1-酰基苯并咪唑酮酰胺衍生物的合成及其抗菌活性  

Synthesis and antimicrobial activity of 1-acyl benzimidazolone amide derivatives

作　　者：李方方[1] 魏少鹏[1] 宗兆锋[1] 姬志勤[1] 

机构地区：[1]西北农林科技大学植物保护学院,陕西杨凌712100

出　　处：《农药学学报》2012年第6期597-601,共5页Chinese Journal of Pesticide Science

基　　金：国家重点基础研究发展计划("973"计划)项目(2010CB126105);国家自然科学基金资助项目(30971935)

摘　　要：以邻苯二胺和乙酰乙酸乙酯为起始原料制得异丙烯基苯并咪唑酮(Ⅲ),再经N-酰化反应得到13个苯并咪唑酮酰胺衍生物(Ⅳ-01～Ⅳ-13)以及由Ⅳ-02脱异丙烯基的产物Ⅳ-02a,其中9个为未见文献报道的新化合物。通过核磁共振氢谱和碳谱、质谱以及元素分析对其结构进行了表征。抑菌活性测定结果表明,化合物Ⅳ-01～Ⅳ-03、Ⅳ-11及Ⅳ-02a对供试病原细菌和真菌均表现出明显的抑菌活性,其中化合物Ⅳ-02和Ⅳ-02a尤为突出,且二者活性相近,其中Ⅳ-02对蜡状芽孢杆菌Bacillus cereus(1.184 6)、枯草芽孢杆菌Bacillus subtilis(1.88)、金黄色葡萄球菌Staphylococcus aureus(1.89)和大肠杆菌Escherichia coil(1.157 4)的MIC(抑制生长的最低浓度)值分别为0.78、12.5、1.56和1.56μg/mL,对番茄灰霉病菌Botrytis cinerea的有效抑制中浓度(EC50)为7.02μg/mL。Thirteen benzimidazolone derivatives were synthesized from isopropenyl-benzimidazolone via N-acylation reaction,and o-phenylenediamine and acetoacetic ester were used as starting material.The structures of the new derivatives were confirmed by 1H NMR,13C NMR and ESI-MS spectral analysis.Antimicrobial activity test indicated that compounds Ⅳ-01~Ⅳ-03 and Ⅳ-11,as well as the de-isopropenyl product of Ⅳ-02,Ⅳ-02a,have good inhibitory activity against the tested microbial.The MIC values of compound Ⅳ-02 were 0.78,12.5,1.56 and 1.56 μg/mL against Bacillus cereus,Bacillus subtilis,Staphylococcus aureus and Escherichia coil,and the EC50 value was 7.02 μg/mL against Botrytis cinerea,respectively.The de-isopropenyl product,Ⅳ-02a,showed the similarly antimicrobial activity as that of Ⅳ-02.

关 键 词：苯并咪唑酮 酰胺 合成 抑菌活性 

分 类 号：O626.23[理学—有机化学]