Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure
Synthesis of a set of schweinfurthin analogues varied in the D-ring alkyl substituent and stilbene moiety has been accomplished, and the activity of these compounds has been measured in a two-cell line screen. The most potent analogue and a much less active compound also were tested in the NCI 60-ce...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2010-02, Vol.18 (4), p.1676-1683 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Ulrich, Natalie C. Kodet, John G. Mente, Nolan R. Kuder, Craig H. Beutler, John A. Hohl, Raymond J. Wiemer, David F. |
| description | Synthesis of a set of schweinfurthin analogues varied in the D-ring alkyl substituent and stilbene moiety has been accomplished, and the activity of these compounds has been measured in a two-cell line screen. The most potent analogue and a much less active compound also were tested in the NCI 60-cell line assay, and showed comparable potency in that more extensive screen.
The natural tetracyclic schweinfurthins are potent and selective inhibitors of cell growth in the National Cancer Institute’s 60-cell line screen. An interest in determination of their cellular or molecular target has inspired our efforts to prepare both the natural products and analogues. In this paper, chemical synthesis of analogues modified in different olefinic positions, and preliminary results from studies of their biological activity, are reported. |
| doi_str_mv | 10.1016/j.bmc.2009.12.063 |
| format | Article |
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The natural tetracyclic schweinfurthins are potent and selective inhibitors of cell growth in the National Cancer Institute’s 60-cell line screen. An interest in determination of their cellular or molecular target has inspired our efforts to prepare both the natural products and analogues. In this paper, chemical synthesis of analogues modified in different olefinic positions, and preliminary results from studies of their biological activity, are reported.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2009.12.063</identifier><identifier>PMID: 20116262</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Anti-proliferative ; Antineoplastic agents ; Bioassay ; Biological and medical sciences ; Cell Division - drug effects ; Cell Line, Tumor ; Drug Screening Assays, Antitumor ; General aspects ; Humans ; Magnetic Resonance Spectroscopy ; Medical sciences ; Molecular Probes ; Molecular Structure ; Pharmacology. Drug treatments ; Schweinfurthin ; Spectrometry, Mass, Electrospray Ionization ; Stilbene ; Stilbenes - chemistry ; Synthesis</subject><ispartof>Bioorganic & medicinal chemistry, 2010-02, Vol.18 (4), p.1676-1683</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c480t-87db6bbf66b3c7e92032d70094b41fa7bb8c53d4f089cf6e3562b7f3d874e5bd3</citedby><cites>FETCH-LOGICAL-c480t-87db6bbf66b3c7e92032d70094b41fa7bb8c53d4f089cf6e3562b7f3d874e5bd3</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.2009.12.063$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22830602$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20116262$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ulrich, Natalie C.</creatorcontrib><creatorcontrib>Kodet, John G.</creatorcontrib><creatorcontrib>Mente, Nolan R.</creatorcontrib><creatorcontrib>Kuder, Craig H.</creatorcontrib><creatorcontrib>Beutler, John A.</creatorcontrib><creatorcontrib>Hohl, Raymond J.</creatorcontrib><creatorcontrib>Wiemer, David F.</creatorcontrib><title>Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Synthesis of a set of schweinfurthin analogues varied in the D-ring alkyl substituent and stilbene moiety has been accomplished, and the activity of these compounds has been measured in a two-cell line screen. The most potent analogue and a much less active compound also were tested in the NCI 60-cell line assay, and showed comparable potency in that more extensive screen.
The natural tetracyclic schweinfurthins are potent and selective inhibitors of cell growth in the National Cancer Institute’s 60-cell line screen. An interest in determination of their cellular or molecular target has inspired our efforts to prepare both the natural products and analogues. In this paper, chemical synthesis of analogues modified in different olefinic positions, and preliminary results from studies of their biological activity, are reported.</description><subject>Anti-proliferative</subject><subject>Antineoplastic agents</subject><subject>Bioassay</subject><subject>Biological and medical sciences</subject><subject>Cell Division - drug effects</subject><subject>Cell Line, Tumor</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>Humans</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Molecular Probes</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Schweinfurthin</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Stilbene</subject><subject>Stilbenes - chemistry</subject><subject>Synthesis</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUtv1DAUhS0EotPCD2CDvGFHgh-Jk4CEhEoLSJVAAtaWH9cTjzLOyHaKuuKv42iGAhtWvpK_c-7jIPSMkpoSKl7tar03NSNkqCmrieAP0IY2oqk4H-hDtCGD6CvSD-IMnae0I4SwZqCP0RkjlAom2Ab9_JrjYvIS1YRVUNO8XSDh2eFkxh_gg1tiHn3A16_xlzhrH7Y4j4BThujNSwwTmBznsNYqWDze2TgfxgIafCgVxOyPfqvqfRVXg7TodOoKT9Ajp6YET0_vBfp-ffXt8mN18_nDp8t3N5VpepKrvrNaaO2E0Nx0MDDCme3K4o1uqFOd1r1puW1c2dY4AbwVTHeO275roNWWX6C3R9_DovdgDYRcVpaH6Pcq3slZefnvT_Cj3M63sm0ZEWwoBvRoYOKcUgR3r6VErmnInSxpyDUNSZksaRTN87-b3it-n78AL06ASkZNLqpgfPrDsZ4TQVbuzZGDcqJbD1Em4yEYsD6WAKSd_X_G-AVya6vn</recordid><startdate>20100215</startdate><enddate>20100215</enddate><creator>Ulrich, Natalie C.</creator><creator>Kodet, John G.</creator><creator>Mente, Nolan R.</creator><creator>Kuder, Craig H.</creator><creator>Beutler, John A.</creator><creator>Hohl, Raymond J.</creator><creator>Wiemer, David F.</creator><general>Elsevier Ltd</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>5PM</scope></search><sort><creationdate>20100215</creationdate><title>Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure</title><author>Ulrich, Natalie C. ; Kodet, John G. ; Mente, Nolan R. ; Kuder, Craig H. ; Beutler, John A. ; Hohl, Raymond J. ; Wiemer, David F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c480t-87db6bbf66b3c7e92032d70094b41fa7bb8c53d4f089cf6e3562b7f3d874e5bd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Anti-proliferative</topic><topic>Antineoplastic agents</topic><topic>Bioassay</topic><topic>Biological and medical sciences</topic><topic>Cell Division - drug effects</topic><topic>Cell Line, Tumor</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>Humans</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Molecular Probes</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Schweinfurthin</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Stilbene</topic><topic>Stilbenes - chemistry</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ulrich, Natalie C.</creatorcontrib><creatorcontrib>Kodet, John G.</creatorcontrib><creatorcontrib>Mente, Nolan R.</creatorcontrib><creatorcontrib>Kuder, Craig H.</creatorcontrib><creatorcontrib>Beutler, John A.</creatorcontrib><creatorcontrib>Hohl, Raymond J.</creatorcontrib><creatorcontrib>Wiemer, David F.</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>PubMed Central (Full Participant titles)</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ulrich, Natalie C.</au><au>Kodet, John G.</au><au>Mente, Nolan R.</au><au>Kuder, Craig H.</au><au>Beutler, John A.</au><au>Hohl, Raymond J.</au><au>Wiemer, David F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2010-02-15</date><risdate>2010</risdate><volume>18</volume><issue>4</issue><spage>1676</spage><epage>1683</epage><pages>1676-1683</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Synthesis of a set of schweinfurthin analogues varied in the D-ring alkyl substituent and stilbene moiety has been accomplished, and the activity of these compounds has been measured in a two-cell line screen. The most potent analogue and a much less active compound also were tested in the NCI 60-cell line assay, and showed comparable potency in that more extensive screen.
The natural tetracyclic schweinfurthins are potent and selective inhibitors of cell growth in the National Cancer Institute’s 60-cell line screen. An interest in determination of their cellular or molecular target has inspired our efforts to prepare both the natural products and analogues. In this paper, chemical synthesis of analogues modified in different olefinic positions, and preliminary results from studies of their biological activity, are reported.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20116262</pmid><doi>10.1016/j.bmc.2009.12.063</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2010-02, Vol.18 (4), p.1676-1683 |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Anti-proliferative Antineoplastic agents Bioassay Biological and medical sciences Cell Division - drug effects Cell Line, Tumor Drug Screening Assays, Antitumor General aspects Humans Magnetic Resonance Spectroscopy Medical sciences Molecular Probes Molecular Structure Pharmacology. Drug treatments Schweinfurthin Spectrometry, Mass, Electrospray Ionization Stilbene Stilbenes - chemistry Synthesis |
| title | Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure |
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