部分苯酚衍生物生物降解性的2D和3D-QSBR研究

应用B3LYP/6-311G**水平计算得到的量子化学参数,在实验数据的基础上,建立了部分苯酚衍生物生物降解性能(二氧化碳生成量(PCD))的定量结构-生物降解性相关模型(2D-QSBR),该模型包括分子平均极化率(α)和熵(SΘ)两个参数,其中α对PCD的影响更为显著,模型的相关系数R2=0.933,交叉验证相关系数q2=0.894.该结果优于midix,6-31G*计算水平下得到的2D模型,此外,应用基于分子模拟技术的比较分子相似性指数(CoMSIA)方法,建立了3D-QSBR模型,模型的R2=0.964,q2=0.716,化合物的氢键供受体特性对降解能力的影响较为显著,其次是化合物的疏水性.结果表明,2D和3D-QSBR模型都具有良好的稳定性和预测能力,可以预测同类化合物的PCD值.

2D and 3D quantitative structure-biodegradability relationship study of phenol derivatives

Based on the experimental data of production of carbon dioxide (PCD) of phenol derivatives, a 2D-QSBR model was established between PCD and quantum chemistry parameters on phenol derivatives which were calculated at B3LYP/6-311G** level. The 2D-QSBR model contains two variables: molecular average polarizability (α) and standard entropy (S^Θ). α has greater effect on PCD than SΘ. The correlation coefficients (R²) and cross-validation correlation coefficients (q²) of the 2D-QSBR model at B3LYP/6-311G** level are 0.933 and 0.894, respectively, showing the priority of this model over models based on midix and 6-31G* level. Correspondingly, a 3D-QSBR model was also established using comparative molecular similarity index analysis (CoMSIA). The R² and q² of CoMSIA model are 0.964 and 0.716, respectively. The 3D contour maps suggested that the H-bonding donor and H-bonding acceptor factors have greater impact on PCD, and hydrophobic factors also have significant effect on PCD. The result indicates that the 2D-QSBR and 3D-QSBR models have strong stability and good predictability.