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Synthesis of some quinolinyl chalcone analogues and investigation of their anticancer and synergistic anticancer effect with doxorubicin

Two derivatives of 2-(4-acetylanilino)quinolines (IIIa, b) were synthesized as scaffolds for synthesis of open chalcone analogues (Va-f) through Claisen-Schmidt condensation with a set of aromatic aldehydes (IVa-d). Derivatives (Va, b) were further manipulated into cyclic α,β-unsaturated ketones by Michael-addition of acetylacetone and ethylacetoacetate affording derivatives (VI–VII). Deethoxycarboxylation of derivatives (VIIa, b) afforded cyclohexenons (VIIIa, b) allowing formation of a mini library of α,β-unsaturated ketones for screening their anticancer and synergistic anticancer effect with doxorubicin using colon cancer cell line (Caco-2). Two open enones, (Vb) and (Ve), showed significant anticancer activity with IC50 of 5.0 and 2.5 μM respectively. Only one cyclic enone, (VIa) showed synergistic anticancer activity with doxorubicin at 10 μM.

Authors:   Mohamed R. E. Aly, El-Sayed I. Ibrahim, Fakher A. El Shahed, Hamdy A. Soliman, Zein S. Ibrahim, Samir A. M. El-Shazly
Journal:   Russian Journal of Bioorganic Chemistry
Year:   2012
DOI:   10.1134/S1068162012030119
Publication date:   13-07-2012

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  • colon cancer
  • Claisen-Schmidt Condens…
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