基于密度泛函理论的氯喹分子反应活性位点预测  

Prediction of Active Reaction Sites of Chloroquine Molecule Based on Density Functional Theory

作　　者：唐海飞 吴梅青 陈丹 颜涛 Tang Haifei(Xiangtan Medicine&Health Vocational College,Xiangtan 411104)

机构地区：[1]湘潭医卫职业技术学院,湖南湘潭411104

出　　处：《黑龙江医药》2022年第3期500-504,共5页Heilongjiang Medicine journal

基　　金：湖南省教育厅科学研究项目(编号:20C1803)。

摘　　要：目的:深入研究氯喹分子反应活性位点,为分子水平理解氯喹的结构特点、药理作用及构效关系提供理论参考;方法:根据量子化学密度泛函理论计算方法,利用Gaussian 09软件对氯喹分子结构进行优化,再利用Multiwfn软件对表面静电势、平均局部离子化能、前线分子轨道、原子电荷及概念密度泛函活性指数进行计算分析;结果:喹啉环N原子、叔胺N原子及亚氨基N原子附近表面静电势较小,平均局部离子化能较低,为HOMO轨道,具有较多负电荷,较高f-值;亚氨基H原子具有较大表面静电势和较大原子电荷值。 结论: 氯喹分子主要存在亲电反应位点,氯喹分子中喹啉环N原子、叔胺N原子及亚氨基N原子为亲电反应活性位点。亲核反应活性位点亚氨基H原子及喹啉环部分C原子。Objective:In order to provide theoretical reference for understanding the structural characteristics,pharmacological effects and structure-activity relationship of chloroquine at the molecular level,the active reaction sites of chloroquine molecule were deeply researched.Methods:According to the calculation method of quantum chemical density functional theory,Gaussian 09 software was used to optimize the molecular structure of chloroquine,and then the surface electrostatic potential,average local ionization energy,frontline molecular orbital,atomic charge and conceptual density functional activity index were calculated and analyzed by Multiwfn software.Results:quinoline ring N atom has a minimum point of electrostatic potential on the surface of the molecule,and the average local ionization energy is low.It is a HOMO orbital with more negative charges and a higher f-value.The imino H atom has a larger surface electrostatic potential and a larger atomic charge value.Conclusions:The chloroquine molecule mainly has electrophilic reaction sites,and the quinoline ring N atom,tertiary amine N atom and imino N atom in the chloroquine molecule are the electrophilic reaction active sites.The nucleophilic reaction active site imino H atom and part of the C atom in the quinoline ring.

关 键 词：氯喹 反应活性位点 表面静电势 平均局部离子化能 原子电荷 

分 类 号：O641[理学—物理化学]