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

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p-Toluenesulfonic acid mediated one-pot cascade synthesis and cytotoxicity evaluation of polyfluorinated 2-aryl-2,3-dihydroquinolin-4-ones and their derivatives. / Politanskaya, Larisa; Rybalova, Tatyana; Zakharova, Olga et al.

In: Journal of Fluorine Chemistry, Vol. 211, 01.07.2018, p. 129-140.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{d40ce9c5411748aea1b4c1bf5dbeb40a,

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

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).",

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",

author = "Larisa Politanskaya and Tatyana Rybalova and Olga Zakharova and Georgy Nevinsky and Evgeny Tretyakov",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier B.V.",

year = "2018",

month = jul,

day = "1",

doi = "10.1016/j.jfluchem.2018.04.005",

language = "English",

volume = "211",

pages = "129--140",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - p-Toluenesulfonic acid mediated one-pot cascade synthesis and cytotoxicity evaluation of polyfluorinated 2-aryl-2,3-dihydroquinolin-4-ones and their derivatives

AU - Politanskaya, Larisa

AU - Rybalova, Tatyana

AU - Zakharova, Olga

AU - Nevinsky, Georgy

AU - Tretyakov, Evgeny

PY - 2018/7/1

Y1 - 2018/7/1

N2 - 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).

AB - 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).

KW - Cytotoxicity against cancer cells

KW - p-TSA-induced cyclocondensation

KW - Polyfluorinated quinolinones

KW - ASYMMETRIC-SYNTHESIS

KW - SOLVENT-FREE CONDITIONS

KW - AZA-MICHAEL ADDITION

KW - CORRESPONDING 2-ARYL-2,3-DIHYDROQUINOLIN-4(1H)-ONES

KW - CATALYST

KW - HIGHLY EFFICIENT

KW - 2-ARYL-2,3-DIHYDRO-4-QUINOLONES

KW - 2'-AMINOCHALCONES

KW - 2-AMINOCHALCONES

KW - CYCLIZATION

UR - http://www.scopus.com/inward/record.url?scp=85046775306&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2018.04.005

DO - 10.1016/j.jfluchem.2018.04.005

M3 - Article

AN - SCOPUS:85046775306

VL - 211

SP - 129

EP - 140

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

ER -

ID: 13355165