title: Seven-membered azabridged neonicotinoids: synthesis, crystal structure, insecticidal assay, and molecular docking studies.
abstract: 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.
authors.affiliation: Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology , Shanghai 200237, China.
authors.forename: Renbo
authors.initials: R
authors.lastname: Xu
authors.forename: Ming
authors.initials: M
authors.lastname: Luo
authors.forename: Rui
authors.initials: R
authors.lastname: Xia
authors.forename: Xiaoqing
authors.initials: X
authors.lastname: Meng
authors.forename: Xiaoyong
authors.initials: X
authors.lastname: Xu
authors.forename: Zhiping
authors.initials: Z
authors.lastname: Xu
authors.forename: Jiagao
authors.initials: J
authors.lastname: Cheng
authors.forename: Xusheng
authors.initials: X
authors.lastname: Shao
authors.forename: Houju
authors.initials: H
authors.lastname: Li
authors.forename: Zhong
authors.initials: Z
authors.lastname: Li
mesh_terms: D000818:Animals; D001042:Aphids / Q000187:drug effects; D001681:Biological Assay; D018360:Crystallography, X-Ray; D006430:Hemiptera / Q000187:drug effects; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects
chemical_list: D007306:Insecticides
keywords: cycloxaprid; insecticide; neonicotinoids; seven-membered azabridge