关键词: 反丁烯二酸酯类化合物, 构效关系, 抗菌活性, 计算机模拟, 构型优化, 外部预测

Abstract: The quantitative structure-activity relationship (QSAR) between molecular structures and antibacterial activity of fumaric acid esters was studied using the density functional theory (DFT) at the B3LYP functional at the level of 6-311++G(d) basis set. The energy of the highest occupied molecular orbital E_HOMO,the energy of the lowest unoccupied molecular orbital E_LUMO,the difference of energy DE,the dipole moment μ,the zero-point energy (ZPE) and the average molecular polarizability (p) were selected as the structural descriptors. The geometries and the QSAR model of the samples were optimized and the stable complexes were obtained. The stability and predictive ability of the model were examined by the “leave-one-out” cross-validation method.The results suggest that the dipole moment μ,DE and zero-point energy are the predominant factors affecting the antibacterial activity against B. subtilis. The antifungal activity increases with the increase of DE and μ. The obtained QSAR model has a good stability and predictive ability for such inhibitors.

Key words: fumaric acid esters, structure-activity relationship, antibacterial activity, computer simulation, structure optimization, outer prediction