Abstract
Novel functionalized 2-amino-4-(4-oxo-4H-chromen-3-yl)-5-(2,2,2-trifluoroacetyl)-6-(trifluoro-methyl)-4H-pyrans and 2-amino-4-(4-oxo-4H-chromen-3-yl)-5-(thiophene-2-carbonyl)-6-(trifluoromethyl)-4H-pyrans have been synthesized by one-pot three-component reaction of 4-oxo-4H-chromene-3-carbaldehyde with three active methylene cyanoacetic acid derivatives and 1,1,1,5,5,5-hexafluoropentane-2,4-dione or 1,1,1-tri-fluoro-5-(thiophen-2-yl)pentane-2,4-dione in distilled water at 60-70 degrees C without a catalyst. The described methodology displayed excellent yields and simple workup procedure. The synthesized compounds were assessed for their in vitro anticancer activity against human breast cancer (MCF-7), liver cancer (HepG-2), and colon cancer cell lines (HCT-116). One of the compounds, 2-amino-4-(4-oxo-4H-chromen-3-yl)-5-(2,2,2-trifluoroacetyl)-6-(trifluoromethyl)-4H-pyran-3-carbonitrile, exhibited excellent anticancer activity versus all tested cancer cell lines with IC50 values ranging from 0.7 to 1.4 mu g/mL.