AlHazmy Sadeq M, Zouaghi Mohamed Oussama, Al-Hakimi Ahmed N, Alorini Thamer, Alhagri Ibrahim A, Arfaoui Youssef, Al-Ashwal Rania, Mansour Lamjed, Hamdi Naceur
Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi Arabia.
Laboratory of Characterizations, Applications & Modeling of Materials (LR18ES08), Department of Chemistry, Faculty of Sciences, University of Tunis El Manar, 2092, Tunis, Tunisia.
Heliyon. 2024 Feb 19;10(5):e26349. doi: 10.1016/j.heliyon.2024.e26349. eCollection 2024 Mar 15.
A new Schiff base, 1-(E)-(4-((E) 4nitrobenzylidene) amino) phenyl)imino) methyl)naphthalen-2-ol (4NMN), was prepared from the reaction of -phenylenediamine with 2-hydroxy-1-naphthaldehyde and 4-nitrobenzaldehyde and characterized with spectroscopic analysis. UV-VIS and NMR. Frontier molecular orbitals, molecular electrostatic potential, and chemical reactivity descriptors of the synthesized compound were studied using molecular modeling methods. The antibacterial and antifungal activities of the Schiff base were studied for its minimum inhibitory concentration. The compound showed a higher effect on yeast than against bacteria. Density functional theory (DFT) calculations were performed to study the mechanism of reaction for the synthesis of 4NMN, and the results were consistent with the experimental findings. 4NMN exhibited moderate antibacterial and antifungal activities and demonstrated higher inhibition potential against different resistant strains compared to the reference drug gentamycin. The absorption and fluorescence spectra of 4NMN were measured in different solvents, and the effect of relative polarity and acidity on the medium was observed. An inner filter effect was observed at high concentrations, and the compound showed considerable fluorescence enhancement with increasing medium viscosity and fluorescence quenching by the addition of traces of Cr and Cu. Additionally, molecular docking studies were conducted to investigate the efficiency of antibacterial and antifungal targets.
一种新的席夫碱，1-(E)-(4-((E)-4-硝基亚苄基)氨基)苯基)亚氨基)甲基)萘-2-醇(4NMN)，由对苯二胺与2-羟基-1-萘甲醛和4-硝基苯甲醛反应制备，并通过光谱分析、紫外可见光谱和核磁共振进行表征。使用分子建模方法研究了合成化合物的前沿分子轨道、分子静电势和化学反应性描述符。研究了席夫碱的抗菌和抗真菌活性的最低抑菌浓度。该化合物对酵母的作用比对细菌的作用更强。进行了密度泛函理论(DFT)计算以研究4NMN合成的反应机理，结果与实验结果一致。4NMN表现出中等的抗菌和抗真菌活性，与参考药物庆大霉素相比，对不同耐药菌株具有更高的抑制潜力。在不同溶剂中测量了4NMN的吸收光谱和荧光光谱，并观察了介质的相对极性和酸度的影响。在高浓度下观察到内滤效应，并且该化合物随着介质粘度的增加显示出相当大的荧光增强，并且通过添加痕量的Cr和Cu导致荧光猝灭。此外，进行了分子对接研究以研究抗菌和抗真菌靶点的效率。
