Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies
Polytopic organic ligands with hydrazone moiety are at the forefront of new drug research among many others due to their unique and versatile functionality and ease of strategic ligand design. Quantum chemical calculations of these polyfunctional ligands can be carried out in silico to determine the...
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MDPI AG
2022-03-01
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| Online Access: | https://www.mdpi.com/1420-3049/27/5/1656 |
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| author | Sharmin Akther Rupa Md. Rassel Moni Md. Abdul Majed Patwary Md. Mayez Mahmud Md. Aminul Haque Jamal Uddin S. M. Tareque Abedin |
| author_facet | Sharmin Akther Rupa Md. Rassel Moni Md. Abdul Majed Patwary Md. Mayez Mahmud Md. Aminul Haque Jamal Uddin S. M. Tareque Abedin |
| author_sort | Sharmin Akther Rupa |
| collection | DOAJ |
| description | Polytopic organic ligands with hydrazone moiety are at the forefront of new drug research among many others due to their unique and versatile functionality and ease of strategic ligand design. Quantum chemical calculations of these polyfunctional ligands can be carried out in silico to determine the thermodynamic parameters. In this study two new tritopic dihydrazide ligands, N’2, N’6-bis[(1<i>E</i>)-1-(thiophen-2-yl) ethylidene] pyridine-2,6-dicarbohydrazide (L1) and N’2, N’6-bis[(1<i>E</i>)-1-(1H-pyrrol-2-yl) ethylidene] pyridine-2,6-dicarbohydrazide (L2) were successfully prepared by the condensation reaction of pyridine-2,6-dicarboxylic hydrazide with 2-acetylthiophene and 2-acetylpyrrole. The FT-IR, <sup>1</sup>H, and <sup>13</sup>C NMR, as well as mass spectra of both L1 and L2, were recorded and analyzed. Quantum chemical calculations were performed at the DFT/B3LYP/cc-pvdz/6-311G+(d,p) level of theory to study the molecular geometry, vibrational frequencies, and thermodynamic properties including changes of <i>∆H</i>, <i>∆S,</i> and <i>∆G</i> for both the ligands. The optimized vibrational frequency and (<sup>1</sup>H and <sup>13</sup>C) NMR obtained by B3LYP/cc-pvdz/6-311G+(d,p) showed good agreement with experimental FT-IR and NMR data. Frontier molecular orbital (FMO) calculations were also conducted to find the HOMO, LUMO, and HOMO–LUMO gaps of the two synthesized compounds. To investigate the biological activities of the ligands, L1 and L2 were tested using in vitro bioassays against some Gram-negative and Gram-positive bacteria and fungus strains. In addition, molecular docking was used to study the molecular behavior of L1 and L2 against tyrosinase from <i>Bacillus megaterium.</i> The outcomes revealed that both L1 and L2 can suppress microbial growth of bacteria and fungi with variable potency. The antibacterial activity results demonstrated the compound L2 to be potentially effective against <i>Bacillus</i> <i>megaterium</i> with inhibition zones of 12 mm while the molecular docking study showed the binding energies for L1 and L2 to be −7.7 and −8.8 kcal mol<sup>−1</sup>, respectively, with tyrosinase from <i>Bacillus megaterium.</i> |
| first_indexed | 2024-03-09T20:29:40Z |
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| last_indexed | 2024-03-09T20:29:40Z |
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| spelling | doaj.art-f66c174b9afb4d8aa791c889d1fa58532023-11-23T23:27:45ZengMDPI AGMolecules1420-30492022-03-01275165610.3390/molecules27051656Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking StudiesSharmin Akther Rupa0Md. Rassel Moni1Md. Abdul Majed Patwary2Md. Mayez Mahmud3Md. Aminul Haque4Jamal Uddin5S. M. Tareque Abedin6Department of Chemistry, Comilla University, Cumilla 3506, BangladeshDepartment of Chemistry, Comilla University, Cumilla 3506, BangladeshDepartment of Chemistry, Comilla University, Cumilla 3506, BangladeshFaculty of Pharmaceutical Science, Tokushima University, Tokushima Shi 770-0026, JapanDepartment of Chemistry, Jagannath University, Dhaka 1100, BangladeshDepartment of Natural Sciences, Center for Nanotechnology, Coppin State University, Baltimore, MD 21216, USADepartment of Chemistry, Jahangirnagar University, Savar 1342, BangladeshPolytopic organic ligands with hydrazone moiety are at the forefront of new drug research among many others due to their unique and versatile functionality and ease of strategic ligand design. Quantum chemical calculations of these polyfunctional ligands can be carried out in silico to determine the thermodynamic parameters. In this study two new tritopic dihydrazide ligands, N’2, N’6-bis[(1<i>E</i>)-1-(thiophen-2-yl) ethylidene] pyridine-2,6-dicarbohydrazide (L1) and N’2, N’6-bis[(1<i>E</i>)-1-(1H-pyrrol-2-yl) ethylidene] pyridine-2,6-dicarbohydrazide (L2) were successfully prepared by the condensation reaction of pyridine-2,6-dicarboxylic hydrazide with 2-acetylthiophene and 2-acetylpyrrole. The FT-IR, <sup>1</sup>H, and <sup>13</sup>C NMR, as well as mass spectra of both L1 and L2, were recorded and analyzed. Quantum chemical calculations were performed at the DFT/B3LYP/cc-pvdz/6-311G+(d,p) level of theory to study the molecular geometry, vibrational frequencies, and thermodynamic properties including changes of <i>∆H</i>, <i>∆S,</i> and <i>∆G</i> for both the ligands. The optimized vibrational frequency and (<sup>1</sup>H and <sup>13</sup>C) NMR obtained by B3LYP/cc-pvdz/6-311G+(d,p) showed good agreement with experimental FT-IR and NMR data. Frontier molecular orbital (FMO) calculations were also conducted to find the HOMO, LUMO, and HOMO–LUMO gaps of the two synthesized compounds. To investigate the biological activities of the ligands, L1 and L2 were tested using in vitro bioassays against some Gram-negative and Gram-positive bacteria and fungus strains. In addition, molecular docking was used to study the molecular behavior of L1 and L2 against tyrosinase from <i>Bacillus megaterium.</i> The outcomes revealed that both L1 and L2 can suppress microbial growth of bacteria and fungi with variable potency. The antibacterial activity results demonstrated the compound L2 to be potentially effective against <i>Bacillus</i> <i>megaterium</i> with inhibition zones of 12 mm while the molecular docking study showed the binding energies for L1 and L2 to be −7.7 and −8.8 kcal mol<sup>−1</sup>, respectively, with tyrosinase from <i>Bacillus megaterium.</i>https://www.mdpi.com/1420-3049/27/5/1656DFTvibrational frequenciesFMOtritopicpolydentatemolecular docking |
| spellingShingle | Sharmin Akther Rupa Md. Rassel Moni Md. Abdul Majed Patwary Md. Mayez Mahmud Md. Aminul Haque Jamal Uddin S. M. Tareque Abedin Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies Molecules DFT vibrational frequencies FMO tritopic polydentate molecular docking |
| title | Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies |
| title_full | Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies |
| title_fullStr | Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies |
| title_full_unstemmed | Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies |
| title_short | Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies |
| title_sort | synthesis of novel tritopic hydrazone ligands spectroscopy biological activity dft and molecular docking studies |
| topic | DFT vibrational frequencies FMO tritopic polydentate molecular docking |
| url | https://www.mdpi.com/1420-3049/27/5/1656 |
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