/mL质量浓度下对部分供试病原真菌菌丝生长有明显的抑制作用,尤以化合物B06的抑菌活性最为突出,抑制率均可达到70%以上,其对6种供试植物病原真菌的EC50值分别为8.23,49.32,21.45,24.87,36.40和28.65 μg/mL,均高于对照药剂嘧菌酯。【结论】6-溴-1-异丙烯基-1H-咪唑[4,5b]吡啶-2-酮衍生物对6种供试病原真菌均具有一定的抑制活性,该类化合物的结构具有进一步改造研究的价值。
关键词:  6-溴-1-异丙烯基-1H咪唑[4,5b]吡啶-2-酮  酰胺衍生物  抑菌活性
DOI:
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基金项目:国家自然科学基金项目(31371973,31301700);中央高校基本科研业务费专项(QN2013009)
Synthesis and antifungal activity of 6-bromo-1-isopropenyl-1H-imidazo[4,5b]pyridine-2-one derivatives
HOU Chao,WEI Shaopeng,JI Zhiqin
Abstract:
【Objective】The paper explored the relationship between structure of 6-bromo-1-isopropenyl-1H-imidazo[4,5b]pyridine-2-one amide derivatives and the antifungal activities to provide reference for fungal control.【Method】Starting from 5-bromopyridine-2,3-diamine and ethyl acetoacetate,a series of 6-bromo-1-isopropenyl-1H-imidazo[4,5b]pyridine-2-one derivatives were synthesized.The structures of the synthesized compounds were confirmed by 1H NMR,ESI-MS and elemental analysis.Growth rate method was adopted to test the antifungal activities of these compounds against Fusarium graminearum,Curvularia lunata,Fusarium oxysporumf.sp.vasinfectum,Verticillium dahliae,Fusarium oxysporum and Colletotrichum gloeosporioidesin comparison with azoxystrobin.【Result】Seventeen compounds were synthesized,containing ten aliphatic acid derivatives(B01-B10),six aromatic carboxylic acid derivatives(B11-B16)and one heterocyclic carboxylic acid derivative(B17).When the mass concentration was 100 μg/mL,antifungal activity tests indicated that B01,B03-B06,and B13 exhibited significant inhibitory activities against the mycelial growth of tested fungi.B06 had the best inhibition rate of >70% and its EC50 values were 8.23,49.32,21.45,24.87,36.40 and 28.65 μg/mL,respectively,which were higher than those of azoxystrobin.【Conclusion】The synthesized 6-bromo-1-isopropenyl-1H-imidazo[4,5b]pyridine-2-one amide derivatives had antifungal activities against the mycelial growth of the six fungi,and should be further studied.
Key words:  6-bromo-1-isopropenyl-1H-imidazo[4,5b]pyridine-2-one  amide  antifungal activity