Čeština
EnglishSynthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1H)-quinolinones-7-carboxylic acids and their phenacyl esters
Soural, M.; Hlaváč, J.; Hradil, P.; Fryšová, I.; Hajdúch, M.; Bertolasi, V.; Maloň, Michal
JOURNAL OF MEDICINAL CHEMISTRY 41 [4]: 467-474, 2006
Keywords: Quinolinone; Cytotoxic activity; X-ray structure
Abstract: 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.
DOI:
IEB authors: bývalý zaměstnanec
JOURNAL OF MEDICINAL CHEMISTRY 41 [4]: 467-474, 2006
Keywords: Quinolinone; Cytotoxic activity; X-ray structure
Abstract: 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.
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