Discovery of bis-aromatic ring neonicotinoid analogues fixed as cis-configuration: Synthesis, insecticidal activities, and molecular docking studies.
A novel series of bis-aromatic ring neonicotinoid analogues (1a-1l, 2a-2c), were designed and prepared by introducing a new substituted aromatic ring into nitenpyram and forming a tetrahydropyrimidine ring, with the cis-configuration confirmed by X-ray diffraction. Preliminary bioassays showed most analogues exhibited good insecticidal activities at 100mg/L, and compound 1d and 2a were highly potent even at 10mg/L. Modeling the ligand-receptor complexes by molecular docking study explained the structure-activity relationships observed in vitro, which may provide some useful information for future design of new insecticides.
Sun
Chuanwen
C
College of Life and Environment Sciences, Shanghai Normal University, Shanghai 200234, China. willin@shnu.edu.cn
Jin
Jia
J
Zhu
Jun
J
Wang
Haifeng
H
Yang
Dingrong
D
Xing
Jiahua
J
D000691:Anabasine / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008958:Models, Molecular; D008968:Molecular Conformation; D013329:Structure-Activity Relationship; D014961:X-Ray Diffraction
D007306:Insecticides; D000691:Anabasine