Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1H)-quinolinones-7-carboxylic acids and their phenacyl esters
Language English Country France Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
16540209
DOI
10.1016/j.ejmech.2005.12.008
PII: S0223-5234(06)00024-9
Knihovny.cz E-resources
- MeSH
- Biological Availability MeSH
- Quinolines chemical synthesis pharmacology MeSH
- Esters chemical synthesis pharmacology MeSH
- Indicators and Reagents MeSH
- Crystallography, X-Ray MeSH
- Carboxylic Acids chemical synthesis pharmacology MeSH
- Humans MeSH
- Magnetic Resonance Spectroscopy MeSH
- Models, Molecular MeSH
- Cell Line, Tumor MeSH
- Antineoplastic Agents chemical synthesis pharmacokinetics pharmacology MeSH
- Drug Screening Assays, Antitumor MeSH
- Tetrazolium Salts MeSH
- Thiazoles MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Quinolines MeSH
- Esters MeSH
- Indicators and Reagents MeSH
- Carboxylic Acids MeSH
- Antineoplastic Agents MeSH
- Tetrazolium Salts MeSH
- Thiazoles MeSH
- thiazolyl blue MeSH Browser
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.
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