Phthalazine based hydrazone as potent radical scavenger: Synthesis, spectral characterization, single crystal X-ray diffraction, DFT studies, molecular docking, ADME, antioxidant and antimicrobial activity of (E)-1-(2-substitutedbenzylidene)phthalazine derivatives
This study examines the synthesis, structural and biological properties of phthalazine-derived hydrazone compounds. A series of hydrazone derivatives based on phthalazine (1a-h) were synthesized. FT-IR, 1H & 13C NMR, and Mass spectrometry were used to determine their structures, while Single...
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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/S2211715624006544 |
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| author | Surya Uthrapathy Balasankar Thirunavukkarasu Kodisundaram Paulrasu Tanzeer Ahmad Dar Manikandan Palrasu Morris Princey Krishnapriya Thangaretnam Vinoth Murali |
| author_facet | Surya Uthrapathy Balasankar Thirunavukkarasu Kodisundaram Paulrasu Tanzeer Ahmad Dar Manikandan Palrasu Morris Princey Krishnapriya Thangaretnam Vinoth Murali |
| author_sort | Surya Uthrapathy |
| collection | DOAJ |
| description | This study examines the synthesis, structural and biological properties of phthalazine-derived hydrazone compounds. A series of hydrazone derivatives based on phthalazine (1a-h) were synthesized. FT-IR, 1H & 13C NMR, and Mass spectrometry were used to determine their structures, while Single crystal X-ray diffraction studies identified the hydrazone tautomer. Computational studies employing density functional theory (DFT) indicated that the compounds exhibited an E-configuration about the hydrazone linkage and provided insights into the chemical reactivity and stability through FMO energies and Mulliken charge analysis. Theoretical bond parameters obtained via DFT analysis closely match the experimental data, further validating the confirmation of the synthesized compound. Molecular docking studies conducted with AutoDock 4.0, revealed docking scores from −4.87 to −7.62 kcal/mol when interacting with cytochrome C peroxidase (2X08) and E.coli reductase (1YLU) proteins highlighting potential bioactive interactions. Based on their docking scores, the synthesized compounds (1a-h) were further evaluated through In-vitro antibacterial and antioxidant assays. The results indicated that compounds with electron-donating substituents exhibit better antioxidant properties. In contrast, compounds containing electron-withdrawing groups show greater antibacterial activity. These findings suggest the potential therapeutic applications of these compounds, with distinct activities based on their electronic properties. |
| format | Article |
| id | doaj-art-a09b8799a8b9442fa092047d3cb71905 |
| institution | Kabale University |
| issn | 2211-7156 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj-art-a09b8799a8b9442fa092047d3cb719052025-01-29T05:00:41ZengElsevierResults in Chemistry2211-71562025-01-0113101958Phthalazine based hydrazone as potent radical scavenger: Synthesis, spectral characterization, single crystal X-ray diffraction, DFT studies, molecular docking, ADME, antioxidant and antimicrobial activity of (E)-1-(2-substitutedbenzylidene)phthalazine derivativesSurya Uthrapathy0Balasankar Thirunavukkarasu1Kodisundaram Paulrasu2Tanzeer Ahmad Dar3Manikandan Palrasu4Morris Princey5Krishnapriya Thangaretnam6Vinoth Murali7Department of Chemistry, Annamalai University, Annamalai Nagar, 608002, Tamilnadu, IndiaChemistry Section, FEAT, Annamalai University, Annamalai Nagar, 608002, Tamilnadu, India; Corresponding author.Department of Chemistry, Annamalai University, Annamalai Nagar, 608002, Tamilnadu, India; Department of Surgery, Miller school of Medicine, University of Miami, FL 33136Department of Chemistry, Annamalai University, Annamalai Nagar, 608002, Tamilnadu, IndiaUniversity of South Carlino, School of Medicine, SC 29209, USADepartment of Chemistry, Holy Cross College, Tiruchirapalli, Tamilnadu, IndiaDepartment of Surgery, Miller school of Medicine, University of Miami, FL 33136Department of Chemistry, IFET College of Engineering (Autonomous), Villupuram, Tamil Nadu, IndiaThis study examines the synthesis, structural and biological properties of phthalazine-derived hydrazone compounds. A series of hydrazone derivatives based on phthalazine (1a-h) were synthesized. FT-IR, 1H & 13C NMR, and Mass spectrometry were used to determine their structures, while Single crystal X-ray diffraction studies identified the hydrazone tautomer. Computational studies employing density functional theory (DFT) indicated that the compounds exhibited an E-configuration about the hydrazone linkage and provided insights into the chemical reactivity and stability through FMO energies and Mulliken charge analysis. Theoretical bond parameters obtained via DFT analysis closely match the experimental data, further validating the confirmation of the synthesized compound. Molecular docking studies conducted with AutoDock 4.0, revealed docking scores from −4.87 to −7.62 kcal/mol when interacting with cytochrome C peroxidase (2X08) and E.coli reductase (1YLU) proteins highlighting potential bioactive interactions. Based on their docking scores, the synthesized compounds (1a-h) were further evaluated through In-vitro antibacterial and antioxidant assays. The results indicated that compounds with electron-donating substituents exhibit better antioxidant properties. In contrast, compounds containing electron-withdrawing groups show greater antibacterial activity. These findings suggest the potential therapeutic applications of these compounds, with distinct activities based on their electronic properties.http://www.sciencedirect.com/science/article/pii/S2211715624006544Phthalazine-derived HydrazoneHydrazone TautomerDFTAntioxidantAntibacterialADME |
| spellingShingle | Surya Uthrapathy Balasankar Thirunavukkarasu Kodisundaram Paulrasu Tanzeer Ahmad Dar Manikandan Palrasu Morris Princey Krishnapriya Thangaretnam Vinoth Murali Phthalazine based hydrazone as potent radical scavenger: Synthesis, spectral characterization, single crystal X-ray diffraction, DFT studies, molecular docking, ADME, antioxidant and antimicrobial activity of (E)-1-(2-substitutedbenzylidene)phthalazine derivatives Results in Chemistry Phthalazine-derived Hydrazone Hydrazone Tautomer DFT Antioxidant Antibacterial ADME |
| title | Phthalazine based hydrazone as potent radical scavenger: Synthesis, spectral characterization, single crystal X-ray diffraction, DFT studies, molecular docking, ADME, antioxidant and antimicrobial activity of (E)-1-(2-substitutedbenzylidene)phthalazine derivatives |
| title_full | Phthalazine based hydrazone as potent radical scavenger: Synthesis, spectral characterization, single crystal X-ray diffraction, DFT studies, molecular docking, ADME, antioxidant and antimicrobial activity of (E)-1-(2-substitutedbenzylidene)phthalazine derivatives |
| title_fullStr | Phthalazine based hydrazone as potent radical scavenger: Synthesis, spectral characterization, single crystal X-ray diffraction, DFT studies, molecular docking, ADME, antioxidant and antimicrobial activity of (E)-1-(2-substitutedbenzylidene)phthalazine derivatives |
| title_full_unstemmed | Phthalazine based hydrazone as potent radical scavenger: Synthesis, spectral characterization, single crystal X-ray diffraction, DFT studies, molecular docking, ADME, antioxidant and antimicrobial activity of (E)-1-(2-substitutedbenzylidene)phthalazine derivatives |
| title_short | Phthalazine based hydrazone as potent radical scavenger: Synthesis, spectral characterization, single crystal X-ray diffraction, DFT studies, molecular docking, ADME, antioxidant and antimicrobial activity of (E)-1-(2-substitutedbenzylidene)phthalazine derivatives |
| title_sort | phthalazine based hydrazone as potent radical scavenger synthesis spectral characterization single crystal x ray diffraction dft studies molecular docking adme antioxidant and antimicrobial activity of e 1 2 substitutedbenzylidene phthalazine derivatives |
| topic | Phthalazine-derived Hydrazone Hydrazone Tautomer DFT Antioxidant Antibacterial ADME |
| url | http://www.sciencedirect.com/science/article/pii/S2211715624006544 |
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