Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology , Shanghai 200237, China.
J Agric Food Chem. 2011 Oct 12;59(19):10615-23. doi: 10.1021/jf2029708. Epub 2011 Sep 16.
On the basis of research of the proposed modes of action between neonicotinoids and insect nicotinic acetylcholine receptor (nAChR), a series of phenylazoneonicotinoids were designed and synthesized to further promote the π-π interaction between molecule and amino acid residues. The target compounds have been identified on the basis of satisfactory analytical and spectral ((1)H NMR, (13)C NMR, HRMS, and X-ray) data. The preliminary results revealed that tiny differences in substitutes resulted in different configurations and great bioactivity variations. Some compounds with electron-donating groups on positions 2 and 6 of the phenyl ring presented higher insecticidal activity than imidacloprid against cowpea aphids ( Aphis craccivora ). The impressive crystal structure of the excellent insecticidal activity compound 9q clearly proved that the functional electronegative pharmacophore was approximately vertical to the methyleneimidazolidine plane. The differences in the mode of interaction on nAChR of typical compounds 9h and 9q remain unclear.
基于对新烟碱类杀虫剂与昆虫烟碱型乙酰胆碱受体（nAChR）作用模式的研究，设计并合成了一系列苯甲酮基硝基亚砜类化合物，以进一步促进分子与氨基酸残基之间的π-π相互作用。根据令人满意的分析和光谱（1H NMR、13C NMR、高分辨质谱和 X 射线）数据，确定了目标化合物。初步结果表明，取代基的微小差异导致不同的构象和巨大的生物活性变化。一些苯环 2 位和 6 位有供电子基团的化合物对豇豆蚜（Aphis craccivora）的杀虫活性高于吡虫啉。具有优异杀虫活性的化合物 9q 的令人印象深刻的晶体结构清楚地证明了功能电负性药效团大致垂直于亚甲基咪唑烷平面。典型化合物 9h 和 9q 在 nAChR 上的相互作用模式的差异尚不清楚。
