Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1H)-quinolinones-7-carboxylic acids and their phenacyl esters.
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 alpha-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.
Soural
Miroslav
M
Department of Organic Chemistry, Faculty of Science, Palacký University, Olomouc, Czech Republic.
Hlavác
Jan
J
Hradil
Pavel
P
Frysová
Iveta
I
Hajdúch
Marián
M
Bertolasi
Valerio
V
Malon
Michal
M
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000494:pharmacology; D001682:Biological Availability; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D004952:Esters / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D011804:Quinolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013778:Tetrazolium Salts; D013844:Thiazoles
D000970:Antineoplastic Agents; D002264:Carboxylic Acids; D004952:Esters; D007202:Indicators and Reagents; D011804:Quinolines; D013778:Tetrazolium Salts; D013844:Thiazoles; C022616:thiazolyl blue