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

YANG Xing, YAN Ying, ZHOU Hao, WU Laiming, CAI Lankun

doi:10.16577/j.issn.1001-1560.2022.0240

Materials Protection >

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

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

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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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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YANG Xing, YAN Ying, ZHOU Hao, WU Laiming, CAI Lankun . Study on Quantitative Structure - Activity Relationship of Substituted - 2 - Phenylisothiazolinones Compounds[J]. Materials Protection, 2022 , 55(9) : 16 -21 . DOI: 10.16577/j.issn.1001-1560.2022.0240

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