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Department of Organic ChemistryFaculty of SciencePalacký University Olomouc Laboratory of Experimental MedicineDepartments of Pediatrics and OncologyFaculty of Medicine Palacký University and Faculty Hospital in Olomouc Institutt for FarmasiUniversitetet i TromsoeTromsoe Norway |
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Minireviews in Medicinal Chemistry 2009, 9, 696-702.
2-Phenyl-3-hydroxy-4(1H)-quinolinones can be considered as aza-analogues of flavones,
compounds which are known for the wide-range of their biological activity. These
quinolinones were studied as inhibitors of topoisomerase, gyrase and IMPDH. They were
tested for anticancer activity in-vitro and were also shown to possess immunosuppressive
properties.
This review is the first summarizing the synthesis and activity of the mentioned
quinolinones.
European Journal of Organic Chemistry 2009, 3867–3870.
The preparation of novel organic disulfides containing the 2-(substituted phenyl)quinolin-4(1H)-one ring is described. The synthesis starts from thioanthranilic acid esterified with
various bromoacetophenones. Cyclization of the resulting phenacyl thioanthranilates in trifluoroacetic acid afforded a mixture of 2-(substituted phenyl)-3-sulfanylquinolin-4(1H)-
ones and 3,3_-disulfanediylbis[2-(substituted phenyl)quinolin-4(1H)-ones]. Heating of the mixture in o-xylene gave 3,3_- disulfanediylbis[2-(substituted phenyl)quinolin-4(1H)-ones]
of high purity. The disulfides exhibited a significant in vitro cytotoxicity against various cancer cell lines including polyresistant subclones. The data obtained are reported and discussed.
Journal of Combinatorial Chemistry 2009, 11, 951-955.
The efficient solid-phase synthesis of 3-hydroxy-2,7-disubstituted-6-nitroquinolin-4(1H)-ones using Rink amide resin is described. Synthesis starts from immobilized 4-chloro-5-nitroanthranilic acid which, after the nucleophilic replacement of the chlorine atom with various amines and subsequent esterification with bromoacetophenones, afforded substituted phenacylanthranilates. Their cyclization by heating in sulfuric acid gave corresponding hydroxyquinolinones of excellent purity.