Conformational profile, vibrational assignments, NLO properties and molecular docking of biologically active herbicide1,1-dimethyl-3-phenylurea
1,1-Dimethyl-3-phenylurea (known as fenuron) which is a phenyl urea-based widely used herbicide exhibits interesting structural and conformational properties and a notable biological activity. A detailed analysis on the vibrational, molecular and electronic characteristics of fenuron has been carrie...
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| Format: | Article |
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Elsevier
2019-06-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844019356129 |
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| author | K. Haruna Veena S. Kumar Y. Sheena Mary S.A. Popoola Renjith Thomas M.S. Roxy A.A. Al-Saadi |
| author_facet | K. Haruna Veena S. Kumar Y. Sheena Mary S.A. Popoola Renjith Thomas M.S. Roxy A.A. Al-Saadi |
| author_sort | K. Haruna |
| collection | DOAJ |
| description | 1,1-Dimethyl-3-phenylurea (known as fenuron) which is a phenyl urea-based widely used herbicide exhibits interesting structural and conformational properties and a notable biological activity. A detailed analysis on the vibrational, molecular and electronic characteristics of fenuron has been carried out. Potential energy scans (PESs) performed at the B3LYP/6-311++G(d,p) level of theory predicted two possible minima corresponding to the optimized anti and synforms resulting from the internal rotation about the N-C bond. The presence of an auxochrome together with the interaction with DMSO solvent exhibited a blue shift corresponding to the C=O orbitals. Delocalization of HOMO and LUMO orbital facilitated the charge transfer effect in the molecule. The calculated HOMO-LUMO energies, chemical potential, energy gap and global hardness suggested a low softness value for the compound while its biological activity was described by the value of electrophilicity. Chlorine substitution in the phenyl ring influenced the orbital delocalization for ortho and para substitutions but that of meta remained unaffected. NLO properties were noticed to increase due to chlorine substitution in the parent molecule. The docking results suggested that the compound exhibits an inhibitory activity against mitochondrial ubiquinol-cytochrome-c reductase and can be developed as a potential anticancer agent. |
| first_indexed | 2024-12-16T11:55:59Z |
| format | Article |
| id | doaj.art-c2ac1449f108425bab91a1cdd487523d |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-12-16T11:55:59Z |
| publishDate | 2019-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-c2ac1449f108425bab91a1cdd487523d2022-12-21T22:32:33ZengElsevierHeliyon2405-84402019-06-0156e01987Conformational profile, vibrational assignments, NLO properties and molecular docking of biologically active herbicide1,1-dimethyl-3-phenylureaK. Haruna0Veena S. Kumar1Y. Sheena Mary2S.A. Popoola3Renjith Thomas4M.S. Roxy5A.A. Al-Saadi6Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, Saudi ArabiaDepartment of Physics, SN College, Kollam, Kerala, IndiaDepartment of Physics, Fatima Mata National College(Autonomous), Kollam, Kerala, India; Corresponding author.Department of Chemistry, Islamic University of Madinah, MadinahMunawara, Saudi ArabiaDepartment of Chemistry, St. Berchmans College (Autonomous), Changanacherry, Kerala, IndiaDepartment of Physics, SN College, Kollam, Kerala, IndiaDepartment of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia; Corresponding author.1,1-Dimethyl-3-phenylurea (known as fenuron) which is a phenyl urea-based widely used herbicide exhibits interesting structural and conformational properties and a notable biological activity. A detailed analysis on the vibrational, molecular and electronic characteristics of fenuron has been carried out. Potential energy scans (PESs) performed at the B3LYP/6-311++G(d,p) level of theory predicted two possible minima corresponding to the optimized anti and synforms resulting from the internal rotation about the N-C bond. The presence of an auxochrome together with the interaction with DMSO solvent exhibited a blue shift corresponding to the C=O orbitals. Delocalization of HOMO and LUMO orbital facilitated the charge transfer effect in the molecule. The calculated HOMO-LUMO energies, chemical potential, energy gap and global hardness suggested a low softness value for the compound while its biological activity was described by the value of electrophilicity. Chlorine substitution in the phenyl ring influenced the orbital delocalization for ortho and para substitutions but that of meta remained unaffected. NLO properties were noticed to increase due to chlorine substitution in the parent molecule. The docking results suggested that the compound exhibits an inhibitory activity against mitochondrial ubiquinol-cytochrome-c reductase and can be developed as a potential anticancer agent.http://www.sciencedirect.com/science/article/pii/S2405844019356129Organic chemistryPharmaceutical chemistryTheoretical chemistryDFTFenuronMolecular docking |
| spellingShingle | K. Haruna Veena S. Kumar Y. Sheena Mary S.A. Popoola Renjith Thomas M.S. Roxy A.A. Al-Saadi Conformational profile, vibrational assignments, NLO properties and molecular docking of biologically active herbicide1,1-dimethyl-3-phenylurea Heliyon Organic chemistry Pharmaceutical chemistry Theoretical chemistry DFT Fenuron Molecular docking |
| title | Conformational profile, vibrational assignments, NLO properties and molecular docking of biologically active herbicide1,1-dimethyl-3-phenylurea |
| title_full | Conformational profile, vibrational assignments, NLO properties and molecular docking of biologically active herbicide1,1-dimethyl-3-phenylurea |
| title_fullStr | Conformational profile, vibrational assignments, NLO properties and molecular docking of biologically active herbicide1,1-dimethyl-3-phenylurea |
| title_full_unstemmed | Conformational profile, vibrational assignments, NLO properties and molecular docking of biologically active herbicide1,1-dimethyl-3-phenylurea |
| title_short | Conformational profile, vibrational assignments, NLO properties and molecular docking of biologically active herbicide1,1-dimethyl-3-phenylurea |
| title_sort | conformational profile vibrational assignments nlo properties and molecular docking of biologically active herbicide1 1 dimethyl 3 phenylurea |
| topic | Organic chemistry Pharmaceutical chemistry Theoretical chemistry DFT Fenuron Molecular docking |
| url | http://www.sciencedirect.com/science/article/pii/S2405844019356129 |
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