苯并吡唑类衍生物的设计、合成、杀虫活性及结合模式研究  

Design,synthesis,insecticidal assay and binding mode study of benzopyrazole derivatives

作　　者：施蔓 周聪 栗广龙 徐晓勇[1] 邵旭升[1] 李忠[1] 程家高[1] SHI Man;ZHOU Cong;LI Guanglong;XU Xiaoyong;SHAO Xusheng;LI Zhong;CHENG Jiagao(Shanghai Key Laboratory of Chemical Biology,School of Pharmacy,East China University of Science and Technology,Shanghai 200237,China)

机构地区：[1]华东理工大学药学院,上海市化学生物学(芳香杂环)重点实验室,上海200237

出　　处：《农药学学报》2023年第5期1047-1056,共10页Chinese Journal of Pesticide Science

基　　金：国家自然科学基金(21977030).

摘　　要：基于新报道的高活性介离子类nAChR调节剂结构,通过骨架跃迁策略设计、合成了30个未见文献报道的苯并吡唑类化合物,所有化合物的结构均通过核磁共振氢谱(^(1)H NMR)、碳谱(^(13)C NMR)及高分辨质谱(HRMS)确证。杀虫活性测试结果表明,目标化合物A1、A7、A16和A22在500 mg/L下对苜蓿蚜的致死率约为40%,活性弱于先导结构化合物1。初步分析,介离子结构与非介离子结构结合模式相近,其理化性质以及静电势表面的差异可能是导致目标化合物活性比化合物1低的主要原因。Based on the recently reported structure of highly active mesoionic nAChR modulators,30 novel benzopyrazole compounds were designed and synthesized through scaffold hopping.Their structures were confirmed by ^(1)H NMR,^(13)C NMR and HRMS.Insecticidal activity assays revealed compounds A1,A7,A16 and A22 showed about 40%mortality against Aphis craccivora at the concentration of 500 mg/L,however still less active than lead compound 1.Preliminary analysis suggests similar binding modes for mesoionic and non-mesoionic structures,and the differences in their physicochemical properties and electrostatic potential surface between A1 and compound 1 may be the main reason for the lower activities of the target compounds than that of compound 1.

关 键 词：苯并吡唑 新烟碱 杀虫活性 烟碱乙酰胆碱受体 结合模式 

分 类 号：O622.26[理学—有机化学] TQ453[理学—化学]