Isocombretastatins A versus Combretastatins A: The Forgotten isoCA-4 Isomer as a Highly Promising Cytotoxic and Antitubulin Agent
Herein is reported a convergent synthesis of isocombretastatins A, a novel class of potent antitubulin agents. These compounds having a 1,1-diarylethylene scaffold constitute the simplest isomers of natural Z-combretastatins A that are easy to synthesize without need to control the Z-olefin geometry...
Gespeichert in:
| Veröffentlicht in: | Journal of medicinal chemistry 2009-07, Vol.52 (14), p.4538-4542 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 4542 |
|---|---|
| container_issue | 14 |
| container_start_page | 4538 |
| container_title | Journal of medicinal chemistry |
| container_volume | 52 |
| creator | Messaoudi, Samir Tréguier, Bret Hamze, Abdallah Provot, Olivier Peyrat, Jean-François De Losada, Jordi Rodrigo Liu, Jian-Miao Bignon, Jérôme Wdzieczak-Bakala, Joanna Thoret, Sylviane Dubois, Joëlle Brion, Jean-Daniel Alami, Mouâd |
| description | Herein is reported a convergent synthesis of isocombretastatins A, a novel class of potent antitubulin agents. These compounds having a 1,1-diarylethylene scaffold constitute the simplest isomers of natural Z-combretastatins A that are easy to synthesize without need to control the Z-olefin geometry. The discovery of isoCA-4 with biological activities comparable to that of CA-4 represents a major progress in this field. |
| doi_str_mv | 10.1021/jm900321u |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_00421101v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67494253</sourcerecordid><originalsourceid>FETCH-LOGICAL-a369t-2995d6cfaf6849f875f753e6c46b41ca57e0cf68034f4e5d6928a11abfc97873</originalsourceid><addsrcrecordid>eNpd0U1rGzEQBmBRUhon7aF_oOiSQg7b6ms_1NuyNHHA0B58F7Oy1pbZlVJJG-Jj_nkU4jqQ08DMwwszg9BXSn5QwujP_SQJ4YzOH9CClowUoiHiDC0IYaxgFePn6CLGPcmIMv4JnVNZclLJZoGe7qLXfuqDSRATJOsibvGDCXGOuHs_-IXXO4NvfNj6lIzDNvquLQTOIZMJGCIGvLTb3XjAf4OfbLRui7tD8sk_Wo3BbXDrkk1zP4_W4XZrXPqMPg4wRvPlWC_R-ub3ulsWqz-3d127KoBXMhVMynJT6QGGqhFyaOpyqEtuKi2qXlANZW2IzjPCxSBMppI1QCn0g5Z1U_NLdP0au4NR3Qc7QTgoD1Yt25V66REiGKWEPtBsv7_a--D_zSYmlVfRZhzBGT9HVdVCClbyDL8d4dxPZnPK_X_fDK6OAKKGcQjgtI0nxxiRrKzFmwMd1d7PweVTKErUy3_V6b_8GXp8lKE</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67494253</pqid></control><display><type>article</type><title>Isocombretastatins A versus Combretastatins A: The Forgotten isoCA-4 Isomer as a Highly Promising Cytotoxic and Antitubulin Agent</title><source>MEDLINE</source><source>ACS Publications</source><creator>Messaoudi, Samir ; Tréguier, Bret ; Hamze, Abdallah ; Provot, Olivier ; Peyrat, Jean-François ; De Losada, Jordi Rodrigo ; Liu, Jian-Miao ; Bignon, Jérôme ; Wdzieczak-Bakala, Joanna ; Thoret, Sylviane ; Dubois, Joëlle ; Brion, Jean-Daniel ; Alami, Mouâd</creator><creatorcontrib>Messaoudi, Samir ; Tréguier, Bret ; Hamze, Abdallah ; Provot, Olivier ; Peyrat, Jean-François ; De Losada, Jordi Rodrigo ; Liu, Jian-Miao ; Bignon, Jérôme ; Wdzieczak-Bakala, Joanna ; Thoret, Sylviane ; Dubois, Joëlle ; Brion, Jean-Daniel ; Alami, Mouâd</creatorcontrib><description>Herein is reported a convergent synthesis of isocombretastatins A, a novel class of potent antitubulin agents. These compounds having a 1,1-diarylethylene scaffold constitute the simplest isomers of natural Z-combretastatins A that are easy to synthesize without need to control the Z-olefin geometry. The discovery of isoCA-4 with biological activities comparable to that of CA-4 represents a major progress in this field.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm900321u</identifier><identifier>PMID: 19530698</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Columbus, OH: American Chemical Society</publisher><subject>Antineoplastic Agents ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Bibenzyls ; Bibenzyls - chemistry ; Bibenzyls - pharmacology ; Biological and medical sciences ; Cell Line, Tumor ; Cell Proliferation ; Cell Proliferation - drug effects ; Cellular Biology ; Chlorophenols ; Chlorophenols - chemistry ; Chlorophenols - pharmacology ; General aspects ; Humans ; Life Sciences ; Medical sciences ; Models, Molecular ; Molecular Conformation ; Peptides, Cyclic ; Peptides, Cyclic - chemistry ; Peptides, Cyclic - pharmacology ; Pharmacology. Drug treatments ; Stereoisomerism ; Tubulin Modulators ; Tubulin Modulators - chemistry ; Tubulin Modulators - pharmacology</subject><ispartof>Journal of medicinal chemistry, 2009-07, Vol.52 (14), p.4538-4542</ispartof><rights>Copyright © 2009 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0003-4601-462X ; 0000-0002-6294-9671 ; 0000-0002-4994-9001</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm900321u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm900321u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,315,782,786,887,27085,27933,27934,56747,56797</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22092574$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19530698$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00421101$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Messaoudi, Samir</creatorcontrib><creatorcontrib>Tréguier, Bret</creatorcontrib><creatorcontrib>Hamze, Abdallah</creatorcontrib><creatorcontrib>Provot, Olivier</creatorcontrib><creatorcontrib>Peyrat, Jean-François</creatorcontrib><creatorcontrib>De Losada, Jordi Rodrigo</creatorcontrib><creatorcontrib>Liu, Jian-Miao</creatorcontrib><creatorcontrib>Bignon, Jérôme</creatorcontrib><creatorcontrib>Wdzieczak-Bakala, Joanna</creatorcontrib><creatorcontrib>Thoret, Sylviane</creatorcontrib><creatorcontrib>Dubois, Joëlle</creatorcontrib><creatorcontrib>Brion, Jean-Daniel</creatorcontrib><creatorcontrib>Alami, Mouâd</creatorcontrib><title>Isocombretastatins A versus Combretastatins A: The Forgotten isoCA-4 Isomer as a Highly Promising Cytotoxic and Antitubulin Agent</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Herein is reported a convergent synthesis of isocombretastatins A, a novel class of potent antitubulin agents. These compounds having a 1,1-diarylethylene scaffold constitute the simplest isomers of natural Z-combretastatins A that are easy to synthesize without need to control the Z-olefin geometry. The discovery of isoCA-4 with biological activities comparable to that of CA-4 represents a major progress in this field.</description><subject>Antineoplastic Agents</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Bibenzyls</subject><subject>Bibenzyls - chemistry</subject><subject>Bibenzyls - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation</subject><subject>Cell Proliferation - drug effects</subject><subject>Cellular Biology</subject><subject>Chlorophenols</subject><subject>Chlorophenols - chemistry</subject><subject>Chlorophenols - pharmacology</subject><subject>General aspects</subject><subject>Humans</subject><subject>Life Sciences</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Peptides, Cyclic</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptides, Cyclic - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Stereoisomerism</subject><subject>Tubulin Modulators</subject><subject>Tubulin Modulators - chemistry</subject><subject>Tubulin Modulators - pharmacology</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0U1rGzEQBmBRUhon7aF_oOiSQg7b6ms_1NuyNHHA0B58F7Oy1pbZlVJJG-Jj_nkU4jqQ08DMwwszg9BXSn5QwujP_SQJ4YzOH9CClowUoiHiDC0IYaxgFePn6CLGPcmIMv4JnVNZclLJZoGe7qLXfuqDSRATJOsibvGDCXGOuHs_-IXXO4NvfNj6lIzDNvquLQTOIZMJGCIGvLTb3XjAf4OfbLRui7tD8sk_Wo3BbXDrkk1zP4_W4XZrXPqMPg4wRvPlWC_R-ub3ulsWqz-3d127KoBXMhVMynJT6QGGqhFyaOpyqEtuKi2qXlANZW2IzjPCxSBMppI1QCn0g5Z1U_NLdP0au4NR3Qc7QTgoD1Yt25V66REiGKWEPtBsv7_a--D_zSYmlVfRZhzBGT9HVdVCClbyDL8d4dxPZnPK_X_fDK6OAKKGcQjgtI0nxxiRrKzFmwMd1d7PweVTKErUy3_V6b_8GXp8lKE</recordid><startdate>20090723</startdate><enddate>20090723</enddate><creator>Messaoudi, Samir</creator><creator>Tréguier, Bret</creator><creator>Hamze, Abdallah</creator><creator>Provot, Olivier</creator><creator>Peyrat, Jean-François</creator><creator>De Losada, Jordi Rodrigo</creator><creator>Liu, Jian-Miao</creator><creator>Bignon, Jérôme</creator><creator>Wdzieczak-Bakala, Joanna</creator><creator>Thoret, Sylviane</creator><creator>Dubois, Joëlle</creator><creator>Brion, Jean-Daniel</creator><creator>Alami, Mouâd</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-4601-462X</orcidid><orcidid>https://orcid.org/0000-0002-6294-9671</orcidid><orcidid>https://orcid.org/0000-0002-4994-9001</orcidid></search><sort><creationdate>20090723</creationdate><title>Isocombretastatins A versus Combretastatins A: The Forgotten isoCA-4 Isomer as a Highly Promising Cytotoxic and Antitubulin Agent</title><author>Messaoudi, Samir ; Tréguier, Bret ; Hamze, Abdallah ; Provot, Olivier ; Peyrat, Jean-François ; De Losada, Jordi Rodrigo ; Liu, Jian-Miao ; Bignon, Jérôme ; Wdzieczak-Bakala, Joanna ; Thoret, Sylviane ; Dubois, Joëlle ; Brion, Jean-Daniel ; Alami, Mouâd</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a369t-2995d6cfaf6849f875f753e6c46b41ca57e0cf68034f4e5d6928a11abfc97873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Antineoplastic Agents</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Bibenzyls</topic><topic>Bibenzyls - chemistry</topic><topic>Bibenzyls - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation</topic><topic>Cell Proliferation - drug effects</topic><topic>Cellular Biology</topic><topic>Chlorophenols</topic><topic>Chlorophenols - chemistry</topic><topic>Chlorophenols - pharmacology</topic><topic>General aspects</topic><topic>Humans</topic><topic>Life Sciences</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Peptides, Cyclic</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Peptides, Cyclic - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Stereoisomerism</topic><topic>Tubulin Modulators</topic><topic>Tubulin Modulators - chemistry</topic><topic>Tubulin Modulators - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Messaoudi, Samir</creatorcontrib><creatorcontrib>Tréguier, Bret</creatorcontrib><creatorcontrib>Hamze, Abdallah</creatorcontrib><creatorcontrib>Provot, Olivier</creatorcontrib><creatorcontrib>Peyrat, Jean-François</creatorcontrib><creatorcontrib>De Losada, Jordi Rodrigo</creatorcontrib><creatorcontrib>Liu, Jian-Miao</creatorcontrib><creatorcontrib>Bignon, Jérôme</creatorcontrib><creatorcontrib>Wdzieczak-Bakala, Joanna</creatorcontrib><creatorcontrib>Thoret, Sylviane</creatorcontrib><creatorcontrib>Dubois, Joëlle</creatorcontrib><creatorcontrib>Brion, Jean-Daniel</creatorcontrib><creatorcontrib>Alami, Mouâd</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>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Messaoudi, Samir</au><au>Tréguier, Bret</au><au>Hamze, Abdallah</au><au>Provot, Olivier</au><au>Peyrat, Jean-François</au><au>De Losada, Jordi Rodrigo</au><au>Liu, Jian-Miao</au><au>Bignon, Jérôme</au><au>Wdzieczak-Bakala, Joanna</au><au>Thoret, Sylviane</au><au>Dubois, Joëlle</au><au>Brion, Jean-Daniel</au><au>Alami, Mouâd</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isocombretastatins A versus Combretastatins A: The Forgotten isoCA-4 Isomer as a Highly Promising Cytotoxic and Antitubulin Agent</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2009-07-23</date><risdate>2009</risdate><volume>52</volume><issue>14</issue><spage>4538</spage><epage>4542</epage><pages>4538-4542</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Herein is reported a convergent synthesis of isocombretastatins A, a novel class of potent antitubulin agents. These compounds having a 1,1-diarylethylene scaffold constitute the simplest isomers of natural Z-combretastatins A that are easy to synthesize without need to control the Z-olefin geometry. The discovery of isoCA-4 with biological activities comparable to that of CA-4 represents a major progress in this field.</abstract><cop>Columbus, OH</cop><pub>American Chemical Society</pub><pmid>19530698</pmid><doi>10.1021/jm900321u</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-4601-462X</orcidid><orcidid>https://orcid.org/0000-0002-6294-9671</orcidid><orcidid>https://orcid.org/0000-0002-4994-9001</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 2009-07, Vol.52 (14), p.4538-4542 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_00421101v1 |
| source | MEDLINE; ACS Publications |
| subjects | Antineoplastic Agents Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Bibenzyls Bibenzyls - chemistry Bibenzyls - pharmacology Biological and medical sciences Cell Line, Tumor Cell Proliferation Cell Proliferation - drug effects Cellular Biology Chlorophenols Chlorophenols - chemistry Chlorophenols - pharmacology General aspects Humans Life Sciences Medical sciences Models, Molecular Molecular Conformation Peptides, Cyclic Peptides, Cyclic - chemistry Peptides, Cyclic - pharmacology Pharmacology. Drug treatments Stereoisomerism Tubulin Modulators Tubulin Modulators - chemistry Tubulin Modulators - pharmacology |
| title | Isocombretastatins A versus Combretastatins A: The Forgotten isoCA-4 Isomer as a Highly Promising Cytotoxic and Antitubulin Agent |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-02T21%3A38%3A08IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Isocombretastatins%20A%20versus%20Combretastatins%20A:%20The%20Forgotten%20isoCA-4%20Isomer%20as%20a%20Highly%20Promising%20Cytotoxic%20and%20Antitubulin%20Agent&rft.jtitle=Journal%20of%20medicinal%20chemistry&rft.au=Messaoudi,%20Samir&rft.date=2009-07-23&rft.volume=52&rft.issue=14&rft.spage=4538&rft.epage=4542&rft.pages=4538-4542&rft.issn=0022-2623&rft.eissn=1520-4804&rft.coden=JMCMAR&rft_id=info:doi/10.1021/jm900321u&rft_dat=%3Cproquest_hal_p%3E67494253%3C/proquest_hal_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=67494253&rft_id=info:pmid/19530698&rfr_iscdi=true |