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

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

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2018, Volume: 211, Pages: 129-140 Pages count : 12 DOI: 10.1016/j.jfluchem.2018.04.005

Tags

p-TSA-induced cyclocondensation; Polyfluorinated quinolinones; Cytotoxicity against cancer cells

Authors

Politanskaya Larisa ^1,2 , Rybalova Tatyana ^1,2 , Zakharova Olga ³ , Nevinsky Georgy ^2,3 , Tretyakov Evgeny ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Inst Organ Chem, Ac Lavrentiev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova Str 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, Inst Chem Biol & Fundamental Med, Ac Lavrentiev Ave 8, Novosibirsk 630090, Russia

Biologically interesting polyfluorinated 2-aryl-2,3-dihydroquinolin-4-ones (5), 3-benzylidene-2-ary1-2,3-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 divided by 7 mu M for MCF-7 and RPMI 8226 cancer cells).

Politanskaya L. , Rybalova T. , Zakharova O. , Nevinsky G. , Tretyakov E.
p-Toluenesulfonic acid mediated one-pot cascade synthesis and cytotoxicity evaluation of polyfluorinated 2-aryl-2,3-dihydroquinolin-4-ones and their Check for updates derivatives
Journal of Fluorine Chemistry. 2018. V.211. P.129-140. DOI: 10.1016/j.jfluchem.2018.04.005 WOS Scopus РИНЦ

Published print:

Jul 1, 2018

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