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Anticancer and radiosensitizing evaluation of novel sulfonamides with quinoline and pyrimidoquinoline groups

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Abstract

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.

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Authors and Affiliations

  1. Medicinal, Aromatic and Poisonous Plants Research Center (MAPPRC), College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh, 11451, Saudi Arabia

    Mostafa M. Ghorab

  2. Department of Organic Chemistry, Faculty of Pharmacy, Cairo University, Giza, Cairo, Egypt

    Mohamed A. Shaaban & Ashraf Zaher

  3. Department of Drug Radiation Research, National Center for Radiation Research and Technology, Nasr City, Cairo, Egypt

    Mostafa M. Ghorab, Helmy I. Heiba & Amal A. Hamed

Authors
  1. Mostafa M. Ghorab
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  2. Mohamed A. Shaaban
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  3. Helmy I. Heiba
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  4. Ashraf Zaher
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  5. Amal A. Hamed
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Correspondence to Mostafa M. Ghorab.

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Ghorab, M.M., Shaaban, M.A., Heiba, H.I. et al. Anticancer and radiosensitizing evaluation of novel sulfonamides with quinoline and pyrimidoquinoline groups. Res Chem Intermed 41, 647–661 (2015). https://doi.org/10.1007/s11164-013-1218-9

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  • DOI: https://doi.org/10.1007/s11164-013-1218-9

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