文献类型：期刊文献

中文题名：新型双环新烟碱类似物的合成及其生物活性

英文题名：Synthesis and Insecticidal Evaluation of Neonicotinoid Analogues with Bicyclic Ring System

作者：陈寅波[1];范杰[1];夏爽[1];程家高[1];徐晓勇[1];李忠[1]

机构：[1]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

年份：2014

卷号：34

期号：2

起止页码：409

中文期刊名：有机化学

外文期刊名：Chinese Journal of Organic Chemistry

收录：CSTPCD;;Scopus;WOS:【SCI-EXPANDED(收录号:WOS:000333499500020)】；北大核心:【北大核心2011】；CSCD:【CSCD2013_2014】；

基金：Project supported by the National Basic Research Program of China (973 Program, No. 2010CB126100), the National High Technology Research and Development Program of China (863 Program, No. 2011AA10A207), the National Key Technology R&D Program of China (No. 2011BAE06B01) and the National Natural Science Foundation of China (No. 21272071).

语种：中文

中文关键词：新烟碱类似物;合成;生物活性;单晶结构;分子对接

外文关键词：neonicotinoid analogue; synthesis; bioactivity; crystal structure; molecular docking

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?-?堆积作用,与吡虫啉的作用方式存在一定差异.
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 biological 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 pyridine of the target compounds 6a and the aromatic side chain of Tyr 147, which was different binding mode with that of IMI.