Four-Component Synthesis of 1,2-Dihydropyridine Derivatives and their Evaluation as Anticancer Agents

Author(s): Mohamed A. O. Abdel-Fattah, Mahmoud A. M. El-Naggar, Rasha M. H. Rashied, Bernard D. Gary, Gary A. Piazza, Ashraf H. Abadi

Journal Name: Medicinal Chemistry

Volume 8 , Issue 3 , 2012

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Two series of compounds with the general formula of 4,6-diaryl-2-oxo-1,2 dihydropyridine-3-carbonitriles and their isosteric imino derivatives were synthesized through a one pot reaction of acetophenone, aldehyde and ammonium acetate with ethyl cyanoacetate or malononitrile, respectively. The synthesized compounds were evaluated for tumor cell growth inhibitory using the human HT-29 colon and MDA-MB-231 breast tumor cell lines. Compound 4-(2- Ethoxyphenyl)-2-imino-6-(4-fluorophenyl)-1,2-dihydropyridine-3 carbonitrile (6) showed IC50 value of 0.70 μM versus HT-29. Meanwhile, compound 4-(2-Hydroxyphenyl)-2-imino-6-(4-fluorophenyl)-1,2-dihydropyridine-3-carbonitrile (4) showed IC50 value of 4.6 μM versus MDA-MB-231. Docking compound 10 to possible molecular targets, survivin and PIM1 kinase showed appreciable interactions with both, which suggest possible targets for the antitumor activity of this novel class of anticancer compounds.

Keywords: Multicomponent reactions, 1, 2-dihydropyridine, cancer, malononitrile, dihydropyridine, cyanoacetate, acetophenone, isosteric, oxopyridines, antimicrobials

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Article Details

Year: 2012
Page: [392 - 400]
Pages: 9
DOI: 10.2174/1573406411208030392
Price: $65

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