Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology , Shanghai 200237, China.
J Agric Food Chem. 2014 Nov 19;62(46):11070-9. doi: 10.1021/jf504014y. Epub 2014 Nov 10.
To study the influence of the ring sizes, 37 novel seven-membered azabridged neonicotinoid analogues were synthesized by reactions of nitromethylene analogues, succinaldehyde, and aniline hydrochlorides. Most of the title compounds presented higher insecticidal activities than that of imidacloprid (IMI), cycloxaprid (CYC), and eight-membered compounds against cowpea aphid (Aphis craccivora), armyworm (Pseudaletia separata Walker), and brown planthopper (Nilaparvata lugens), which indicated that introducing the structure of a seven-membered azabridge could significantly improve the insecticidal activities of neonicotinoid analogues. Docking study and binding mode analysis also revealed that introducing methyl group into position 2 of phenyl ring could increase the hydrophobic interactions with receptor, which implied that position 2 might be the key site to get high insecticidal compounds.
为了研究环大小的影响，通过硝基亚甲基类似物、丁二醛和苯胺盐酸盐的反应，合成了 37 种新型的七元氮杂桥接新烟碱类似物。大多数标题化合物对豇豆蚜（Aphis craccivora）、粘虫（Pseudaletia separata Walker）和褐飞虱（Nilaparvata lugens）的杀虫活性均高于吡虫啉（IMI）、环丙烯（CYC）和八元化合物，这表明引入七元氮杂桥结构可显著提高新烟碱类似物的杀虫活性。对接研究和结合模式分析也表明，在苯环的 2 位引入甲基可增加与受体的疏水相互作用，这表明 2 位可能是获得高杀虫化合物的关键位点。
