Nitromethylene neonicotinoids analogues with tetrahydropyrimidine fixed cis-configuration: synthesis, insecticidal activities, and molecular docking studies.
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.
Sun
Chuanwen
C
College of Life and Environment Sciences, Shanghai Normal University, Shanghai, China. willin112@163.com
Yang
Dingrong
D
Xing
Jiahua
J
Wang
Haifeng
H
Jin
Jia
J
Zhu
Jun
J
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
D019476:Insect Proteins; D007306:Insecticides; D011978:Receptors, Nicotinic