A quinoline-benzotriazole derivative: Synthesis, crystal structure and characterization by using spectroscopic, DFT and molecular docking methods
In this research, FT-IR, NMR (1H & 13C), mass spectrometry and single-crystal X-ray diffraction has been used to characterize the synthesized 5-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)quinolin-8-ol (DD2) derivative. B3LYP calculations with the 6-31G* and 6–311++G** basis sets have shown that...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715623001558 |
| _version_ | 1797799051696013312 |
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| author | Banacer Himmi Silvia A. Brandán Yusuf Sert Ameed Ahmed Kawther Necmi Dege Emine Berrin Cinar Ahmed El Louzi Khalid Bougrin Khalid Karrouchi |
| author_facet | Banacer Himmi Silvia A. Brandán Yusuf Sert Ameed Ahmed Kawther Necmi Dege Emine Berrin Cinar Ahmed El Louzi Khalid Bougrin Khalid Karrouchi |
| author_sort | Banacer Himmi |
| collection | DOAJ |
| description | In this research, FT-IR, NMR (1H & 13C), mass spectrometry and single-crystal X-ray diffraction has been used to characterize the synthesized 5-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)quinolin-8-ol (DD2) derivative. B3LYP calculations with the 6-31G* and 6–311++G** basis sets have shown that the most stable C2 structure in gas phase and aqueous solution is in agreement with the experimental determined by X-ray diffraction. Higher dipole moments for C2 in aqueous solution, predicted with both methods, are probably related to its higher stability resulting higher volume contraction (ΔV −1.0 Å3) in solution with the B3LYP/6-31G* method. Similar behaviours in the Mulliken and NPA charges but different from MK charges are observed. Bond orders studies reveal that the O15-H16···N17 bonds are present in both media, as was experimentally observed in the solid state. MEP surfaces have evidenced nucleophilic sites on N of triazol ring while weak electrophilic ones on aromatic H of three rings being the H atom of OH the most labile. Gap values support a lower reactivity of C2 in solution, in agreement with the higher stability evidenced by AIM analyses. The higher electronic density on triazol ring could justify that C2 is unstable in solution, as revealed by NBO analyses. Complete assignments of 93 expected vibration normal modes of C2 and a set of scaled force constants were obtained in both media by using harmonic force fields. Comparisons between experimental and theoretical infrared and 1H- and 13C NMR spectra show reasonable concordances. Intermolecular interactions in the crystal packing of DD2 were studied by using Hirshfeld surface analysis. Furthermore, DD2 was investigated against two targets of SARS-CoV-2 (PDB ID: 6WCF and PDB ID: 6Y84) by using molecular docking studies. Finally, drug likeness and ADME properties of DD2 were researched and compared with hydroxychloroquine, remdesivir, oseltamivir, lopinavir, ritonavir molecules associated as SARS-CoV-2 inhibitors. |
| first_indexed | 2024-03-13T04:14:09Z |
| format | Article |
| id | doaj.art-ff9f37d62ba54b08abec8ad077a6909f |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-03-13T04:14:09Z |
| publishDate | 2023-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-ff9f37d62ba54b08abec8ad077a6909f2023-06-21T06:52:34ZengElsevierResults in Chemistry2211-71562023-01-015100916A quinoline-benzotriazole derivative: Synthesis, crystal structure and characterization by using spectroscopic, DFT and molecular docking methodsBanacer Himmi0Silvia A. Brandán1Yusuf Sert2Ameed Ahmed Kawther3Necmi Dege4Emine Berrin Cinar5Ahmed El Louzi6Khalid Bougrin7Khalid Karrouchi8High Institute of Nursing and Health Techniques of Rabat, Ministry of Health, Rabat, Morocco; Laboratory of Plant Chemistry and Organic and Bioorganic Synthesis, URAC23, Faculty of Science, GEOPAC, Mohammed V University in Rabat, MoroccoCátedra de Química General, Instituto de Química Inorgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, Tucumán 4000, Argentina; Corresponding authors.Sorgun Vocational School, Science and Art Faculty-Department of Physics, Yozgat Bozok University, Yozgat, TurkeyDepartment of Physics, Faculty of Artsand Sciences, Ondokuz Mayıs University, Samsun, TurkeyDepartment of Physics, Faculty of Artsand Sciences, Ondokuz Mayıs University, Samsun, TurkeyDepartment of Physics, Faculty of Artsand Sciences, Ondokuz Mayıs University, Samsun, TurkeyLaboratory of Plant Chemistry and Organic and Bioorganic Synthesis, URAC23, Faculty of Science, GEOPAC, Mohammed V University in Rabat, MoroccoLaboratory of Plant Chemistry and Organic and Bioorganic Synthesis, URAC23, Faculty of Science, GEOPAC, Mohammed V University in Rabat, Morocco; Chemical & Biochemical Sciences Green-Process Engineering (CBS-GPE), Mohammed VI Polytechnic University, Lot 660, Hay Moulay Rachid, Benguerir, MoroccoLaboratory of Analytical Chemistry and Bromatology, Team of Formulation and Quality Control of Health Products, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, Morocco; Corresponding authors.In this research, FT-IR, NMR (1H & 13C), mass spectrometry and single-crystal X-ray diffraction has been used to characterize the synthesized 5-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)quinolin-8-ol (DD2) derivative. B3LYP calculations with the 6-31G* and 6–311++G** basis sets have shown that the most stable C2 structure in gas phase and aqueous solution is in agreement with the experimental determined by X-ray diffraction. Higher dipole moments for C2 in aqueous solution, predicted with both methods, are probably related to its higher stability resulting higher volume contraction (ΔV −1.0 Å3) in solution with the B3LYP/6-31G* method. Similar behaviours in the Mulliken and NPA charges but different from MK charges are observed. Bond orders studies reveal that the O15-H16···N17 bonds are present in both media, as was experimentally observed in the solid state. MEP surfaces have evidenced nucleophilic sites on N of triazol ring while weak electrophilic ones on aromatic H of three rings being the H atom of OH the most labile. Gap values support a lower reactivity of C2 in solution, in agreement with the higher stability evidenced by AIM analyses. The higher electronic density on triazol ring could justify that C2 is unstable in solution, as revealed by NBO analyses. Complete assignments of 93 expected vibration normal modes of C2 and a set of scaled force constants were obtained in both media by using harmonic force fields. Comparisons between experimental and theoretical infrared and 1H- and 13C NMR spectra show reasonable concordances. Intermolecular interactions in the crystal packing of DD2 were studied by using Hirshfeld surface analysis. Furthermore, DD2 was investigated against two targets of SARS-CoV-2 (PDB ID: 6WCF and PDB ID: 6Y84) by using molecular docking studies. Finally, drug likeness and ADME properties of DD2 were researched and compared with hydroxychloroquine, remdesivir, oseltamivir, lopinavir, ritonavir molecules associated as SARS-CoV-2 inhibitors.http://www.sciencedirect.com/science/article/pii/S2211715623001558QuinolineBenzotriazoleCrystal structureDFTMolecular dockingAntiviral |
| spellingShingle | Banacer Himmi Silvia A. Brandán Yusuf Sert Ameed Ahmed Kawther Necmi Dege Emine Berrin Cinar Ahmed El Louzi Khalid Bougrin Khalid Karrouchi A quinoline-benzotriazole derivative: Synthesis, crystal structure and characterization by using spectroscopic, DFT and molecular docking methods Results in Chemistry Quinoline Benzotriazole Crystal structure DFT Molecular docking Antiviral |
| title | A quinoline-benzotriazole derivative: Synthesis, crystal structure and characterization by using spectroscopic, DFT and molecular docking methods |
| title_full | A quinoline-benzotriazole derivative: Synthesis, crystal structure and characterization by using spectroscopic, DFT and molecular docking methods |
| title_fullStr | A quinoline-benzotriazole derivative: Synthesis, crystal structure and characterization by using spectroscopic, DFT and molecular docking methods |
| title_full_unstemmed | A quinoline-benzotriazole derivative: Synthesis, crystal structure and characterization by using spectroscopic, DFT and molecular docking methods |
| title_short | A quinoline-benzotriazole derivative: Synthesis, crystal structure and characterization by using spectroscopic, DFT and molecular docking methods |
| title_sort | quinoline benzotriazole derivative synthesis crystal structure and characterization by using spectroscopic dft and molecular docking methods |
| topic | Quinoline Benzotriazole Crystal structure DFT Molecular docking Antiviral |
| url | http://www.sciencedirect.com/science/article/pii/S2211715623001558 |
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