Radical Scavenging Activity: DFT and Multilinear Regression Studies of Benzofuran-1,3-thiazolidin-4-one Derivatives.

IF 1.2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Fella Ati, Soraya Abtouche, Boubekeur Maouche, Meziane Brahimi
{"title":"Radical Scavenging Activity: DFT and Multilinear Regression Studies of Benzofuran-1,3-thiazolidin-4-one Derivatives.","authors":"Fella Ati, Soraya Abtouche, Boubekeur Maouche, Meziane Brahimi","doi":"10.17344/acsi.2024.8963","DOIUrl":null,"url":null,"abstract":"<p><p>The free radical scavenging activity of benzofuran Schiff base and thiazolidinone derivatives has been investigated using the density functional theory (DFT) calculations. Three primary mechanisms were developed: sequential proton loss electron transfer (SPLET), single electron transfer followed by proton transfer (SET-PT), and hydrogen atom transfer (HAT). Several thermodynamic descriptors were computed in both gas and solvent phases at the B3LYP/6-311G and 6-311G (d, p) level of theory. Our findings suggest that compounds 3a, 3c, 3f, 4d, and 4e may scavenge free radicals through one of these three pathways. The results indicate that SPLET is favored in polar environments, while HAT is the thermodynamically preferred mechanism in the gas phase and non-polar solutions. Electron-withdrawing groups (EWG) attached to the π conjugated system at the N position of the benzofuran derivatives decrease bond dissociation enthalpies (BDE), while electron-donating groups (EDGs) are helpful to decrease the ionization potentials (IPs). The results of the multilinear regression statistical analyses indicate a good correlation between the IC50 and ionization potential, in addition to the proton dissociation enthalpy, proton affinity, and the electron transfer enthalpy descriptors.</p>","PeriodicalId":7122,"journal":{"name":"Acta Chimica Slovenica","volume":"72 2","pages":"359-370"},"PeriodicalIF":1.2000,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta Chimica Slovenica","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.17344/acsi.2024.8963","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

Abstract

The free radical scavenging activity of benzofuran Schiff base and thiazolidinone derivatives has been investigated using the density functional theory (DFT) calculations. Three primary mechanisms were developed: sequential proton loss electron transfer (SPLET), single electron transfer followed by proton transfer (SET-PT), and hydrogen atom transfer (HAT). Several thermodynamic descriptors were computed in both gas and solvent phases at the B3LYP/6-311G and 6-311G (d, p) level of theory. Our findings suggest that compounds 3a, 3c, 3f, 4d, and 4e may scavenge free radicals through one of these three pathways. The results indicate that SPLET is favored in polar environments, while HAT is the thermodynamically preferred mechanism in the gas phase and non-polar solutions. Electron-withdrawing groups (EWG) attached to the π conjugated system at the N position of the benzofuran derivatives decrease bond dissociation enthalpies (BDE), while electron-donating groups (EDGs) are helpful to decrease the ionization potentials (IPs). The results of the multilinear regression statistical analyses indicate a good correlation between the IC50 and ionization potential, in addition to the proton dissociation enthalpy, proton affinity, and the electron transfer enthalpy descriptors.

苯并呋喃-1,3-噻唑烷-4-酮衍生物自由基清除活性的DFT和多元线性回归研究。
采用密度泛函理论(DFT)对苯并呋喃希夫碱和噻唑烷酮衍生物的自由基清除活性进行了研究。主要有三种机制:顺序质子损失电子转移(SPLET)、单电子转移后质子转移(SET-PT)和氢原子转移(HAT)。在B3LYP/6-311G和6-311G (d, p)理论水平上计算了气相和溶剂相的几个热力学描述符。我们的发现表明化合物3a、3c、3f、4d和4e可能通过这三种途径之一清除自由基。结果表明,SPLET在极性环境中更受青睐,而HAT在气相和非极性溶液中更受青睐。苯并呋喃衍生物的N位π共轭体系上的吸电子基团(EWG)降低了键解离焓(BDE),而给电子基团(edg)则有助于降低电离势(IPs)。多元线性回归统计分析结果表明,IC50与电离势、质子解离焓、质子亲和和电子转移焓描述符之间存在良好的相关性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
Acta Chimica Slovenica
Acta Chimica Slovenica 化学-化学综合
CiteScore
2.50
自引率
25.00%
发文量
80
审稿时长
1.0 months
期刊介绍: Is an international, peer-reviewed and Open Access journal. It provides a forum for the publication of original scientific research in all fields of chemistry and closely related areas. Reviews, feature, scientific and technical articles, and short communications are welcome.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信