p-Toluenesulfonic acid mediated one-pot cascade synthesis and cytotoxicity evaluation of polyfluorinated 2-aryl-2,3-dihydroquinolin-4-ones and their derivatives

Larisa Politanskaya, Tatyana Rybalova, Olga Zakharova, Georgy Nevinsky, Evgeny Tretyakov

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)129-140
Number of pages12
JournalJournal of Fluorine Chemistry
Volume211
DOIs
Publication statusPublished - 1 Jul 2018

Keywords

  • Cytotoxicity against cancer cells
  • p-TSA-induced cyclocondensation
  • Polyfluorinated quinolinones
  • ASYMMETRIC-SYNTHESIS
  • SOLVENT-FREE CONDITIONS
  • AZA-MICHAEL ADDITION
  • CORRESPONDING 2-ARYL-2,3-DIHYDROQUINOLIN-4(1H)-ONES
  • CATALYST
  • HIGHLY EFFICIENT
  • 2-ARYL-2,3-DIHYDRO-4-QUINOLONES
  • 2'-AMINOCHALCONES
  • 2-AMINOCHALCONES
  • CYCLIZATION

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