马来酸酯类化合物结构与抑菌活性密度泛函理论研究  

Structure-antibacterial activity relationship of maleic ether compound by density functional theory

作　　者：李鸣建[1] 陈艳[1] 冯长君[1] 

机构地区：[1]徐州工程学院化学化工学院,江苏徐州221111

出　　处：《南京理工大学学报》2014年第5期695-700,共6页Journal of Nanjing University of Science and Technology

基　　金：国家自然科学基金(21075138);环境模拟与污染控制国家重点联合实验室开放基金(13K02ESPCT);徐州市科技局计划项目(XM13B111)

摘　　要：采用量子化学密度泛函理论(DFT)研究马来酸酯类化合物对油菜菌核病菌抗菌活性EM50的构效关系(QSAR)。在DFT-B3LYP方法及基组6-31G(d)水平下,对14种马来酸酯类化合物分子进行几何及电子结构全优化,选择最高占据轨道能EHOMO,次最高占据轨道能ENHOMO,最低空轨道能ELUMO,次最低空轨道能ENLUMO,分子中原子的净电荷QZ,偶极矩μ,零点振动能Ev,分子总能量E,热容Cv和熵Sm等作为量子化学描述符qL。通过最佳变量子集回归分析筛选出影响EM50的主要因素,并建立了QSAR模型。通过留一法交叉分析和方差膨胀因子法检测发现,模型具有良好的稳定性及预测能力。拟合的判定系数R2及交叉验证系数R2cv分别为0.910,0.818。分析结果表明,EHOMO和O7原子上净电荷QO7是影响油菜菌核病菌抗菌活性的主要因素。EHOMO越高,抑菌活性越强;QO7越大,抑菌活性越弱。该文QSAR模型可为设计具有高抑菌活性的马来酸酯类化合物提供理论参考。The density functional theory （DFT） method of quantum chemistry is used to study the quarititative structure-activity relationship （QSAR） of the antibacterial activities EM50 of 14 maleic ether compounds to sclerotinia sclerotiorum. The DFT-B3LYP method with the basic set 6-31G（d） is employed to calculate the molecular geometries and electronic structures of 14 maleic ether molecules. The energy of the highest occupied molecular orbital EHOMO, the energy of the lowest unoccupied molecular orbital ELUM0, the energy of the next lowest unoccupied molecular orbital ENnOMO, the energy of the next highest occupied molecular orbital ENLUMO, the net charge of atoms in molecules Qz, the dipole moment μ, the vibrational energy at OK Ev, the total energy E, the heat capacity Cv and the entropy Sm are selected as structural descriptors qL- The main independent factors affecting the antibacterial activities EM50 is determined by leaps-and-bounds regression analysis, and then satisfactory QSAR model is established. The good stability and predictive ability of the model are examined by the leave-one-out（LOO） cross-validation method and variance inflation factors Vtr. The fitting correlation coefficient R2 and the cross-validation coefficient R^2 v are 0. 910 and 0. 818,re- spectively. The result suggests that the energy of highest occupied molecular orbital EHOMO and the net charge Qo7 of 07 atom are the predominant factors affecting the antibacterial activity against sclerotinia sclerotiorum. The antibacterial activity of the compounds increase with the increase of the EnOMO; however,the higher the Q O7 is,the lower the antibacterial activity is. The models may be used as the theoretical reference for the design of new maleic ether compounds with high antibacterial activities.

关 键 词：计算化学 马来酸酯 抑菌活性 油菜菌核病菌 密度泛函理论 构效关系 

分 类 号：S482.2[农业科学—农药学] O6-051[农业科学—植物保护]