顺式新烟碱类衍生物的三维定量构效关系研究

采用比较分子力场分析法(CoMFA)和比较分子相似性指数分析法(CoMSIA)对34个顺式新烟碱类衍生物的杀虫活性进行三维定量构效关系(3D-QSAR)研究.构建的CoMFA和CoMSIA模型的交叉验证系数rc2v分别为0.877和0.862,非交叉验证系数r2分别为0.970和0.961,表明建立的3D-QSAR模型具有较好的统计相关性和预测能力.一系列的研究结果指出:立体场、静电场和氢键受体场是描述顺式新烟碱类衍生物的化学结构与杀虫活性关系的重要参数;在咪唑啉环的3,4位不宜引入较大的取代基,提高咪唑啉环的电负性或增强硝基一个端氧的氢键受体特征有利于提高顺式新烟碱类衍生物的杀虫活性.

3D Quantitative Structure-Property Relationship Study on cis-Neonicotinoid Derivatives

Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were firstly employed to develop 3D-QSAR model on insecticidal activity of 34 cis-neonicotinoid derivatives. The predictive capability was validated to be good by correlation coefficient of cross-validation with 0.877 and 0.862, and non cross-validation value r² with 0.970 and 0.961 for CoMFA and CoMSIA models, respectively. The obtained results propose that the steric effect, electrostatic effect and hydrogen receptor effect are essential parameters characterized the structure-activity relationship of cis-neonicotinoid derivatives. Large substituent groups at 3- and 4-position of imidazolidine are unfavorable, and the enhancement of electronegativity for imidazolidine or the increasement of hydrogen acceptor character for one oxygen atom of nitro-group is favorable to the insecticidal activity of cis-neonicotinoid derivatives.