Biologically interesting polyfluorinated 2-aryl-2,3-dihydroquinolin-4-ones (5), 3-benzylidene-2-aryl-2,3-dihydroquinolin-4-ones (6) and 7-methyl-6-aryl-5,6-dihydrodibenzo[b,h][1,6] naphthyridines (7) were synthesized using a mild and efficient one-pot procedure starting from 2-aminoacetophenones and trifluorobenzaldehyde in the presence of p-toluenesulfonic acid. Thanks to the use of a high-active polyfluorinated electrophile this synthetic protocol provides rapid access to a variety of bioactive heterocyclic assemblies. Screening of the synthesized compounds for their cytotoxic activity against human tumor cell lines, including breast cancer (MCF-7), lung carcinoma (A-549), and myeloma cancer cells (RPMI 8226) revealed that polyfluorinated compounds 6b–f showed manifest cytotoxic effects (with IC50 = 2.5 ÷ 7 μM for MCF-7 and RPMI 8226 cancer cells).
- Cytotoxicity against cancer cells
- p-TSA-induced cyclocondensation
- Polyfluorinated quinolinones
- SOLVENT-FREE CONDITIONS
- AZA-MICHAEL ADDITION
- CORRESPONDING 2-ARYL-2,3-DIHYDROQUINOLIN-4(1H)-ONES
- HIGHLY EFFICIENT