Synthesis, Characterization, and Biological Activity of N′-[(Z)-(3-Methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide and Its Co(II), Ni(II), and Cu(II) Complexes
Reaction of 1-phenyl-3-methyl-4-benzoyl-pyrazol-5-one and benzoyl hydrazide in refluxing ethanol gave N′-[(Z)-(3-methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide (HL1), which was characterized by NMR spectroscopy and single-crystal X-ray structure study. X-ray dif...
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| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2014-01-01
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| Series: | Bioinorganic Chemistry and Applications |
| Online Access: | http://dx.doi.org/10.1155/2014/718175 |
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| author | Jonnie N. Asegbeloyin Oguejiofo T. Ujam Emmanuel C. Okafor Ilknur Babahan Esin Poyrazoglu Coban Ali Özmen Halil Biyik |
| author_facet | Jonnie N. Asegbeloyin Oguejiofo T. Ujam Emmanuel C. Okafor Ilknur Babahan Esin Poyrazoglu Coban Ali Özmen Halil Biyik |
| author_sort | Jonnie N. Asegbeloyin |
| collection | DOAJ |
| description | Reaction of 1-phenyl-3-methyl-4-benzoyl-pyrazol-5-one and benzoyl hydrazide in refluxing ethanol gave N′-[(Z)-(3-methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide (HL1), which was characterized by NMR spectroscopy and single-crystal X-ray structure study. X-ray diffraction analyses of the crystals revealed a nonplanar molecule, existing in the keto-amine form, with intermolecular hydrogen bonding forming a seven-membered ring system. The reaction of HL1 with Co(II), Ni(II), and Cu(II) halides gave the corresponding complexes, which were characterized by elemental analysis, molar conductance, magnetic measurements, and infrared and electronic spectral studies. The compounds were screened for their in vitro cytotoxic activity against HL-60 human promyelocytic leukemia cells and antimicrobial activity against some bacteria and yeasts. Results showed that the compounds are potent against HL-60 cells with the IC50 value ≤5 μM, while some of the compounds were active against few studied Gram-positive bacteria. |
| format | Article |
| id | doaj-art-e75f0395632646cf8dd7d49a069ed47e |
| institution | Kabale University |
| issn | 1565-3633 1687-479X |
| language | English |
| publishDate | 2014-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Bioinorganic Chemistry and Applications |
| spelling | doaj-art-e75f0395632646cf8dd7d49a069ed47e2025-02-03T05:50:13ZengWileyBioinorganic Chemistry and Applications1565-36331687-479X2014-01-01201410.1155/2014/718175718175Synthesis, Characterization, and Biological Activity of N′-[(Z)-(3-Methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide and Its Co(II), Ni(II), and Cu(II) ComplexesJonnie N. Asegbeloyin0Oguejiofo T. Ujam1Emmanuel C. Okafor2Ilknur Babahan3Esin Poyrazoglu Coban4Ali Özmen5Halil Biyik6Department of Pure and Industrial Chemistry, University of Nigeria, Enugu State, Nsukka 410001, Enugu State, NigeriaDepartment of Pure and Industrial Chemistry, University of Nigeria, Enugu State, Nsukka 410001, Enugu State, NigeriaDepartment of Pure and Industrial Chemistry, University of Nigeria, Enugu State, Nsukka 410001, Enugu State, NigeriaDepartment of Chemistry, Adnan Menderes University, 09010 Aydin, TurkeyDepartment of Biology, Adnan Menderes University, 09010 Aydin, TurkeyDepartment of Biology, Adnan Menderes University, 09010 Aydin, TurkeyDepartment of Biology, Adnan Menderes University, 09010 Aydin, TurkeyReaction of 1-phenyl-3-methyl-4-benzoyl-pyrazol-5-one and benzoyl hydrazide in refluxing ethanol gave N′-[(Z)-(3-methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide (HL1), which was characterized by NMR spectroscopy and single-crystal X-ray structure study. X-ray diffraction analyses of the crystals revealed a nonplanar molecule, existing in the keto-amine form, with intermolecular hydrogen bonding forming a seven-membered ring system. The reaction of HL1 with Co(II), Ni(II), and Cu(II) halides gave the corresponding complexes, which were characterized by elemental analysis, molar conductance, magnetic measurements, and infrared and electronic spectral studies. The compounds were screened for their in vitro cytotoxic activity against HL-60 human promyelocytic leukemia cells and antimicrobial activity against some bacteria and yeasts. Results showed that the compounds are potent against HL-60 cells with the IC50 value ≤5 μM, while some of the compounds were active against few studied Gram-positive bacteria.http://dx.doi.org/10.1155/2014/718175 |
| spellingShingle | Jonnie N. Asegbeloyin Oguejiofo T. Ujam Emmanuel C. Okafor Ilknur Babahan Esin Poyrazoglu Coban Ali Özmen Halil Biyik Synthesis, Characterization, and Biological Activity of N′-[(Z)-(3-Methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide and Its Co(II), Ni(II), and Cu(II) Complexes Bioinorganic Chemistry and Applications |
| title | Synthesis, Characterization, and Biological Activity of N′-[(Z)-(3-Methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide and Its Co(II), Ni(II), and Cu(II) Complexes |
| title_full | Synthesis, Characterization, and Biological Activity of N′-[(Z)-(3-Methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide and Its Co(II), Ni(II), and Cu(II) Complexes |
| title_fullStr | Synthesis, Characterization, and Biological Activity of N′-[(Z)-(3-Methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide and Its Co(II), Ni(II), and Cu(II) Complexes |
| title_full_unstemmed | Synthesis, Characterization, and Biological Activity of N′-[(Z)-(3-Methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide and Its Co(II), Ni(II), and Cu(II) Complexes |
| title_short | Synthesis, Characterization, and Biological Activity of N′-[(Z)-(3-Methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide and Its Co(II), Ni(II), and Cu(II) Complexes |
| title_sort | synthesis characterization and biological activity of n z 3 methyl 5 oxo 1 phenyl 1 5 dihydro 4h pyrazol 4 ylidene phenyl methyl benzohydrazide and its co ii ni ii and cu ii complexes |
| url | http://dx.doi.org/10.1155/2014/718175 |
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