title: Nitromethylene neonicotinoids analogues with tetrahydropyrimidine fixed cis-configuration: synthesis, insecticidal activities, and molecular docking studies.
abstract: Two series of new nitromethylene neonicotinoid analogues (2a-2h and 3a-3h) were designed and prepared, with the cis-configuration confirmed by X-ray diffraction. Preliminary bioassays showed that most analogues exhibited excellent insecticidal activities at 500 mg/L, and analogues with optical activity (2c-2g) were highly potent at 100 mg/L, while compound 2d had >90% mortality at 20 mg/L, which suggested that it could be used as a lead for future insecticides development. Modeling the ligand-receptor complexes by molecular docking study explained the structure-activity relationships observed in vitro and revealed an intriguing molecular binding mode at the active site of the nAChR model, thereby possibly providing some useful information for future receptor structure-based designs of novel insecticidal compounds.
authors.affiliation: College of Life and Environment Sciences, Shanghai Normal University, Shanghai, China. willin112@163.com
authors.forename: Chuanwen
authors.initials: C
authors.lastname: Sun
authors.forename: Dingrong
authors.initials: D
authors.lastname: Yang
authors.forename: Jiahua
authors.initials: J
authors.lastname: Xing
authors.forename: Haifeng
authors.initials: H
authors.lastname: Wang
authors.forename: Jia
authors.initials: J
authors.lastname: Jin
authors.forename: Jun
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000818:Animals; D001665:Binding Sites; D019476:Insect Proteins / Q000737:chemistry*; D007313:Insecta / Q000737:chemistry* / Q000187:drug effects; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D011485:Protein Binding; D011978:Receptors, Nicotinic / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D019476:Insect Proteins; D007306:Insecticides; D011978:Receptors, Nicotinic