Nitromethylene Neonicotinoids Analogues with Tetrahydropyrimidine Fixed cis-Configuration: Synthesis, Insecticidal Activities, and Molecular Docking Studies

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• 作者：Chuanwen Sun ; Dingrong Yang ; Jiahua Xing ; Haifeng Wang ; Jia Jin ; Jun Zhu
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2010
• 出版时间：March 24, 2010
• 年：2010
• 卷：58
• 期：6
• 页码：3415-3421
• 全文大小：842K
• 年卷期：v.58,no.6(March 24, 2010)
• ISSN：1520-5118

文摘

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.