College of Life and Environment Sciences, Shanghai Normal University, Shanghai, China.
J Agric Food Chem. 2010 Mar 24;58(6):3415-21. doi: 10.1021/jf904397k.
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.
两个系列的新型硝基亚甲基烟碱类似物（2a-2h 和 3a-3h）被设计和制备，通过 X 射线衍射证实为顺式构型。初步的生物测定表明，大多数类似物在 500mg/L 时表现出优异的杀虫活性，具有光学活性的类似物（2c-2g）在 100mg/L 时具有很高的活性，而化合物 2d 在 20mg/L 时的死亡率超过 90%，这表明它可能被用作未来杀虫剂开发的先导化合物。通过分子对接研究模拟配体-受体复合物，解释了在体外观察到的构效关系，并揭示了在 nAChR 模型的活性部位的一种有趣的分子结合模式，从而可能为未来基于受体结构的新型杀虫化合物的设计提供一些有用的信息。
