Seven-membered azabridged neonicotinoids: synthesis, crystal structure, insecticidal assay, and molecular docking studies.
Seven-membered azabridged neonicotinoids: synthesis, crystal structure, insecticidal assay, and molecular docking studies.
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DOI：
10.1021/jf504014y
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发表时间：
2014-11
影响因子：
6.1
通讯作者：
Ren-Rui Xu;Mingjian Luo;Rui Xia;Xiaoqing Meng;Xiaoyong Xu;Zhiping Xu;Jiagao Cheng;X. Shao
中科院分区：
文献类型：
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作者：
Ren-Rui Xu;Mingjian Luo;Rui Xia;Xiaoqing Meng;Xiaoyong Xu;Zhiping Xu;Jiagao Cheng;X. Shao
为了研究环尺寸的影响，以亚甲基类似物、丁二醛和盐酸苯胺为原料合成了37个新型七元偶氮桥新烟碱类似物。标题化合物对豇豆蚜（Aphis cracivora）、粘虫（Pseudaletia separata Walker）和褐飞虱（Nilaparvata lugens）的杀虫活性大多高于吡虫啉（IMI）、环磷酰胺（CYC）和八元化合物，说明引入七元杜鹃花桥结构可显著提高新烟碱类类似物的杀虫活性。对接研究和结合模式分析也表明，在苯基环的2号位置引入甲基可以增加与受体的疏水相互作用，这意味着2号位置可能是获得高杀虫性化合物的关键位点。
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.