An effective two-step synthesis, fluorescent properties, antioxidant activity and cytotoxicity evaluation of benzene-fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones

An effective two-step synthesis, fluorescent properties, antioxidant activity and cytotoxicity evaluation of benzene-fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2015, Volume: 178, Pages: 142-153 Pages count : DOI: 10.1016/j.jfluchem.2015.07.006

Tags

Sonogashira coupling; PTSA-catalyzed cyclocondensation; Benzene-fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones; Photophysical properties; Cytotoxicity against cancer cells; Mutagenic and antioxidant properties

Authors

Politanskaya Larisa V. ¹ , Chuikov Igor P. ¹ , Tretyakov Evgeny V. ¹ , Shteingarts Vitalij D. ¹ , Ovchinnikova Ludmila P. ² , Zakharova Olga D. ³ , Nevinsky Georgy A. ³

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, Inst Cytol & Genet, Siberian Div, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Inst Chem Biol & Fundamental Med, Siberian Div, Novosibirsk 630090, Russia

This study describes a simple and efficient procedure to synthesize a series of benzene-fluorinated 2,2dimethyl-2,3-dihydro-1H-quinolin-4-ones by the PTSA-catalyzed cyclocondensation reaction of the corresponding ortho-alkynylanilines prepared by the Sonogashira reaction of fluoro-substituted 2-iodanilines with 2-methylbut-3-yn-2-ol. The photofluorescent properties (shape of bands, lambda(ex), lambda(em), Stokes shift) of the new compounds were investigated. It has been revealed that the 2,3-dihydroquinolinones with different number of fluoro-substituents have almost the same fluorescence properties. The cytotoxicity evaluation of the 2,3-dihydroquinolinones against human myeloma, human mammary adenocarcinoma, human hepatocellular carcinoma HepG2 epithelial tumor cells, normal mouse fibroblasts and Chinese hamster Ag 17 cells was performed. It has been found that the benzoperfluorinated derivatives of 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones show enhanced cytotoxic effect against the tumor RPMI (human myeloma) cells line compared with the normal cells. Mutagenic and antioxidant properties of the compounds using Salmonella tester strain were studied. It has been shown, that the compounds are well antioxidants. (C) 2015 Elsevier B.V. All rights reserved.

Politanskaya L.V. , Chuikov I.P. , Tretyakov E.V. , Shteingarts V.D. , Ovchinnikova L.P. , Zakharova O.D. , Nevinsky G.A.
An effective two-step synthesis, fluorescent properties, antioxidant activity and cytotoxicity evaluation of benzene-fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones
Journal of Fluorine Chemistry. 2015. V.178. P.142-153. DOI: 10.1016/j.jfluchem.2015.07.006 WOS Scopus РИНЦ

Published print:

Oct 1, 2015

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