Green Route Synthesis and Molecular Docking of Azines Using Cellulose Sulfuric Acid under Microwave Irradiation
A novel catalytic approach for the synthesis of symmetric and asymmetric azines has been developed. The environmentally benign protocol was achieved via condensation of 1-[(2-thienyl)ethylidene]hydrazine (<b>1</b>) with different aromatic aldehydes <b>2a</b>–<b>h</b&...
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MDPI AG
2023-02-01
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| author | Sobhi M. Gomha Sayed M. Riyadh Reem A. K. Alharbi Magdi E. A. Zaki Tariq Z. Abolibda Basant Farag |
| author_facet | Sobhi M. Gomha Sayed M. Riyadh Reem A. K. Alharbi Magdi E. A. Zaki Tariq Z. Abolibda Basant Farag |
| author_sort | Sobhi M. Gomha |
| collection | DOAJ |
| description | A novel catalytic approach for the synthesis of symmetric and asymmetric azines has been developed. The environmentally benign protocol was achieved via condensation of 1-[(2-thienyl)ethylidene]hydrazine (<b>1</b>) with different aromatic aldehydes <b>2a</b>–<b>h</b> and acetyl heterocyclic compounds (<b>4</b>, <b>6</b>, <b>8</b>, <b>10</b>, and <b>12</b>) in the presence of cellulose sulfuric acid (CSA) as the green catalyst. These procedures offer an interesting method for the large-scale industrial manufacture of azines due to their high percentage yield, mild reaction conditions, broad substrate range, and utilization of an economical and environmentally acceptable catalyst. Additionally, the molecular docking of the products to the monoamine oxidase (MAO-A) target protein was achieved to highlight the possible binding interaction with the amino acid residues Arg51, Glu43, Gly22, Gly49, Gly443, Ala272, Ile335, and Tyr407 at the point of binding. The binding interaction energy was discovered to be (− 6.48 kcal/mol) for the protein MAO-A (PDB ID: 2Z5X). The most effective azine derivatives <b>7</b> and <b>13</b> revealed some major conserved interactions between the MAO-A protein’s binding site amino acid residues and the PDB co-crystal ligand 2Z5X. Moreover, azine derivatives <b>3a</b> and <b>3f</b> showed the lowest binding activity with the target MAO-A. |
| first_indexed | 2024-03-11T08:58:12Z |
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| language | English |
| last_indexed | 2024-03-11T08:58:12Z |
| publishDate | 2023-02-01 |
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| record_format | Article |
| series | Crystals |
| spelling | doaj.art-b95029c484914cd5a6b158e7ed6268cd2023-11-16T19:55:44ZengMDPI AGCrystals2073-43522023-02-0113226010.3390/cryst13020260Green Route Synthesis and Molecular Docking of Azines Using Cellulose Sulfuric Acid under Microwave IrradiationSobhi M. Gomha0Sayed M. Riyadh1Reem A. K. Alharbi2Magdi E. A. Zaki3Tariq Z. Abolibda4Basant Farag5Department of Chemistry, Faculty of Science, Islamic University of Madinah, Madinah 42351, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Cairo University, Giza 12613, EgyptDepartment of Chemistry, Faculty of Science, Taibah University, Al-Madinah Almunawrah 30002, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh 11623, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Islamic University of Madinah, Madinah 42351, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Zagazig University, Zagazig 44519, EgyptA novel catalytic approach for the synthesis of symmetric and asymmetric azines has been developed. The environmentally benign protocol was achieved via condensation of 1-[(2-thienyl)ethylidene]hydrazine (<b>1</b>) with different aromatic aldehydes <b>2a</b>–<b>h</b> and acetyl heterocyclic compounds (<b>4</b>, <b>6</b>, <b>8</b>, <b>10</b>, and <b>12</b>) in the presence of cellulose sulfuric acid (CSA) as the green catalyst. These procedures offer an interesting method for the large-scale industrial manufacture of azines due to their high percentage yield, mild reaction conditions, broad substrate range, and utilization of an economical and environmentally acceptable catalyst. Additionally, the molecular docking of the products to the monoamine oxidase (MAO-A) target protein was achieved to highlight the possible binding interaction with the amino acid residues Arg51, Glu43, Gly22, Gly49, Gly443, Ala272, Ile335, and Tyr407 at the point of binding. The binding interaction energy was discovered to be (− 6.48 kcal/mol) for the protein MAO-A (PDB ID: 2Z5X). The most effective azine derivatives <b>7</b> and <b>13</b> revealed some major conserved interactions between the MAO-A protein’s binding site amino acid residues and the PDB co-crystal ligand 2Z5X. Moreover, azine derivatives <b>3a</b> and <b>3f</b> showed the lowest binding activity with the target MAO-A.https://www.mdpi.com/2073-4352/13/2/260Schiff basecondensation reactionazinesmolecular dockingMAO-A target protein |
| spellingShingle | Sobhi M. Gomha Sayed M. Riyadh Reem A. K. Alharbi Magdi E. A. Zaki Tariq Z. Abolibda Basant Farag Green Route Synthesis and Molecular Docking of Azines Using Cellulose Sulfuric Acid under Microwave Irradiation Crystals Schiff base condensation reaction azines molecular docking MAO-A target protein |
| title | Green Route Synthesis and Molecular Docking of Azines Using Cellulose Sulfuric Acid under Microwave Irradiation |
| title_full | Green Route Synthesis and Molecular Docking of Azines Using Cellulose Sulfuric Acid under Microwave Irradiation |
| title_fullStr | Green Route Synthesis and Molecular Docking of Azines Using Cellulose Sulfuric Acid under Microwave Irradiation |
| title_full_unstemmed | Green Route Synthesis and Molecular Docking of Azines Using Cellulose Sulfuric Acid under Microwave Irradiation |
| title_short | Green Route Synthesis and Molecular Docking of Azines Using Cellulose Sulfuric Acid under Microwave Irradiation |
| title_sort | green route synthesis and molecular docking of azines using cellulose sulfuric acid under microwave irradiation |
| topic | Schiff base condensation reaction azines molecular docking MAO-A target protein |
| url | https://www.mdpi.com/2073-4352/13/2/260 |
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