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2-(4-取代-苯基)-3-异噻唑啉酮抗菌活性的定量构效关系研究 被引量:10

QSAR Studies on the Antibacterial Activity of Some Substituted 3-Isothiazolinones
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摘要 用密度泛函理论和逐步回归分析方法对22种新合成的2-(4-取代-苯基)-3-异噻唑啉酮化合物进行了结构与抗菌活性研究.通过对平衡几何构型、前线轨道组成和Mulliken电荷分布的分析得出:S(1),N(2)原子是该类化合物的主要活性部位,且5位氯取代的化合物抗菌活性较好.通过回归分析,筛选了影响抗菌活性的主要因素,建立了定量构效关系方程.结果表明,硫原子的亲核前线电子密度、3D-Balaban指数、S(1)—N(2)Wiberg键级和Schultz分子价拓扑指数是影响异噻唑啉酮类化合物抗大肠杆菌活性的主要因素,所得模型对化合物抗菌活性有较好的预报能力. Relationship between structures and antibacterial activities of 22 2-(4-substituted-phenyl)-3- isothiazolinones was studied using both density functional theory (DFT) and stepwise multiple linear regression analysis (SMLR) methods. The equilibrium geometries, the frontier molecular orbital compositions and the distribution of Mulliken charges of these compounds have been investigated and analyzed using the DFT method at the B3LYP/6-311G(d,p) basis set. It was concluded that the S(1) and N(2) atoms were the active sites. Compared with the corresponding unsubstituted analogues, the 5-chloro derivatives were more active against Escherichia coli. The obtained QSAR model indicates that the nucleophilic frontier electron density of S(1) atom (f^N (1) ), 3D-Balaban index (J3D), the Wiberg bond order of S(1)-N(2) (BOSD-N(2)) and Schultz molecular topological index by valence vertex degrees (SMTIV) are the predominant factors affecting antibacterial activity against Escherichia coli ATCC 8739 (Gram-negative bacteria), which could provide theoretical reference to design isothiazolinones with stronger antibacterial activity.
出处 《化学学报》 SCIE CAS CSCD 北大核心 2007年第23期2707-2714,共8页 Acta Chimica Sinica
基金 国家自然科学基金(No.20677053)资助项目.
关键词 异噻唑啉酮 抗菌活性 大肠肝菌 密度泛函 定量构效关系 3-lsothiazolinone antibacterial activity Escherichia coli density functional theory QSAR
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