An efficient synthesis, structural analysis, and computational studies of benzothiazole derivatives activated by formic acid under solvent-free conditions
In the present work, formic acid was used as a low-cost and eco-friendly catalyst to synthesize 2-(2-hydroxyphenyl)benzothiazole (HB) through a cycloaddition process in a solvent-free reaction medium. Imine molecule was synthesized with the help of acetic acid (B). The ring closure and formation of...
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| Format: | Article |
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Elsevier
2024-06-01
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| Series: | Chemical Physics Impact |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2667022423002414 |
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| author | Karzan Aziz Abdalkarim Sewara Jalal Mohammed Aso Hameed Hasan Khalid M. Omer Francisxavier Paularokiadoss Rebaz Fayaq Hamarouf Kosar Hikmat Hama Aziz Hanar Qadir Hassan Thayalaraj Christopher Jeyakumar |
| author_facet | Karzan Aziz Abdalkarim Sewara Jalal Mohammed Aso Hameed Hasan Khalid M. Omer Francisxavier Paularokiadoss Rebaz Fayaq Hamarouf Kosar Hikmat Hama Aziz Hanar Qadir Hassan Thayalaraj Christopher Jeyakumar |
| author_sort | Karzan Aziz Abdalkarim |
| collection | DOAJ |
| description | In the present work, formic acid was used as a low-cost and eco-friendly catalyst to synthesize 2-(2-hydroxyphenyl)benzothiazole (HB) through a cycloaddition process in a solvent-free reaction medium. Imine molecule was synthesized with the help of acetic acid (B). The ring closure and formation of the thiazole moiety give acetic acid distinctiveness as a catalyst. The cyclization of fused HB failed without an acid catalyst. The chemical structures were characterized using microanalysis techniques such as IR, 1H-NMR, and 13C-NMR. The obtained FT-IR spectra were compared to theoretical data using the B3LYP/6-31G* level of theory. The electronic characteristics of molecules can be predicted utilizing wave function-dependent features, such as Average localized ionization energy (ALIE), Localized orbital locator (LOL), Electron localized function (ELF), Reduced density gradient (RDG), and Noncovalent interactions NCI studies, which have provided a wealth of knowledge. The molecular docking study was investigated to explore binding energy and interaction type. Docking analysis displayed binding energies (kcal/mol) of HB with values of -8.29, -6.80, -6.68, -7.43, and -6.69 of acetylcholinesterase (AChE) and butylcholinesterase (BuChE)), SARS-CoV-2 main protease (Mpro), human immunodeficiency virus reverse transcription (HIV RT)) and cytochrome (P450), respectively, which was the most active compound against all receptors. The dramatic improvement of the proposed approach over the existing methods can be used to derive an efficient and successful route for the synthesis of HB. This process provides a fresh and high-yield method for the synthesis of benzimidazoles. |
| first_indexed | 2024-03-09T02:00:24Z |
| format | Article |
| id | doaj.art-1c0a1b923ac84a6887f0824cfa9e5333 |
| institution | Directory Open Access Journal |
| issn | 2667-0224 |
| language | English |
| last_indexed | 2024-03-09T02:00:24Z |
| publishDate | 2024-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Chemical Physics Impact |
| spelling | doaj.art-1c0a1b923ac84a6887f0824cfa9e53332023-12-08T04:46:55ZengElsevierChemical Physics Impact2667-02242024-06-018100402An efficient synthesis, structural analysis, and computational studies of benzothiazole derivatives activated by formic acid under solvent-free conditionsKarzan Aziz Abdalkarim0Sewara Jalal Mohammed1Aso Hameed Hasan2Khalid M. Omer3Francisxavier Paularokiadoss4Rebaz Fayaq Hamarouf5Kosar Hikmat Hama Aziz6Hanar Qadir Hassan7Thayalaraj Christopher Jeyakumar8Department of Chemistry, College of Science, University of Sulaimani, Qliasan Street, Kurdistan, Slemani 46002, Iraq; Pharmacy Department, College of Medicine, Komar University of Science and Technology, Qularaise, Kurdistan Region, Sulaymania 46002, Iraq; Corresponding author at: Department of Chemistry, College of Science, University of Sulaimani, Qliasan Street, Kurdistan, Slemani 46002, IraqDepartment of Chemistry, College of Science, University of Sulaimani, Qliasan Street, Kurdistan, Slemani 46002, Iraq; Anesthesia Department, College of Health Sciences, Cihan University Sulaimaniya, Sulaimaniya 46001, Kurdistan, IraqDepartment of Chemistry, College of Science, University of Garmian, Bardesur Street, Kurdistan, Kalar 46021, Iraq; Corresponding authors.Department of Chemistry, College of Science, University of Sulaimani, Qliasan Street, Kurdistan, Slemani 46002, IraqPG and Research Department of Chemistry, St. Joseph's College of Arts and Science (Autonomous), Cuddalore, Tamil Nadu 607001, IndiaDepartment of Chemistry, College of Science, University of Sulaimani, Qliasan Street, Kurdistan, Slemani 46002, IraqDepartment of Chemistry, College of Science, University of Sulaimani, Qliasan Street, Kurdistan, Slemani 46002, Iraq; Department of Medical Laboratory of Science, College of Health Sciences, University of Human Development, Sulaimaniyah, IraqDepartment of Chemistry, College of Science, University of Sulaimani, Qliasan Street, Kurdistan, Slemani 46002, IraqPG and Research Department of Chemistry, The American College (Autonomous), Madurai, Tamil Nadu 625002, India; Corresponding authors.In the present work, formic acid was used as a low-cost and eco-friendly catalyst to synthesize 2-(2-hydroxyphenyl)benzothiazole (HB) through a cycloaddition process in a solvent-free reaction medium. Imine molecule was synthesized with the help of acetic acid (B). The ring closure and formation of the thiazole moiety give acetic acid distinctiveness as a catalyst. The cyclization of fused HB failed without an acid catalyst. The chemical structures were characterized using microanalysis techniques such as IR, 1H-NMR, and 13C-NMR. The obtained FT-IR spectra were compared to theoretical data using the B3LYP/6-31G* level of theory. The electronic characteristics of molecules can be predicted utilizing wave function-dependent features, such as Average localized ionization energy (ALIE), Localized orbital locator (LOL), Electron localized function (ELF), Reduced density gradient (RDG), and Noncovalent interactions NCI studies, which have provided a wealth of knowledge. The molecular docking study was investigated to explore binding energy and interaction type. Docking analysis displayed binding energies (kcal/mol) of HB with values of -8.29, -6.80, -6.68, -7.43, and -6.69 of acetylcholinesterase (AChE) and butylcholinesterase (BuChE)), SARS-CoV-2 main protease (Mpro), human immunodeficiency virus reverse transcription (HIV RT)) and cytochrome (P450), respectively, which was the most active compound against all receptors. The dramatic improvement of the proposed approach over the existing methods can be used to derive an efficient and successful route for the synthesis of HB. This process provides a fresh and high-yield method for the synthesis of benzimidazoles.http://www.sciencedirect.com/science/article/pii/S2667022423002414Formic-acidSolvent-less reactionBenzothiazoleWave function-dependentMolecular docking |
| spellingShingle | Karzan Aziz Abdalkarim Sewara Jalal Mohammed Aso Hameed Hasan Khalid M. Omer Francisxavier Paularokiadoss Rebaz Fayaq Hamarouf Kosar Hikmat Hama Aziz Hanar Qadir Hassan Thayalaraj Christopher Jeyakumar An efficient synthesis, structural analysis, and computational studies of benzothiazole derivatives activated by formic acid under solvent-free conditions Chemical Physics Impact Formic-acid Solvent-less reaction Benzothiazole Wave function-dependent Molecular docking |
| title | An efficient synthesis, structural analysis, and computational studies of benzothiazole derivatives activated by formic acid under solvent-free conditions |
| title_full | An efficient synthesis, structural analysis, and computational studies of benzothiazole derivatives activated by formic acid under solvent-free conditions |
| title_fullStr | An efficient synthesis, structural analysis, and computational studies of benzothiazole derivatives activated by formic acid under solvent-free conditions |
| title_full_unstemmed | An efficient synthesis, structural analysis, and computational studies of benzothiazole derivatives activated by formic acid under solvent-free conditions |
| title_short | An efficient synthesis, structural analysis, and computational studies of benzothiazole derivatives activated by formic acid under solvent-free conditions |
| title_sort | efficient synthesis structural analysis and computational studies of benzothiazole derivatives activated by formic acid under solvent free conditions |
| topic | Formic-acid Solvent-less reaction Benzothiazole Wave function-dependent Molecular docking |
| url | http://www.sciencedirect.com/science/article/pii/S2667022423002414 |
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