Synthesis of 17α-substituted ethynylestradiols: Potential ligands for drug vectors
17α-substituted ethynylestradiols, derived from estrone, were converted to their corresponding 17α-(bromo- or iodo-propargyl)estrone intermediates. Nucleophilic substitution onto these moieties with malonate diester followed by hydrolysis and complexation with cis-Pt(Me 2en)I 2 (Me 2en = N, N-dimeth...
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| Veröffentlicht in: | Steroids 2010-07, Vol.75 (7), p.489-498 |
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| container_issue | 7 |
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| container_title | Steroids |
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| creator | Yaya, Amadou R. Touaibia, Mohamed Massarweh, Gassan Rochon, Fernande D. Breau, Livain |
| description | 17α-substituted ethynylestradiols, derived from estrone, were converted to their corresponding 17α-(bromo- or iodo-propargyl)estrone intermediates. Nucleophilic substitution onto these moieties with malonate diester followed by hydrolysis and complexation with
cis-Pt(Me
2en)I
2 (Me
2en
=
N,
N-dimethylethylenediamine) gave
cis-Pt(Me
2en)(2-(3-(17β-estradiol-17α-yl)-prop-2-ynyl)malonato)
7, thus demonstrating that these estrogen-derived compounds can be used to synthesize stable Pt(II) complexes. The 3-(17β-estradiol-17α
-yl)-prop-2-ynyl-1-sulfanylethylthiol
23 was also prepared. |
| doi_str_mv | 10.1016/j.steroids.2010.03.004 |
| format | Article |
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cis-Pt(Me
2en)I
2 (Me
2en
=
N,
N-dimethylethylenediamine) gave
cis-Pt(Me
2en)(2-(3-(17β-estradiol-17α-yl)-prop-2-ynyl)malonato)
7, thus demonstrating that these estrogen-derived compounds can be used to synthesize stable Pt(II) complexes. The 3-(17β-estradiol-17α
-yl)-prop-2-ynyl-1-sulfanylethylthiol
23 was also prepared.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/j.steroids.2010.03.004</identifier><identifier>PMID: 20302883</identifier><identifier>CODEN: STEDAM</identifier><language>eng</language><publisher>Kidlington: Elsevier Inc</publisher><subject>Anti-cancer ; Biological and medical sciences ; Drug Carriers ; Estradiol ; Estrone derivatives ; Ethinyl Estradiol - chemical synthesis ; Ethinyl Estradiol - chemistry ; Fundamental and applied biological sciences. Psychology ; Ligands ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Models, Chemical ; Molecular Structure ; Steroid–metal complexes ; Vertebrates: endocrinology</subject><ispartof>Steroids, 2010-07, Vol.75 (7), p.489-498</ispartof><rights>2010</rights><rights>2015 INIST-CNRS</rights><rights>(c) 2010. Published by Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c397t-811a6004403f25b3503293fa214414d82c85b7c67ed1b0d952149ad4645935843</citedby><cites>FETCH-LOGICAL-c397t-811a6004403f25b3503293fa214414d82c85b7c67ed1b0d952149ad4645935843</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.steroids.2010.03.004$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,45974</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22798664$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20302883$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yaya, Amadou R.</creatorcontrib><creatorcontrib>Touaibia, Mohamed</creatorcontrib><creatorcontrib>Massarweh, Gassan</creatorcontrib><creatorcontrib>Rochon, Fernande D.</creatorcontrib><creatorcontrib>Breau, Livain</creatorcontrib><title>Synthesis of 17α-substituted ethynylestradiols: Potential ligands for drug vectors</title><title>Steroids</title><addtitle>Steroids</addtitle><description>17α-substituted ethynylestradiols, derived from estrone, were converted to their corresponding 17α-(bromo- or iodo-propargyl)estrone intermediates. Nucleophilic substitution onto these moieties with malonate diester followed by hydrolysis and complexation with
cis-Pt(Me
2en)I
2 (Me
2en
=
N,
N-dimethylethylenediamine) gave
cis-Pt(Me
2en)(2-(3-(17β-estradiol-17α-yl)-prop-2-ynyl)malonato)
7, thus demonstrating that these estrogen-derived compounds can be used to synthesize stable Pt(II) complexes. The 3-(17β-estradiol-17α
-yl)-prop-2-ynyl-1-sulfanylethylthiol
23 was also prepared.</description><subject>Anti-cancer</subject><subject>Biological and medical sciences</subject><subject>Drug Carriers</subject><subject>Estradiol</subject><subject>Estrone derivatives</subject><subject>Ethinyl Estradiol - chemical synthesis</subject><subject>Ethinyl Estradiol - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Ligands</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Models, Chemical</subject><subject>Molecular Structure</subject><subject>Steroid–metal complexes</subject><subject>Vertebrates: endocrinology</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkF1rFDEUhoModq3-hTI34tWsJ8lMPrxSil9QsNAK3oVMkmmzzE5qTqawP6t_xN9klt3aS68O5DzvyctDyBmFNQUq3m_WWEJO0eOaQX0EvgbonpEVVVK1vRLyOVkBcN1Spn6dkFeIGwAQXLOX5IQBB6YUX5Grq91cbgNGbNLYUPnnocVlwBLLUoJvQrndzbspYMnWxzThh-YylTCXaKdmijd29tiMKTc-LzfNfXAlZXxNXox2wvDmOE_Jzy-fr8-_tRc_vn4__3TROq5laRWlVtTSHfCR9QPvgTPNR8to19HOK-ZUP0gnZPB0AK_7utDWd6LrNe9Vx0_Ju8Pdu5x-L7Wj2UZ0YZrsHNKCRnKuaU3JSooD6XJCzGE0dzlubd4ZCmbv02zMo0-z92mAm1qtBs-OXyzDNvh_sUeBFXh7BCw6O43Zzi7iE8ekVkLsD308cKEKuY8hG3QxzC74mKs141P8X5e_xfyXaw</recordid><startdate>20100701</startdate><enddate>20100701</enddate><creator>Yaya, Amadou R.</creator><creator>Touaibia, Mohamed</creator><creator>Massarweh, Gassan</creator><creator>Rochon, Fernande D.</creator><creator>Breau, Livain</creator><general>Elsevier Inc</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>20100701</creationdate><title>Synthesis of 17α-substituted ethynylestradiols: Potential ligands for drug vectors</title><author>Yaya, Amadou R. ; Touaibia, Mohamed ; Massarweh, Gassan ; Rochon, Fernande D. ; Breau, Livain</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c397t-811a6004403f25b3503293fa214414d82c85b7c67ed1b0d952149ad4645935843</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Anti-cancer</topic><topic>Biological and medical sciences</topic><topic>Drug Carriers</topic><topic>Estradiol</topic><topic>Estrone derivatives</topic><topic>Ethinyl Estradiol - chemical synthesis</topic><topic>Ethinyl Estradiol - chemistry</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Ligands</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Models, Chemical</topic><topic>Molecular Structure</topic><topic>Steroid–metal complexes</topic><topic>Vertebrates: endocrinology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yaya, Amadou R.</creatorcontrib><creatorcontrib>Touaibia, Mohamed</creatorcontrib><creatorcontrib>Massarweh, Gassan</creatorcontrib><creatorcontrib>Rochon, Fernande D.</creatorcontrib><creatorcontrib>Breau, Livain</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>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yaya, Amadou R.</au><au>Touaibia, Mohamed</au><au>Massarweh, Gassan</au><au>Rochon, Fernande D.</au><au>Breau, Livain</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 17α-substituted ethynylestradiols: Potential ligands for drug vectors</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>2010-07-01</date><risdate>2010</risdate><volume>75</volume><issue>7</issue><spage>489</spage><epage>498</epage><pages>489-498</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><coden>STEDAM</coden><abstract>17α-substituted ethynylestradiols, derived from estrone, were converted to their corresponding 17α-(bromo- or iodo-propargyl)estrone intermediates. Nucleophilic substitution onto these moieties with malonate diester followed by hydrolysis and complexation with
cis-Pt(Me
2en)I
2 (Me
2en
=
N,
N-dimethylethylenediamine) gave
cis-Pt(Me
2en)(2-(3-(17β-estradiol-17α-yl)-prop-2-ynyl)malonato)
7, thus demonstrating that these estrogen-derived compounds can be used to synthesize stable Pt(II) complexes. The 3-(17β-estradiol-17α
-yl)-prop-2-ynyl-1-sulfanylethylthiol
23 was also prepared.</abstract><cop>Kidlington</cop><pub>Elsevier Inc</pub><pmid>20302883</pmid><doi>10.1016/j.steroids.2010.03.004</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Steroids, 2010-07, Vol.75 (7), p.489-498 |
| issn | 0039-128X 1878-5867 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Anti-cancer Biological and medical sciences Drug Carriers Estradiol Estrone derivatives Ethinyl Estradiol - chemical synthesis Ethinyl Estradiol - chemistry Fundamental and applied biological sciences. Psychology Ligands Magnetic Resonance Spectroscopy Mass Spectrometry Models, Chemical Molecular Structure Steroid–metal complexes Vertebrates: endocrinology |
| title | Synthesis of 17α-substituted ethynylestradiols: Potential ligands for drug vectors |
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