取代-2-苯基异噻唑啉酮化合物的定量构效关系研究

杨星, 闫莹, 周浩, 吴来明, 蔡兰坤

doi:10.16577/j.issn.1001-1560.2022.0240

材料保护 >

2022 , Vol. 55 >Issue 9: 16 - 21

DOI: https://doi.org/10.16577/j.issn.1001-1560.2022.0240

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取代-2-苯基异噻唑啉酮化合物的定量构效关系研究

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(1. 华东理工大学资源与环境工程学院国家环境保护化工过程环境风险评价与控制重点实验室，上海 200237；2. 中国科学院海洋研究所山东省腐蚀科学重点实验室，山东青岛 266000；3. 上海博物馆馆藏文物保存环境国家文物局重点科研基地，上海 200050)

蔡兰坤(1966-)，博士，教授, 主要研究方向为金属及文物材料的腐蚀与防护，电话：13501782591，E - mail：cailankun@126.com

收稿日期: 2022-03-18

修回日期: 2022-04-18

录用日期: 2022-05-31

网络出版日期: 2023-12-23

基金资助

国家自然科学基金(51671117)；国家重点研发计划(2020YFC1522502) 资助

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Study on Quantitative Structure - Activity Relationship of Substituted - 2 - Phenylisothiazolinones Compounds

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(1. National Key Laboratory of Environmental Risk Assessment and Control for Environmental Protection Chemical Processes, School of Resources and Environmental Engineering, East China University of Science and Technology, Shanghai 200237, China;2. Shandong Key Laboratory of Corrosion Science, Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266000, China;3. Key Scientific Research Base of Museum Environment, State Administration for Cultural Heritage, Shanghai Museum, Shanghai 200050, China)

Received date: 2022-03-18

Revised date: 2022-04-18

Accepted date: 2022-05-31

Online published: 2023-12-23

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摘要

定量构效关系是研究化合物的分子结构和抑菌活性的关系，可为预测新型化合物的分子结构，合成、设计新型异噻唑啉酮类化合物提供理论基础。以10种取代 - 2 - 苯基异噻唑啉酮化合物为研究对象，根据定量构效关系(QSAR)研究方法，建立活性参数数据库，在通过量子化学密度泛函理论B3LYP计算方法中的6 - 311G(d,p)基组对10种取代 - 2 - 苯基异噻唑啉酮化合物进行结构优化，得到相应的分子结构参数，采用多元线性回归分析(MLR)筛选出主要影响目标化合物抑菌活性的结构参数，并建立定量构效关系模型。通过相关回归分析发现，影响取代 - 2 - 苯基异噻唑啉酮化合物抗菌活性的主要结构因素为S-N键的键级(BS-N)、最低空轨道与最高占据轨道的能量差(EL-H)以及辛醇-水分配系数(lgP)，所得该类化合物的QSAR模型2具有良好的预测效果。结果表明，减小分子的BS-N、EL-H，提高lgP均有利于增强取代 - 2 - 苯基异噻唑啉酮化合物的抑菌活性。QSAR模型2具有良好的预测能力，对新型异噻唑啉酮化合物的设计合成有较高的参考价值。

关键词： 定量构效关系; 取代 - 2 - 苯基异噻唑啉酮; 多元线性回归; 抑菌活性

本文引用格式

杨星, 闫莹, 周浩, 吴来明, 蔡兰坤 . 取代-2-苯基异噻唑啉酮化合物的定量构效关系研究[J]. 材料保护, 2022 , 55(9) : 16 -21 . DOI: 10.16577/j.issn.1001-1560.2022.0240

Abstract

Quantitative structure - activity relationship studies the relationship between molecular structure and antibacterial activity, which can provide a theoretical basis for predicting the molecular structure of new compounds, synthesizing and designing new isothiazolinone compounds. Taking 10 substituted - 2 - phenylisothiazolinone compounds as research objects, and based on the quantitative structure - activity relationship (QSAR) research method, the activity parameter database was established. The 6 - 311G(d,p) base set in B3LYP calculation method of quantum chemistry density functional theory was used to optimize the structure of the as - mentioned 10 substituted - 2 - phenylisothiazolinone compounds to obtain the corresponding molecular structure parameters. The multiple linear regression (MLR) analysis was used to screen out the main structural parameters affecting the antibacterial activity of the target compounds, and a quantitative structure - activity relationship model was established. The results of correlation regression analysis showed that the main structural factors affecting the antibacterial activity of substituted - 2 - phenylisothiazolinone compounds were the bond order of the S-N bond (BS-N), the energy difference between the lowest unoccupied molecular orbital and the highest occupied molecular orbital (EL-H ), and the octanol - water partition coefficient (lgP). The QSAR model 2 of the obtained compounds had a good prediction effect. Besides, reducing the BS-N and EL-H of the molecule or increasing the lgP was beneficial to enhance the antibacterial activity of the substituted - 2 - phenylisothiazolinone compounds. The QSAR model 2 had a good predictive ability and presented a high reference value for the design and synthesis of new isothiazolinone compounds.

Key words： QSAR; substituted - 2 - phenylisothiazolinones; multiple linear regression; antibacterial activity

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