Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1 H)-quinolinones-7-carboxylic acids and their phenacyl esters
The preparation of 3-hydroxy-2-phenyl-4(1 H)-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 polyphosph...
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| Veröffentlicht in: | European journal of medicinal chemistry 2006-04, Vol.41 (4), p.467-474 |
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| container_title | European journal of medicinal chemistry |
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| creator | Soural, Miroslav Hlaváč, Jan Hradil, Pavel Fryšová, Iveta Hajdúch, Marián Bertolasi, Valerio Maloň, Michal |
| description | The preparation of 3-hydroxy-2-phenyl-4(1
H)-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(1
H)-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_str_mv | 10.1016/j.ejmech.2005.12.008 |
| format | Article |
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H)-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(1
H)-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.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2005.12.008</identifier><identifier>PMID: 16540209</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacokinetics ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Biological Availability ; Carboxylic Acids - chemical synthesis ; Carboxylic Acids - pharmacology ; Cell Line, Tumor ; Crystallography, X-Ray ; Cytotoxic activity ; Drug Screening Assays, Antitumor ; Esters - chemical synthesis ; Esters - pharmacology ; General aspects ; Humans ; Indicators and Reagents ; Magnetic Resonance Spectroscopy ; Medical sciences ; Models, Molecular ; Pharmacology. Drug treatments ; Quinolines - chemical synthesis ; Quinolines - pharmacology ; Quinolinone ; Structure-Activity Relationship ; Tetrazolium Salts ; Thiazoles ; X-ray structure</subject><ispartof>European journal of medicinal chemistry, 2006-04, Vol.41 (4), p.467-474</ispartof><rights>2006 Elsevier SAS</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-7e61408db37d0259a3212c1276e4f2d447a4f7dd964c15489a20236231d4436b3</citedby><cites>FETCH-LOGICAL-c390t-7e61408db37d0259a3212c1276e4f2d447a4f7dd964c15489a20236231d4436b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2005.12.008$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17775612$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16540209$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Soural, Miroslav</creatorcontrib><creatorcontrib>Hlaváč, Jan</creatorcontrib><creatorcontrib>Hradil, Pavel</creatorcontrib><creatorcontrib>Fryšová, Iveta</creatorcontrib><creatorcontrib>Hajdúch, Marián</creatorcontrib><creatorcontrib>Bertolasi, Valerio</creatorcontrib><creatorcontrib>Maloň, Michal</creatorcontrib><title>Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1 H)-quinolinones-7-carboxylic acids and their phenacyl esters</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>The preparation of 3-hydroxy-2-phenyl-4(1
H)-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(1
H)-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.</description><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacokinetics</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Biological Availability</subject><subject>Carboxylic Acids - chemical synthesis</subject><subject>Carboxylic Acids - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Crystallography, X-Ray</subject><subject>Cytotoxic activity</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Esters - chemical synthesis</subject><subject>Esters - pharmacology</subject><subject>General aspects</subject><subject>Humans</subject><subject>Indicators and Reagents</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinolines - chemical synthesis</subject><subject>Quinolines - pharmacology</subject><subject>Quinolinone</subject><subject>Structure-Activity Relationship</subject><subject>Tetrazolium Salts</subject><subject>Thiazoles</subject><subject>X-ray structure</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc9u1DAQxi0EokvhDRDKBVQODv4Xe3NBQlWhSJU4AGfLsSdar7Lx1naq5gl4jX2WfTK8bKTeOIzmML_5vtF8CL2lpKaEyk_bGrY7sJuaEdLUlNWErJ-hFVVyjTlrxHO0Ioxx3DAuLtCrlLakgJKQl-iCykYQRtoV-vNzHvMGkk-VGd3xYOcccnj0tjI2-wef5yr0x0OaupR9njK4iuH9BsZ5wBxvZhfD44zFFa1uP-L7yY9hKDVCwgpbE7syHf6Jebc4FDcfj4eThrHzUEHKENNr9KI3Q4I3S79Ev7_e_Lq-xXc_vn2__nKHLW9JxgokFWTtOq4cYU1rOKPMUqYkiJ45IZQRvXKulcLSRqxbwwjjknFaZlx2_BJ9OOvuY7ifirfe-WRhGMwIYUpaqpYpwkUBxRm0MaQUodf76HcmzpoSfQpAb_U5AH0KQFOmSwBl7d2iP3U7cE9Ly8cL8H4BTLJm6KMZrU9PnFKqkZQV7vOZg_KNBw9RJ-thtOB8BJu1C_7_l_wFydGpiA</recordid><startdate>20060401</startdate><enddate>20060401</enddate><creator>Soural, Miroslav</creator><creator>Hlaváč, Jan</creator><creator>Hradil, Pavel</creator><creator>Fryšová, Iveta</creator><creator>Hajdúch, Marián</creator><creator>Bertolasi, Valerio</creator><creator>Maloň, Michal</creator><general>Elsevier Masson SAS</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20060401</creationdate><title>Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1 H)-quinolinones-7-carboxylic acids and their phenacyl esters</title><author>Soural, Miroslav ; Hlaváč, Jan ; Hradil, Pavel ; Fryšová, Iveta ; Hajdúch, Marián ; Bertolasi, Valerio ; Maloň, Michal</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-7e61408db37d0259a3212c1276e4f2d447a4f7dd964c15489a20236231d4436b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacokinetics</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Biological Availability</topic><topic>Carboxylic Acids - chemical synthesis</topic><topic>Carboxylic Acids - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Crystallography, X-Ray</topic><topic>Cytotoxic activity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Esters - chemical synthesis</topic><topic>Esters - pharmacology</topic><topic>General aspects</topic><topic>Humans</topic><topic>Indicators and Reagents</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinolines - chemical synthesis</topic><topic>Quinolines - pharmacology</topic><topic>Quinolinone</topic><topic>Structure-Activity Relationship</topic><topic>Tetrazolium Salts</topic><topic>Thiazoles</topic><topic>X-ray structure</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Soural, Miroslav</creatorcontrib><creatorcontrib>Hlaváč, Jan</creatorcontrib><creatorcontrib>Hradil, Pavel</creatorcontrib><creatorcontrib>Fryšová, Iveta</creatorcontrib><creatorcontrib>Hajdúch, Marián</creatorcontrib><creatorcontrib>Bertolasi, Valerio</creatorcontrib><creatorcontrib>Maloň, Michal</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Soural, Miroslav</au><au>Hlaváč, Jan</au><au>Hradil, Pavel</au><au>Fryšová, Iveta</au><au>Hajdúch, Marián</au><au>Bertolasi, Valerio</au><au>Maloň, Michal</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1 H)-quinolinones-7-carboxylic acids and their phenacyl esters</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2006-04-01</date><risdate>2006</risdate><volume>41</volume><issue>4</issue><spage>467</spage><epage>474</epage><pages>467-474</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>The preparation of 3-hydroxy-2-phenyl-4(1
H)-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(1
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| subjects | Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacokinetics Antineoplastic Agents - pharmacology Biological and medical sciences Biological Availability Carboxylic Acids - chemical synthesis Carboxylic Acids - pharmacology Cell Line, Tumor Crystallography, X-Ray Cytotoxic activity Drug Screening Assays, Antitumor Esters - chemical synthesis Esters - pharmacology General aspects Humans Indicators and Reagents Magnetic Resonance Spectroscopy Medical sciences Models, Molecular Pharmacology. Drug treatments Quinolines - chemical synthesis Quinolines - pharmacology Quinolinone Structure-Activity Relationship Tetrazolium Salts Thiazoles X-ray structure |
| title | Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1 H)-quinolinones-7-carboxylic acids and their phenacyl esters |
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