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

• Published in: Journal of fluorine chemistry Vol. 178; pp. 142 - 153
• Main Authors: Politanskaya, Larisa V., Chuikov, Igor P., Tretyakov, Evgeny V., Shteingarts, Vitalij D., Ovchinnikova, Ludmila P., Zakharova, Olga D., Nevinsky, Georgy A.
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.10.2015; Elsevier
• Subjects: Benzene-fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Cytotoxicity against cancer cells; Mutagenic and antioxidant properties; Photophysical properties; Physical Sciences; PTSA-catalyzed cyclocondensation; Science & Technology; Sonogashira coupling; Sonogashira coupling; Cytotoxicity against cancer cells; Mutagenic and antioxidant properties; PTSA-catalyzed cyclocondensation; Benzene-fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones; Photophysical properties; PHOTOCHEMICAL PROPERTIES; AGENTS
• DOI: 10.1016/j.jfluchem.2015.07.006
• ISSN: 0022-1139

An efficient and practical procedure for the synthesis of benzene-fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones was developed and their photophysical, mutagenic, antioxidant properties and cytotoxicity activity against cancer cells were explored. •Synthesis of 8 fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones.•Perfluorinated derivatives showed enhanced cytotoxic effect against cancer cells.•Compounds suppress spontaneous and H2O2-induced mutagenesis of bacterial cells.•Fluorescence properties of fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones. This study describes a simple and efficient procedure to synthesize a series of benzene-fluorinated 2,2-dimethyl-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, λex, λem, 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 benzo-perfluorinated 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.