Synthesis, characterization, optical properties, biological activity and theoretical studies of a 4 nitrobenzylidene) amino) phenyl)imino)methyl)naphthalen-2-ol -based fluorescent Schiff base
A new Schiff base, 1-(E)-(4-((E) 4nitrobenzylidene) amino) phenyl)imino) methyl)naphthalen-2-ol (4NMN), was prepared from the reaction of p-phenylenediamine with 2-hydroxy-1-naphthaldehyde and 4-nitrobenzaldehyde and characterized with spectroscopic analysis. UV-VIS and NMR. Frontier molecular orbit...
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| Language: | English |
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Elsevier
2024-03-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844024023806 |
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| author | Sadeq M. AlHazmy Mohamed Oussama Zouaghi Ahmed N. Al-Hakimi Thamer Alorini Ibrahim A. Alhagri Youssef Arfaoui Rania Al-Ashwal Lamjed Mansour Naceur Hamdi |
| author_facet | Sadeq M. AlHazmy Mohamed Oussama Zouaghi Ahmed N. Al-Hakimi Thamer Alorini Ibrahim A. Alhagri Youssef Arfaoui Rania Al-Ashwal Lamjed Mansour Naceur Hamdi |
| author_sort | Sadeq M. AlHazmy |
| collection | DOAJ |
| description | A new Schiff base, 1-(E)-(4-((E) 4nitrobenzylidene) amino) phenyl)imino) methyl)naphthalen-2-ol (4NMN), was prepared from the reaction of p-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 Cr1+ and Cu2+. Additionally, molecular docking studies were conducted to investigate the efficiency of antibacterial and antifungal targets. |
| first_indexed | 2024-04-24T23:16:01Z |
| format | Article |
| id | doaj.art-4c607e31b9b546018a580bb11f47fdd4 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-04-24T23:16:01Z |
| publishDate | 2024-03-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-4c607e31b9b546018a580bb11f47fdd42024-03-17T07:55:19ZengElsevierHeliyon2405-84402024-03-01105e26349Synthesis, characterization, optical properties, biological activity and theoretical studies of a 4 nitrobenzylidene) amino) phenyl)imino)methyl)naphthalen-2-ol -based fluorescent Schiff baseSadeq M. AlHazmy0Mohamed Oussama Zouaghi1Ahmed N. Al-Hakimi2Thamer Alorini3Ibrahim A. Alhagri4Youssef Arfaoui5Rania Al-Ashwal6Lamjed Mansour7Naceur Hamdi8Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi ArabiaLaboratory of Characterizations, Applications & Modeling of Materials (LR18ES08), Department of Chemistry, Faculty of Sciences, University of Tunis El Manar, 2092, Tunis, TunisiaDepartment of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi ArabiaDepartment of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi ArabiaDepartment of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi ArabiaLaboratory of Characterizations, Applications & Modeling of Materials (LR18ES08), Department of Chemistry, Faculty of Sciences, University of Tunis El Manar, 2092, Tunis, TunisiaSchool of Biomedical Engineering and Health Sciences, Faculty of Engineering, Universiti Teknologi Malaysia, Johor Bahru, 81310, Malaysia; Advanced Diagnostic and Progressive Human Care Research Group, School of Biomedical Engineering and Health Science Teknologi Malaysia, Johor Bahru, 81310, MalaysiaZoology Department, College of Science, King Saud University, Saudi Arabia, P.O. Box 2455, Riyadh, 11451, Saudi ArabiaResearch Laboratory of Environmental Sciences and Technologies (LR16ES09), Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif, Tunisia; Corresponding author.A new Schiff base, 1-(E)-(4-((E) 4nitrobenzylidene) amino) phenyl)imino) methyl)naphthalen-2-ol (4NMN), was prepared from the reaction of p-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 Cr1+ and Cu2+. Additionally, molecular docking studies were conducted to investigate the efficiency of antibacterial and antifungal targets.http://www.sciencedirect.com/science/article/pii/S2405844024023806FluorescenceDFT calculationsBiological evaluationMolecular dockingQuenchingChemisensors |
| spellingShingle | Sadeq M. AlHazmy Mohamed Oussama Zouaghi Ahmed N. Al-Hakimi Thamer Alorini Ibrahim A. Alhagri Youssef Arfaoui Rania Al-Ashwal Lamjed Mansour Naceur Hamdi Synthesis, characterization, optical properties, biological activity and theoretical studies of a 4 nitrobenzylidene) amino) phenyl)imino)methyl)naphthalen-2-ol -based fluorescent Schiff base Heliyon Fluorescence DFT calculations Biological evaluation Molecular docking Quenching Chemisensors |
| title | Synthesis, characterization, optical properties, biological activity and theoretical studies of a 4 nitrobenzylidene) amino) phenyl)imino)methyl)naphthalen-2-ol -based fluorescent Schiff base |
| title_full | Synthesis, characterization, optical properties, biological activity and theoretical studies of a 4 nitrobenzylidene) amino) phenyl)imino)methyl)naphthalen-2-ol -based fluorescent Schiff base |
| title_fullStr | Synthesis, characterization, optical properties, biological activity and theoretical studies of a 4 nitrobenzylidene) amino) phenyl)imino)methyl)naphthalen-2-ol -based fluorescent Schiff base |
| title_full_unstemmed | Synthesis, characterization, optical properties, biological activity and theoretical studies of a 4 nitrobenzylidene) amino) phenyl)imino)methyl)naphthalen-2-ol -based fluorescent Schiff base |
| title_short | Synthesis, characterization, optical properties, biological activity and theoretical studies of a 4 nitrobenzylidene) amino) phenyl)imino)methyl)naphthalen-2-ol -based fluorescent Schiff base |
| title_sort | synthesis characterization optical properties biological activity and theoretical studies of a 4 nitrobenzylidene amino phenyl imino methyl naphthalen 2 ol based fluorescent schiff base |
| topic | Fluorescence DFT calculations Biological evaluation Molecular docking Quenching Chemisensors |
| url | http://www.sciencedirect.com/science/article/pii/S2405844024023806 |
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