Because of the reported anticancer activity of quinolines and pyrimidoquinolines containing the biologically active sulfonamide moiety, a new series of quinoline and pyrimidoquinoline derivatives were synthesized and tested for in-vitro anticancer activity against liver-cancer cells. Reaction of 5,5-dimethylcyclohexane-1,3-dione 1 with sulfanilamide 2 in ethanol yielded the corresponding enaminone 3. Treatment of enaminone 3 with 2-(4-methylbenzylidene)malononitrile 4 gave the corresponding strategic starting material quinoline 6. The quinoline-o-aminocarbonitrile 6 was used to synthesize new series of quinolines 8, 11, 15–20 and pyrimidoquinolines 7, 10, 12–14. The structures of the synthesized compounds were confirmed by microanalysis, IR, 1H NMR, and 13C NMR spectroscopy, and use of mass spectral data. Almost all the compounds had significant activity against human cancer cell line HEPG2 compared with doxorubicin as a positive control. The most potent compounds, 7, 10, and 20, were also evaluated for their ability to enhance the killing effect of γ-radiation.
Research on Chemical Intermediates – Springer Journals
Published: May 8, 2013
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