Substituted 4-Acyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazones with Antioxidant Properties: X-Ray Crystal and Spectroscopic Studies
Phenylhydrazine was reacted with synthesized acylpyrazolone derivatives 4-ethyl-5-methyl-2-phenyl-pyrazol-3-one and 4-propyl-5-methyl-2-phenyl-pyrazol-3-one, to obtain two new azomethine phenylhydrazones, a study in continuation of our probe into the effects of acyl group substitutions on the physic...
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| Format: | Article |
| Language: | English |
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Wiley
2017-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2017/7943051 |
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| author | Omoruyi G. Idemudia Anthony I. Okoh Alexander P. Sadimenko Eric C. Hosten Omobola O. Okoh |
| author_facet | Omoruyi G. Idemudia Anthony I. Okoh Alexander P. Sadimenko Eric C. Hosten Omobola O. Okoh |
| author_sort | Omoruyi G. Idemudia |
| collection | DOAJ |
| description | Phenylhydrazine was reacted with synthesized acylpyrazolone derivatives 4-ethyl-5-methyl-2-phenyl-pyrazol-3-one and 4-propyl-5-methyl-2-phenyl-pyrazol-3-one, to obtain two new azomethine phenylhydrazones, a study in continuation of our probe into the effects of acyl group substitutions on the physicochemical and free radical scavenging properties of acylpyrazolone Schiff bases. The keto imine tautomers of 4-ethyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazone (Empp-Ph) and 4-propyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazone (Prmpp-Ph) according to single X-ray crystallography data which precipitated in good yield are reported. Furthermore they have been characterized by elemental analysis, FTIR, 13C and 1H NMR, and mass-spectroscopy techniques. Both phenylhydrazone Schiff bases crystallize in a triclinic crystal system, each with a space group of P-1 (number 2) having short intramolecular N3—H3…O1 hydrogen interaction between the first hydrazine hydrogen H3 and the pyrazolone oxygen O1. The antioxidant free radical scavenging activities of titled compounds against 2,2-diphenyl-1-picrylhydrazyl (DPPH) showed a positive response almost as good as that of vitamin c under the same conditions, with the propyl substituted 4-propyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazone (Prmpp-Ph) having a stronger activity (calculated IC50 value of 175.66 μg/ml). |
| format | Article |
| id | doaj-art-9ed17effc63a41f1a95626e0fb565fb2 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2017-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-9ed17effc63a41f1a95626e0fb565fb22025-02-03T00:59:52ZengWileyJournal of Chemistry2090-90632090-90712017-01-01201710.1155/2017/79430517943051Substituted 4-Acyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazones with Antioxidant Properties: X-Ray Crystal and Spectroscopic StudiesOmoruyi G. Idemudia0Anthony I. Okoh1Alexander P. Sadimenko2Eric C. Hosten3Omobola O. Okoh4Chemistry Department, University of Fort Hare, Private Bag x1314, Alice 5700, South AfricaSAMRC, Microbial Water Quality Monitoring Centre, University of Fort Hare, Alice 5700, South AfricaChemistry Department, University of Fort Hare, Private Bag x1314, Alice 5700, South AfricaChemistry Department, Nelson Mandela Metropolitan University, P.O. Box 77000, Port Elizabeth 6031, South AfricaChemistry Department, University of Fort Hare, Private Bag x1314, Alice 5700, South AfricaPhenylhydrazine was reacted with synthesized acylpyrazolone derivatives 4-ethyl-5-methyl-2-phenyl-pyrazol-3-one and 4-propyl-5-methyl-2-phenyl-pyrazol-3-one, to obtain two new azomethine phenylhydrazones, a study in continuation of our probe into the effects of acyl group substitutions on the physicochemical and free radical scavenging properties of acylpyrazolone Schiff bases. The keto imine tautomers of 4-ethyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazone (Empp-Ph) and 4-propyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazone (Prmpp-Ph) according to single X-ray crystallography data which precipitated in good yield are reported. Furthermore they have been characterized by elemental analysis, FTIR, 13C and 1H NMR, and mass-spectroscopy techniques. Both phenylhydrazone Schiff bases crystallize in a triclinic crystal system, each with a space group of P-1 (number 2) having short intramolecular N3—H3…O1 hydrogen interaction between the first hydrazine hydrogen H3 and the pyrazolone oxygen O1. The antioxidant free radical scavenging activities of titled compounds against 2,2-diphenyl-1-picrylhydrazyl (DPPH) showed a positive response almost as good as that of vitamin c under the same conditions, with the propyl substituted 4-propyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazone (Prmpp-Ph) having a stronger activity (calculated IC50 value of 175.66 μg/ml).http://dx.doi.org/10.1155/2017/7943051 |
| spellingShingle | Omoruyi G. Idemudia Anthony I. Okoh Alexander P. Sadimenko Eric C. Hosten Omobola O. Okoh Substituted 4-Acyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazones with Antioxidant Properties: X-Ray Crystal and Spectroscopic Studies Journal of Chemistry |
| title | Substituted 4-Acyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazones with Antioxidant Properties: X-Ray Crystal and Spectroscopic Studies |
| title_full | Substituted 4-Acyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazones with Antioxidant Properties: X-Ray Crystal and Spectroscopic Studies |
| title_fullStr | Substituted 4-Acyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazones with Antioxidant Properties: X-Ray Crystal and Spectroscopic Studies |
| title_full_unstemmed | Substituted 4-Acyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazones with Antioxidant Properties: X-Ray Crystal and Spectroscopic Studies |
| title_short | Substituted 4-Acyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazones with Antioxidant Properties: X-Ray Crystal and Spectroscopic Studies |
| title_sort | substituted 4 acyl 5 methyl 2 phenyl pyrazol 3 one phenylhydrazones with antioxidant properties x ray crystal and spectroscopic studies |
| url | http://dx.doi.org/10.1155/2017/7943051 |
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