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Article

Synthesis, Characterization and Anti-Breast Cancer Activity of New 4-Aminoantipyrine-Based Heterocycles

1
Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
2
Department of Drug Radiation Research, National Center for Radiation Research and Technology, Nasr City, Cairo 113701, Egypt
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2014, 15(5), 7539-7553; https://doi.org/10.3390/ijms15057539
Received: 19 March 2014 / Revised: 9 April 2014 / Accepted: 17 April 2014 / Published: 2 May 2014
(This article belongs to the Special Issue Molecular Science for Drug Development and Biomedicine)
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. View Full-Text
Keywords: pyrazoles; sulfonamides; anti-breast cancer pyrazoles; sulfonamides; anti-breast cancer
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MDPI and ACS Style

Ghorab, M.M.; El-Gazzar, M.G.; Alsaid, M.S. Synthesis, Characterization and Anti-Breast Cancer Activity of New 4-Aminoantipyrine-Based Heterocycles. Int. J. Mol. Sci. 2014, 15, 7539-7553. https://doi.org/10.3390/ijms15057539

AMA Style

Ghorab MM, El-Gazzar MG, Alsaid MS. Synthesis, Characterization and Anti-Breast Cancer Activity of New 4-Aminoantipyrine-Based Heterocycles. International Journal of Molecular Sciences. 2014; 15(5):7539-7553. https://doi.org/10.3390/ijms15057539

Chicago/Turabian Style

Ghorab, Mostafa M., Marwa G. El-Gazzar, and Mansour S. Alsaid. 2014. "Synthesis, Characterization and Anti-Breast Cancer Activity of New 4-Aminoantipyrine-Based Heterocycles" International Journal of Molecular Sciences 15, no. 5: 7539-7553. https://doi.org/10.3390/ijms15057539

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