紫草素衍生物定量构效关系的量子化学研究

为探讨紫草素衍生物结构与其抗植物病毒活性之间的关系,采用Gaussian 03程序量子化学的从头算法对9种紫草素衍生物进行了量子化学计算。将得到的分子空间结构、轨道能量、轨道组成、净电荷等性质进行分析,并与实验得到的生物活性参数进行对比研究。结果表明:紫草素衍生物的抗植物病毒活性与化合物的前沿分子轨道LUMO能级存在负相关性(R2=0.626 6);此类化合物与受体作用时,可能与受体发生电子转移,形成电子配合物,从而发挥药效;萘醌环结构应为此类化合物的活性关键部位,R基团为有效的结构修饰点。

Quantum study on structure-activity relationship of shikonin derivates

The quantum chemistry calculation of shikonin derivates was carried out by the Gaussian 03 Program Package to investigate the relationship between the structure of shikonin derivates and its activity of anti-phytovirus.The geometrical configuration,orbital energy,orbital composition and net charge of each atom of the molecules were analyzed and the relationship between anti-phytovirus activities and the quantum chemical properties was studied.The conclusions were as follows: 1) the anti-phytovirus activities of shikonin derivates have a linear relationship with energy and composition of LUMO and the LUMO molecular orbitals play important role in the anti-phytovirus activities;2) the active sites of shikonin derivates were at the structure of naphthaquinone,and R groups was an effective structure modified site;3)when the compound molecule interacted with the target acceptor,the electron transfer between the shikonin derivates molecule and the target acceptor might be happened to form the electron-transferred-complex.