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Viridin analogs derived from steroidal building blocks
Naturally occurring furanosteroids such as viridin and wortmannin have long been known as potent inhibitors of the lipid kinase PI-3K. We have been interested in directly accessing analogs of these complex natural products from abundant steroid feedstock materials. In this communication, we describe...
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| Published in: | Bioorganic & medicinal chemistry letters 2012-11, Vol.22 (22), p.6919-6922 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c410t-fe56a4a45faf3a5242027332aff41fb699116c76c6349cae75f1b7bc87a70b563 |
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| cites | cdi_FETCH-LOGICAL-c410t-fe56a4a45faf3a5242027332aff41fb699116c76c6349cae75f1b7bc87a70b563 |
| container_end_page | 6922 |
| container_issue | 22 |
| container_start_page | 6919 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 22 |
| creator | Viswanathan, Kishore Ononye, Sophia N. Cooper, Harold D. Kyle Hadden, M. Anderson, Amy C. Wright, Dennis L. |
| description | Naturally occurring furanosteroids such as viridin and wortmannin have long been known as potent inhibitors of the lipid kinase PI-3K. We have been interested in directly accessing analogs of these complex natural products from abundant steroid feedstock materials. In this communication, we describe the synthesis of viridin/wortmannin hybrid molecules from readily available building blocks that function as PI-3K inhibitors and maintain their electrophilic properties. The compounds also show anti-proliferative effects against a breast cancer line. |
| doi_str_mv | 10.1016/j.bmcl.2012.09.015 |
| format | article |
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We have been interested in directly accessing analogs of these complex natural products from abundant steroid feedstock materials. In this communication, we describe the synthesis of viridin/wortmannin hybrid molecules from readily available building blocks that function as PI-3K inhibitors and maintain their electrophilic properties. The compounds also show anti-proliferative effects against a breast cancer line.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2012.09.015</identifier><identifier>PMID: 23040731</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Androstadienes - chemistry ; Androstenes - chemical synthesis ; Androstenes - chemistry ; Androstenes - toxicity ; Bacteriocins - chemical synthesis ; Bacteriocins - chemistry ; Bacteriocins - toxicity ; Binding Sites ; Biological and medical sciences ; breast neoplasms ; Breast Neoplasms - metabolism ; Breast Neoplasms - pathology ; Cell Survival - drug effects ; chemistry ; Crystallography, X-Ray ; electrophysiology ; enzyme inhibitors ; feedstocks ; Female ; Humans ; Irreversible enzyme inhibitors ; MCF-7 Cells ; Medical sciences ; Pharmacology. Drug treatments ; Phosphatidylinositol 3-Kinases - antagonists & inhibitors ; Phosphatidylinositol 3-Kinases - metabolism ; PI-3K ; Protein Kinase Inhibitors - chemical synthesis ; Protein Kinase Inhibitors - chemistry ; Protein Kinase Inhibitors - toxicity ; Protein Structure, Tertiary ; Steroid ; steroids ; Steroids - chemistry ; Viridin ; Wortmannin</subject><ispartof>Bioorganic & medicinal chemistry letters, 2012-11, Vol.22 (22), p.6919-6922</ispartof><rights>2012 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c410t-fe56a4a45faf3a5242027332aff41fb699116c76c6349cae75f1b7bc87a70b563</citedby><cites>FETCH-LOGICAL-c410t-fe56a4a45faf3a5242027332aff41fb699116c76c6349cae75f1b7bc87a70b563</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,783,787,27936,27937</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26593081$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23040731$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Viswanathan, Kishore</creatorcontrib><creatorcontrib>Ononye, Sophia N.</creatorcontrib><creatorcontrib>Cooper, Harold D.</creatorcontrib><creatorcontrib>Kyle Hadden, M.</creatorcontrib><creatorcontrib>Anderson, Amy C.</creatorcontrib><creatorcontrib>Wright, Dennis L.</creatorcontrib><title>Viridin analogs derived from steroidal building blocks</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Naturally occurring furanosteroids such as viridin and wortmannin have long been known as potent inhibitors of the lipid kinase PI-3K. We have been interested in directly accessing analogs of these complex natural products from abundant steroid feedstock materials. In this communication, we describe the synthesis of viridin/wortmannin hybrid molecules from readily available building blocks that function as PI-3K inhibitors and maintain their electrophilic properties. The compounds also show anti-proliferative effects against a breast cancer line.</description><subject>Androstadienes - chemistry</subject><subject>Androstenes - chemical synthesis</subject><subject>Androstenes - chemistry</subject><subject>Androstenes - toxicity</subject><subject>Bacteriocins - chemical synthesis</subject><subject>Bacteriocins - chemistry</subject><subject>Bacteriocins - toxicity</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>breast neoplasms</subject><subject>Breast Neoplasms - metabolism</subject><subject>Breast Neoplasms - pathology</subject><subject>Cell Survival - drug effects</subject><subject>chemistry</subject><subject>Crystallography, X-Ray</subject><subject>electrophysiology</subject><subject>enzyme inhibitors</subject><subject>feedstocks</subject><subject>Female</subject><subject>Humans</subject><subject>Irreversible enzyme inhibitors</subject><subject>MCF-7 Cells</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Phosphatidylinositol 3-Kinases - antagonists & inhibitors</subject><subject>Phosphatidylinositol 3-Kinases - metabolism</subject><subject>PI-3K</subject><subject>Protein Kinase Inhibitors - chemical synthesis</subject><subject>Protein Kinase Inhibitors - chemistry</subject><subject>Protein Kinase Inhibitors - toxicity</subject><subject>Protein Structure, Tertiary</subject><subject>Steroid</subject><subject>steroids</subject><subject>Steroids - chemistry</subject><subject>Viridin</subject><subject>Wortmannin</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp90LtqHDEUgGEREuKNnRdIEU9jSDPjo-usII0xzgUMLnwhnTijkRZtNCNb2jX47a1lN0mXSs13jqSfkE8UOgpUna-7YbKxY0BZB7oDKt-QBRVKtFyAfEsWoBW0Sy1-HZEPpawBqAAh3pMjxkFAz-mCqIeQwxjmBmeMaVWa0eXw7MbG5zQ1ZeNyCiPGZtiGWNmqGWKyv8sJeecxFvfxcB6T-29Xd5c_2uub7z8vL65bKyhsWu-kQoFCevQcJRMMWM85Q-8F9YPSmlJle2UVF9qi66WnQz_YZY89DFLxY_Jlv_cxp6etKxszhWJdjDi7tC2G0vpf3dcalbI9tTmVkp03jzlMmF8MBbPrZdZm18vsehnQpvaqQ58P-7fD5Ma_I38CVXB2AFgsRp9xtqH8c0pqDsudO907j8ngKldzf1tvkjU6p0yLKr7uhau9noPLptjgZuvGkJ3dmDGF_730Fe-bkM4</recordid><startdate>20121115</startdate><enddate>20121115</enddate><creator>Viswanathan, Kishore</creator><creator>Ononye, Sophia N.</creator><creator>Cooper, Harold D.</creator><creator>Kyle Hadden, M.</creator><creator>Anderson, Amy C.</creator><creator>Wright, Dennis L.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><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>20121115</creationdate><title>Viridin analogs derived from steroidal building blocks</title><author>Viswanathan, Kishore ; Ononye, Sophia N. ; Cooper, Harold D. ; Kyle Hadden, M. ; Anderson, Amy C. ; Wright, Dennis L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c410t-fe56a4a45faf3a5242027332aff41fb699116c76c6349cae75f1b7bc87a70b563</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Androstadienes - chemistry</topic><topic>Androstenes - chemical synthesis</topic><topic>Androstenes - chemistry</topic><topic>Androstenes - toxicity</topic><topic>Bacteriocins - chemical synthesis</topic><topic>Bacteriocins - chemistry</topic><topic>Bacteriocins - toxicity</topic><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>breast neoplasms</topic><topic>Breast Neoplasms - metabolism</topic><topic>Breast Neoplasms - pathology</topic><topic>Cell Survival - drug effects</topic><topic>chemistry</topic><topic>Crystallography, X-Ray</topic><topic>electrophysiology</topic><topic>enzyme inhibitors</topic><topic>feedstocks</topic><topic>Female</topic><topic>Humans</topic><topic>Irreversible enzyme inhibitors</topic><topic>MCF-7 Cells</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Phosphatidylinositol 3-Kinases - antagonists & inhibitors</topic><topic>Phosphatidylinositol 3-Kinases - metabolism</topic><topic>PI-3K</topic><topic>Protein Kinase Inhibitors - chemical synthesis</topic><topic>Protein Kinase Inhibitors - chemistry</topic><topic>Protein Kinase Inhibitors - toxicity</topic><topic>Protein Structure, Tertiary</topic><topic>Steroid</topic><topic>steroids</topic><topic>Steroids - chemistry</topic><topic>Viridin</topic><topic>Wortmannin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Viswanathan, Kishore</creatorcontrib><creatorcontrib>Ononye, Sophia N.</creatorcontrib><creatorcontrib>Cooper, Harold D.</creatorcontrib><creatorcontrib>Kyle Hadden, M.</creatorcontrib><creatorcontrib>Anderson, Amy C.</creatorcontrib><creatorcontrib>Wright, Dennis L.</creatorcontrib><collection>AGRIS</collection><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 letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Viswanathan, Kishore</au><au>Ononye, Sophia N.</au><au>Cooper, Harold D.</au><au>Kyle Hadden, M.</au><au>Anderson, Amy C.</au><au>Wright, Dennis L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Viridin analogs derived from steroidal building blocks</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2012-11-15</date><risdate>2012</risdate><volume>22</volume><issue>22</issue><spage>6919</spage><epage>6922</epage><pages>6919-6922</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Naturally occurring furanosteroids such as viridin and wortmannin have long been known as potent inhibitors of the lipid kinase PI-3K. We have been interested in directly accessing analogs of these complex natural products from abundant steroid feedstock materials. In this communication, we describe the synthesis of viridin/wortmannin hybrid molecules from readily available building blocks that function as PI-3K inhibitors and maintain their electrophilic properties. The compounds also show anti-proliferative effects against a breast cancer line.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>23040731</pmid><doi>10.1016/j.bmcl.2012.09.015</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2012-11, Vol.22 (22), p.6919-6922 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | ScienceDirect Freedom Collection |
| subjects | Androstadienes - chemistry Androstenes - chemical synthesis Androstenes - chemistry Androstenes - toxicity Bacteriocins - chemical synthesis Bacteriocins - chemistry Bacteriocins - toxicity Binding Sites Biological and medical sciences breast neoplasms Breast Neoplasms - metabolism Breast Neoplasms - pathology Cell Survival - drug effects chemistry Crystallography, X-Ray electrophysiology enzyme inhibitors feedstocks Female Humans Irreversible enzyme inhibitors MCF-7 Cells Medical sciences Pharmacology. Drug treatments Phosphatidylinositol 3-Kinases - antagonists & inhibitors Phosphatidylinositol 3-Kinases - metabolism PI-3K Protein Kinase Inhibitors - chemical synthesis Protein Kinase Inhibitors - chemistry Protein Kinase Inhibitors - toxicity Protein Structure, Tertiary Steroid steroids Steroids - chemistry Viridin Wortmannin |
| title | Viridin analogs derived from steroidal building blocks |
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