Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1H)-quinolinones-7-carboxylic acids and their phenacyl esters

0083355 - ÚEB 2007 RIV FR eng J - Journal Article
Soural, M. - Hlaváč, J. - Hradil, P. - Fryšová, I. - Hajdúch, M. - Bertolasi, V. - Maloň, Michal
Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1H)-quinolinones-7-carboxylic acids and their phenacyl esters.
[Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1H)-quinolinones-7-carboxylic acids and their phenacyl esters.]
European Journal of Medicinal Chemistry. Roč. 41, č. 4 (2006), s. 467-474. ISSN 0223-5234. E-ISSN 1768-3254
Institutional research plan: CEZ:AV0Z50380511
Keywords : Quinolinone * Cytotoxic activity * X-ray structure
Subject RIV: CE - Biochemistry
Impact factor: 2.187, year: 2006

The preparation of 3-hydroxy-2-phenyl-4(1H)-quinolinones substituted in position 7 with a carboxyl group is described. The synthesis is based on the reaction of 2-aminoterephthalic acid with substituted α-bromoacetophenones and subsequent cyclization of the resulting bisphenacylesters in polyphosphoric acid. The reaction affords a mixture of substituted 3-hydroxy-2-phenyl-4(1H)-quinolinones 7-carboxylic acids as well as their phenacylesters. All quinolinones prepared (acids and phenacylesters) were tested for cytotoxic activity in vitro against five cancer cell lines and the results and a tentative structure–activity relationship are reported.

Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1H)-quinolinones-7-carboxylic acids and their phenacyl esters.
Permanent Link: http://hdl.handle.net/11104/0146620