2-氨基酚衍生物的合成、荧光性质和比较研究:来自DFT、拓扑、非共价相互作用和分子对接研究的见解。

IF 3.1 4区 化学 Q2 BIOCHEMICAL RESEARCH METHODS
Natarajan Elangovan, R Yogeswaran, G Ajithkumar, S K Elagan, Samy F Mahmoud
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引用次数: 0

摘要

本研究采用缩合反应合成了席夫碱,并用1H和13C NMR、FT-IR、UV-Vis和荧光光谱对其进行了全面表征。结构分析表明,这些化合物主要以e构象存在,由分子内六元环氢键稳定。值得注意的是,氯官能化的席夫碱表现出一个额外的弱分子内C-H···Cl氢键。光物理研究表明,化合物2AM24Cl和SA2AM仅表现出长波发射。此外,利用DFT和TD-DFT计算分析了其几何结构、FMOs和吸收光谱。FMO研究计算出2AM24CL和SA2AM的能隙分别为3.54 eV和3.65 eV。化合物2AM24Cl和SA2AM具有较好的发射(荧光)光谱,两者在理论荧光光谱上有较好的匹配。电子密度分布通过彩色映射表示可视化。分子对接研究表明,这些希夫碱衍生物与氨基酸残基之间存在显著的相互作用,增强了它们潜在的生物学相关性。2AM24CL的最低结合能为-5.45 kcal/mol, SA2AM的最低结合能为-5.66 kcal/mol, 2AM24CL和SA2AM的抑制常数分别为101.54 μm和71.33 μm。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Synthesis, Fluorescence Properties and Comparison Studies on 2-aminophenol Derivatives: Insights from DFT, Topology, Non-covalent Interactions and Molecular Docking Studies.

In this study, Schiff base was synthesized under condensation reaction and thoroughly characterized using 1H and 13C NMR, FT-IR, UV-Vis, and fluorescence spectroscopy. Structural analysis revealed that these compounds predominantly exist in the E-conformation, stabilized by an intramolecular six-membered-ring hydrogen bond. Notably, chloro-functionalized Schiff bases exhibit an additional weak intramolecular C-H···Cl hydrogen bond. Photophysical studies indicate that compounds 2AM24Cl and SA2AM exclusively exhibit long-wavelength emission. Furthermore, the geometric structures, FMOs, and absorption spectrum were elucidated using DFT and TD-DFT calculations. The FMO study calculated energy gaps are 3.54 eV and 3.65 eV for 2AM24CL and SA2AM, respectively. The compounds 2AM24Cl and SA2AM show a good emission (fluorescence) spectrum, it good matched in theoretical fluorescence spectrum. Electron density distribution was visualized through color-mapped representations. Molecular docking studies demonstrated significant interactions between these Schiff base derivatives and amino acid residues, reinforcing their potential biological relevance. The 2AM24CL compound's lowest binding energy is -5.45 kcal/mol and the SA2AM compound's lowest binding energy is -5.66 kcal/mol, with an inhibition constant is 101.54 μm for 2AM24Cl and 71.33 μm for SA2AM, respectively.

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来源期刊
Journal of Fluorescence
Journal of Fluorescence 化学-分析化学
CiteScore
4.60
自引率
7.40%
发文量
203
审稿时长
5.4 months
期刊介绍: Journal of Fluorescence is an international forum for the publication of peer-reviewed original articles that advance the practice of this established spectroscopic technique. Topics covered include advances in theory/and or data analysis, studies of the photophysics of aromatic molecules, solvent, and environmental effects, development of stationary or time-resolved measurements, advances in fluorescence microscopy, imaging, photobleaching/recovery measurements, and/or phosphorescence for studies of cell biology, chemical biology and the advanced uses of fluorescence in flow cytometry/analysis, immunology, high throughput screening/drug discovery, DNA sequencing/arrays, genomics and proteomics. Typical applications might include studies of macromolecular dynamics and conformation, intracellular chemistry, and gene expression. The journal also publishes papers that describe the synthesis and characterization of new fluorophores, particularly those displaying unique sensitivities and/or optical properties. In addition to original articles, the Journal also publishes reviews, rapid communications, short communications, letters to the editor, topical news articles, and technical and design notes.
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