Synthesis, characterization, and in silico studies of substituted 2,3-dihydro-1,3,4-thiadiazole derivatives
The reaction of hydrazonoyl halides with different carbodithioate derivatives in the presence of triethylamine was studied, resulting in the synthesis of a series of unsymmetrical azine derivatives with yields ranging from 64 % to 80 %. The structures of these compounds were confirmed through spectr...
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Elsevier
2025-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715624006738 |
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| author | Yasser H. Zaki Sobhi M. Gomha Basant Farag Magdi E.A. Zaki Ahmed M. Hussein |
| author_facet | Yasser H. Zaki Sobhi M. Gomha Basant Farag Magdi E.A. Zaki Ahmed M. Hussein |
| author_sort | Yasser H. Zaki |
| collection | DOAJ |
| description | The reaction of hydrazonoyl halides with different carbodithioate derivatives in the presence of triethylamine was studied, resulting in the synthesis of a series of unsymmetrical azine derivatives with yields ranging from 64 % to 80 %. The structures of these compounds were confirmed through spectroscopic analysis (1H NMR, 13C NMR, IR, and mass spectrometry) and elemental analysis. Quantum mechanical calculations were employed to gain deeper insights into the structural and electronic properties of these molecules. Notably, parameters such as heat of formation, net charges, and dipole moments were computed, revealing good agreement between the experimental and theoretical results. This correlation validates the theoretical calculations and further elucidates the stability and reactivity of the unsymmetrical azines. Molecular docking studies further revealed that compounds 5h and 5e achieved the highest docking scores, suggesting potential therapeutic applications. These results, supported by ADMET studies, indicate that substituted 2,3-dihydro-1,3,4-thiadiazole scaffolds hold promise for further development as therapeutic agents. This research advances the understanding of heterocyclic chemistry and underscores the potential for developing new compounds, providing promising opportunities for drug development. |
| format | Article |
| id | doaj-art-071f1d5489e9438aaf2f211e23291876 |
| institution | Kabale University |
| issn | 2211-7156 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj-art-071f1d5489e9438aaf2f211e232918762025-01-29T05:00:46ZengElsevierResults in Chemistry2211-71562025-01-0113101977Synthesis, characterization, and in silico studies of substituted 2,3-dihydro-1,3,4-thiadiazole derivativesYasser H. Zaki0Sobhi M. Gomha1Basant Farag2Magdi E.A. Zaki3Ahmed M. Hussein4Department of Chemistry, Faculty of Science, Beni-Suef University, Beni-Suef 62514, Egypt; Corresponding authors.Department of Chemistry, Faculty of Science, Islamic University of Madinah, Madinah 42351, Saudi Arabia; Corresponding authors.Department of Chemistry, Faculty of Science, Zagazig University, 44519, EgyptDepartment of Chemistry, Faculty of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh 11623, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Beni-Suef University, Beni-Suef 62514, Egypt; Chemistry Department, College of Science and Humanities - Al Quwaiiyah, Shaqra University, Saudi ArabiaThe reaction of hydrazonoyl halides with different carbodithioate derivatives in the presence of triethylamine was studied, resulting in the synthesis of a series of unsymmetrical azine derivatives with yields ranging from 64 % to 80 %. The structures of these compounds were confirmed through spectroscopic analysis (1H NMR, 13C NMR, IR, and mass spectrometry) and elemental analysis. Quantum mechanical calculations were employed to gain deeper insights into the structural and electronic properties of these molecules. Notably, parameters such as heat of formation, net charges, and dipole moments were computed, revealing good agreement between the experimental and theoretical results. This correlation validates the theoretical calculations and further elucidates the stability and reactivity of the unsymmetrical azines. Molecular docking studies further revealed that compounds 5h and 5e achieved the highest docking scores, suggesting potential therapeutic applications. These results, supported by ADMET studies, indicate that substituted 2,3-dihydro-1,3,4-thiadiazole scaffolds hold promise for further development as therapeutic agents. This research advances the understanding of heterocyclic chemistry and underscores the potential for developing new compounds, providing promising opportunities for drug development.http://www.sciencedirect.com/science/article/pii/S2211715624006738Hydrazonoyl halidesCarbodithioatesUnsymmetrical azines1,3-Dipolar cycloadditionQuantum mechanical calculationsIn silico profiling |
| spellingShingle | Yasser H. Zaki Sobhi M. Gomha Basant Farag Magdi E.A. Zaki Ahmed M. Hussein Synthesis, characterization, and in silico studies of substituted 2,3-dihydro-1,3,4-thiadiazole derivatives Results in Chemistry Hydrazonoyl halides Carbodithioates Unsymmetrical azines 1,3-Dipolar cycloaddition Quantum mechanical calculations In silico profiling |
| title | Synthesis, characterization, and in silico studies of substituted 2,3-dihydro-1,3,4-thiadiazole derivatives |
| title_full | Synthesis, characterization, and in silico studies of substituted 2,3-dihydro-1,3,4-thiadiazole derivatives |
| title_fullStr | Synthesis, characterization, and in silico studies of substituted 2,3-dihydro-1,3,4-thiadiazole derivatives |
| title_full_unstemmed | Synthesis, characterization, and in silico studies of substituted 2,3-dihydro-1,3,4-thiadiazole derivatives |
| title_short | Synthesis, characterization, and in silico studies of substituted 2,3-dihydro-1,3,4-thiadiazole derivatives |
| title_sort | synthesis characterization and in silico studies of substituted 2 3 dihydro 1 3 4 thiadiazole derivatives |
| topic | Hydrazonoyl halides Carbodithioates Unsymmetrical azines 1,3-Dipolar cycloaddition Quantum mechanical calculations In silico profiling |
| url | http://www.sciencedirect.com/science/article/pii/S2211715624006738 |
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