新型双环新烟碱类似物的合成及其生物活性有机化学.pdfVIP

DOI: 10.6023/cjoc201308033 研究简报 有机化学 Chinese Journal of Organic Chemistry NOTE 新型双环新烟碱类似物的合成及其生物活性 陈寅波 范 杰 夏 爽 程家高 徐晓勇 李 忠* (上海市化学生物学重点实验室 华东理工大学药学院 上海 200237) 摘要 设计合成了六个新型双环新烟碱类似物, 通过 1H NMR, 13C NMR, 高分辨质谱和单晶结构对目标化合物的结构 进行了表征. 初步的生物活性测试表明: 在 500 mg•L－1 浓度下, 目标化合物6a, 6c～6f 对豆蚜(Aphis craccivora)具有很 好的杀虫活性. 通过分子对接比较并解释了目标化合物 6a 和吡虫啉的活性和作用模式的差异, 其结果表明目标化合物 6a 的吡啶环和受体残基色氨酸 147 的芳香环侧链具有π-π堆积作用, 与吡虫啉的作用方式存在一定差异. 关键词 新烟碱类似物; 合成; 生物活性; 单晶结构; 分子对接 Synthesis and Insecticidal Evaluation of Neonicotinoid Ana- logues with Bicyclic Ring System Chen, Yinbo Fan, Jie Xia, Shuang Cheng, Jiagao Xu, Xiaoyong Li, Zhong* (Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237) Abstract Six novel neonicotinoid analogues with bicyclic ring system were designed and synthesized, and their structures were characterized by 1H NMR, 13C NMR, HRMS and single crystal X-ray diffraction analysis. Preliminary bioassays showed that five target compounds 6a, 6c～6f exhibited good insecticidal activities against cowpea aphids (Aphis craccivora) at 500 mg•L－1. Docking study was applied to investigate the effect of the bicyclic ring system of the target compound 6a on the bio- logical activity, and compared with mode of action of imidacloprid (IMI) and compound 6a. It was found that the only π-π stacking interaction was found between the plane of