( R)-Goniothalamin: total syntheses and cytotoxic activity against cancer cell lines
The total syntheses of ( R)-goniothalamin ( 1) via catalytic asymmetric allylation of α-benzyloxyacetaldehyde ( 2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of trans-cinnamaldehyde followed by ring-closing metathesis are reported. The antipro...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2005-04, Vol.13 (8), p.2927-2933 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | de Fátima, Ângelo Kohn, Luciana Konecny Antônio, Márcia Aparecida de Carvalho, João Ernesto Pilli, Ronaldo Aloise |
| description | The total syntheses of (
R)-goniothalamin (
1) via catalytic asymmetric allylation of α-benzyloxyacetaldehyde (
2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of
trans-cinnamaldehyde followed by ring-closing metathesis are reported. The antiproliferative activities of (
R)-
1 and its
Z-isomer
10 as well as of the synthetic dihydropyranone intermediates
7 and
8 against eight different cancer cell lines are also described.
The total syntheses of (
R)-goniothalamin (
1), a styryl lactone isolated from several
Goniothalamus species, via catalytic asymmetric allylation of α-benzyloxyacetaldehyde (
2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of
trans-cinnamaldehyde (
12), followed by ring-closing metathesis are reported. The antiproliferative activities of (
R)-
1 and its
Z-isomer
10 as well as of the synthetic dihydropyranone intermediates
7 and
8 against eight different cancer cell lines are also described. |
| doi_str_mv | 10.1016/j.bmc.2005.02.007 |
| format | Article |
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R)-goniothalamin (
1) via catalytic asymmetric allylation of α-benzyloxyacetaldehyde (
2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of
trans-cinnamaldehyde followed by ring-closing metathesis are reported. The antiproliferative activities of (
R)-
1 and its
Z-isomer
10 as well as of the synthetic dihydropyranone intermediates
7 and
8 against eight different cancer cell lines are also described.
The total syntheses of (
R)-goniothalamin (
1), a styryl lactone isolated from several
Goniothalamus species, via catalytic asymmetric allylation of α-benzyloxyacetaldehyde (
2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of
trans-cinnamaldehyde (
12), followed by ring-closing metathesis are reported. The antiproliferative activities of (
R)-
1 and its
Z-isomer
10 as well as of the synthetic dihydropyranone intermediates
7 and
8 against eight different cancer cell lines are also described.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2005.02.007</identifier><identifier>PMID: 15781402</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>( R)-Goniothalamin ; Annonaceae - chemistry ; Antineoplastic agents ; Asymmetric synthesis ; Biological and medical sciences ; Cancer cells ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Cytotoxic activity ; Drug Screening Assays, Antitumor ; General aspects ; Humans ; Medical sciences ; Miscellaneous ; Molecular Conformation ; Pharmacology. Drug treatments ; Pyrones - chemical synthesis ; Pyrones - chemistry ; Pyrones - pharmacology ; Stereoisomerism</subject><ispartof>Bioorganic & medicinal chemistry, 2005-04, Vol.13 (8), p.2927-2933</ispartof><rights>2005 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c447t-993b911c81e8fe41d0e0eba784e809d21e335346f5d935fadf1123e72c3050f23</citedby><cites>FETCH-LOGICAL-c447t-993b911c81e8fe41d0e0eba784e809d21e335346f5d935fadf1123e72c3050f23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2005.02.007$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27928,27929,45999</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16661478$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15781402$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>de Fátima, Ângelo</creatorcontrib><creatorcontrib>Kohn, Luciana Konecny</creatorcontrib><creatorcontrib>Antônio, Márcia Aparecida</creatorcontrib><creatorcontrib>de Carvalho, João Ernesto</creatorcontrib><creatorcontrib>Pilli, Ronaldo Aloise</creatorcontrib><title>( R)-Goniothalamin: total syntheses and cytotoxic activity against cancer cell lines</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>The total syntheses of (
R)-goniothalamin (
1) via catalytic asymmetric allylation of α-benzyloxyacetaldehyde (
2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of
trans-cinnamaldehyde followed by ring-closing metathesis are reported. The antiproliferative activities of (
R)-
1 and its
Z-isomer
10 as well as of the synthetic dihydropyranone intermediates
7 and
8 against eight different cancer cell lines are also described.
The total syntheses of (
R)-goniothalamin (
1), a styryl lactone isolated from several
Goniothalamus species, via catalytic asymmetric allylation of α-benzyloxyacetaldehyde (
2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of
trans-cinnamaldehyde (
12), followed by ring-closing metathesis are reported. The antiproliferative activities of (
R)-
1 and its
Z-isomer
10 as well as of the synthetic dihydropyranone intermediates
7 and
8 against eight different cancer cell lines are also described.</description><subject>( R)-Goniothalamin</subject><subject>Annonaceae - chemistry</subject><subject>Antineoplastic agents</subject><subject>Asymmetric synthesis</subject><subject>Biological and medical sciences</subject><subject>Cancer cells</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Cytotoxic activity</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Miscellaneous</subject><subject>Molecular Conformation</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyrones - chemical synthesis</subject><subject>Pyrones - chemistry</subject><subject>Pyrones - pharmacology</subject><subject>Stereoisomerism</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kF1rFDEUhoModlv9Ad5IbpR6MeM5SSaTqVdStBUKhVKvQzZzxmaZj5pkS_ffm2UXeufVgcPzvrw8jH1AqBFQf93U68nXAqCpQdQA7Su2QqVVJWWHr9kKOm0qMJ0-YacpbQBAqA7fshNsWoMKxIrdn_O7L9XVMoclP7jRTWG-4HnJbuRpN-cHSpS4m3vud-W7PAfPnc_hKeQdd39cmFPm3s2eIvc0jnwMM6V37M3gxkTvj_eM_f754_7yurq5vfp1-f2m8kq1ueo6ue4QvUEyAynsgYDWrjWKDHS9QJKykUoPTd_JZnD9gCgktcJLaGAQ8ox9PvQ-xuXvllK2U0j7GW6mZZusbhthpJIFxAPo45JSpME-xjC5uLMIdq_SbmxRafcqLQhbVJbMx2P5dj1R_5I4uivApyPgknfjEIuGkF44rTWq1hTu24GjouIpULTJByrK-hDJZ9sv4T8z_gHoo5Bq</recordid><startdate>20050415</startdate><enddate>20050415</enddate><creator>de Fátima, Ângelo</creator><creator>Kohn, Luciana Konecny</creator><creator>Antônio, Márcia Aparecida</creator><creator>de Carvalho, João Ernesto</creator><creator>Pilli, Ronaldo Aloise</creator><general>Elsevier Ltd</general><general>Elsevier Science</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>20050415</creationdate><title>( R)-Goniothalamin: total syntheses and cytotoxic activity against cancer cell lines</title><author>de Fátima, Ângelo ; Kohn, Luciana Konecny ; Antônio, Márcia Aparecida ; de Carvalho, João Ernesto ; Pilli, Ronaldo Aloise</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c447t-993b911c81e8fe41d0e0eba784e809d21e335346f5d935fadf1123e72c3050f23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>( R)-Goniothalamin</topic><topic>Annonaceae - chemistry</topic><topic>Antineoplastic agents</topic><topic>Asymmetric synthesis</topic><topic>Biological and medical sciences</topic><topic>Cancer cells</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Cytotoxic activity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Miscellaneous</topic><topic>Molecular Conformation</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyrones - chemical synthesis</topic><topic>Pyrones - chemistry</topic><topic>Pyrones - pharmacology</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>de Fátima, Ângelo</creatorcontrib><creatorcontrib>Kohn, Luciana Konecny</creatorcontrib><creatorcontrib>Antônio, Márcia Aparecida</creatorcontrib><creatorcontrib>de Carvalho, João Ernesto</creatorcontrib><creatorcontrib>Pilli, Ronaldo Aloise</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>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>de Fátima, Ângelo</au><au>Kohn, Luciana Konecny</au><au>Antônio, Márcia Aparecida</au><au>de Carvalho, João Ernesto</au><au>Pilli, Ronaldo Aloise</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>( R)-Goniothalamin: total syntheses and cytotoxic activity against cancer cell lines</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2005-04-15</date><risdate>2005</risdate><volume>13</volume><issue>8</issue><spage>2927</spage><epage>2933</epage><pages>2927-2933</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>The total syntheses of (
R)-goniothalamin (
1) via catalytic asymmetric allylation of α-benzyloxyacetaldehyde (
2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of
trans-cinnamaldehyde followed by ring-closing metathesis are reported. The antiproliferative activities of (
R)-
1 and its
Z-isomer
10 as well as of the synthetic dihydropyranone intermediates
7 and
8 against eight different cancer cell lines are also described.
The total syntheses of (
R)-goniothalamin (
1), a styryl lactone isolated from several
Goniothalamus species, via catalytic asymmetric allylation of α-benzyloxyacetaldehyde (
2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of
trans-cinnamaldehyde (
12), followed by ring-closing metathesis are reported. The antiproliferative activities of (
R)-
1 and its
Z-isomer
10 as well as of the synthetic dihydropyranone intermediates
7 and
8 against eight different cancer cell lines are also described.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>15781402</pmid><doi>10.1016/j.bmc.2005.02.007</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2005-04, Vol.13 (8), p.2927-2933 |
| issn | 0968-0896 1464-3391 |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | ( R)-Goniothalamin Annonaceae - chemistry Antineoplastic agents Asymmetric synthesis Biological and medical sciences Cancer cells Cell Line, Tumor Cell Proliferation - drug effects Cytotoxic activity Drug Screening Assays, Antitumor General aspects Humans Medical sciences Miscellaneous Molecular Conformation Pharmacology. Drug treatments Pyrones - chemical synthesis Pyrones - chemistry Pyrones - pharmacology Stereoisomerism |
| title | ( R)-Goniothalamin: total syntheses and cytotoxic activity against cancer cell lines |
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