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Keywords = 4-amino-2,5-dimethyl-1-phenyl-3-oxo-1H-pyrazolone

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15 pages, 353 KB  
Article
Synthesis, Characterization and Anti-Breast Cancer Activity of New 4-Aminoantipyrine-Based Heterocycles
by Mostafa M. Ghorab, Marwa G. El-Gazzar and Mansour S. Alsaid
Int. J. Mol. Sci. 2014, 15(5), 7539-7553; https://doi.org/10.3390/ijms15057539 - 2 May 2014
Cited by 63 | Viewed by 8160
Abstract
4-Aminoantipyrine was utilized as key intermediate for the synthesis of pyrazolone derivatives bearing biologically active moieties. The newly synthesized compounds were characterized by IR, 1H- and 13C-NMR spectral and microanalytical studies. The compounds were screened as anticancer agents against a human [...] Read more.
4-Aminoantipyrine was utilized as key intermediate for the synthesis of pyrazolone derivatives bearing biologically active moieties. The newly synthesized compounds were characterized by IR, 1H- and 13C-NMR spectral and microanalytical studies. The compounds were screened as anticancer agents against a human tumor breast cancer cell line MCF7, and the results showed that (Z)-4-((3-amino-5-imino-1-phenyl-1H-pyrazol-4(5H)-ylidene)methylamino)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one 5, 3-(4-bromophenyl) -1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 13, 1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-3-(4-iodophenyl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 14, 3,3′-(4,4′-sulfonylbis(4,1-phenylene))bis(1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile) 16, (Z)-1- (1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-hydrazono-4-oxo-3-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 17, (Z)-1-(1,5-dimethyl-3-oxo-2-phenyl- 2,3-dihydro-1H-pyrazol-4-yl)-4-oxo-3-phenyl-2-(2-phenylhydrazono)-1,2,3,4-tetrahydro pyrimidine-5-carbonitrile 18, and (Z)-4-(3-amino-6-hydrazono-7-phenyl-6,7-dihydro pyrazolo[3,4-d]pyrimidin-5-yl)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one 19 were the most active compounds with IC50 values ranging from 30.68 to 60.72 µM compared with Doxorubicin as positive control with the IC50 value 71.8 µM. Full article
(This article belongs to the Special Issue Molecular Science for Drug Development and Biomedicine)
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3 pages, 274 KB  
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N,N’-Bis-(2,5-dimethyl-3-oxo-1-phenyl-2,3-dihydro-1H-pyrazol-4-yl)phthalamide
by Fatma Aydin and Erdoğan Dağci
Molbank 2012, 2012(2), M754; https://doi.org/10.3390/M754 - 18 Apr 2012
Viewed by 4024
Abstract
The title compound, N,N’-bis-(2,5-dimethyl-3-oxo-1-phenyl-2,3-dihydro-1H-pyrazol-4-yl)phthalamide has been synthesized by reactions of o-phthaloyl chloride with 4-amino-2,5-dimethyl-1-phenyl-3-oxo-1H-pyrazolone in acetonitrile. The structure of the new compound was characterized by FT-IR, 1H NMR, 13C NMR and mass spectroscopic techniques. Physical [...] Read more.
The title compound, N,N’-bis-(2,5-dimethyl-3-oxo-1-phenyl-2,3-dihydro-1H-pyrazol-4-yl)phthalamide has been synthesized by reactions of o-phthaloyl chloride with 4-amino-2,5-dimethyl-1-phenyl-3-oxo-1H-pyrazolone in acetonitrile. The structure of the new compound was characterized by FT-IR, 1H NMR, 13C NMR and mass spectroscopic techniques. Physical parameters of the compound such as melting point, solubility, λmax were examined. Full article
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