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.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2014年第2期409-413,共5页
Chinese Journal of Organic Chemistry
基金
国家重点基础研究发展计划(973计划
No.2010CB126100)
国家高技术研究发展计划(863计划
No.2011AA10A207)
"十一五"国家科技支撑计划(No.2011BAE06B01)
国家自然科学基金(No.21272071)资助项目~~
关键词
新烟碱类似物
合成
生物活性
单晶结构
分子对接
neonicotinoid analogue
synthesis
bioactivity
crystal structure
molecular docking
