A comparative structural study of the steroid epimers: 17β-amino-1,3,5(10)- estratrien-3-ol, 17α-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis
The epimers 17β-amino-1,3,5(10)-estratrien-3-ol and 17α-amino-1,3,5(10)-estratrien-3-ol were synthesized. 17β-Amino-1,3,5(10)-estratrien-3-ol was prepared by catalytic hydrogenation of the estrone–oxime. The 17α-amino epimer was obtained from estradiol, via tosylate, followed by nucleophilic displac...
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| Veröffentlicht in: | Steroids 1998-11, Vol.63 (11), p.556-564 |
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| creator | Lemini, Cristina Cruz–Ramos, Elia Toscano, Rubén Alfredo Cruz–Almanza, Raymundo |
| description | The epimers 17β-amino-1,3,5(10)-estratrien-3-ol and 17α-amino-1,3,5(10)-estratrien-3-ol were synthesized. 17β-Amino-1,3,5(10)-estratrien-3-ol was prepared by catalytic hydrogenation of the estrone–oxime. The 17α-amino epimer was obtained from estradiol, via tosylate, followed by nucleophilic displacement by sodium azide and subsequent reduction with LiAlH
4. They were characterized by spectroscopic methods. Determination of the crystal structures of 3-(toluene-4-sulfonyloxy)-17α-azido-1,3,5(10)-estratriene, 3-(toluene-4-sulfonyloxy)-17-α-amino-1,3,5(10)-estratriene hydrochloride, 17β-acetylamino-1,3,5(10)-estratriene-3-ol, and 3-acetoxy-17β-acetylamino-1,3,5(10)-estratriene enabled us to characterize the structure of the 17α and 17β amino epimers for the first time. |
| doi_str_mv | 10.1016/S0039-128X(98)00063-4 |
| format | Article |
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4. They were characterized by spectroscopic methods. Determination of the crystal structures of 3-(toluene-4-sulfonyloxy)-17α-azido-1,3,5(10)-estratriene, 3-(toluene-4-sulfonyloxy)-17-α-amino-1,3,5(10)-estratriene hydrochloride, 17β-acetylamino-1,3,5(10)-estratriene-3-ol, and 3-acetoxy-17β-acetylamino-1,3,5(10)-estratriene enabled us to characterize the structure of the 17α and 17β amino epimers for the first time.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/S0039-128X(98)00063-4</identifier><identifier>PMID: 9830681</identifier><identifier>CODEN: STEDAM</identifier><language>eng</language><publisher>New York, NY: Elsevier Inc</publisher><subject>17-aminosteroids ; 17α-aminoestrogens ; 17β-aminoestrogens ; 1H NMR ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds ; Chemistry ; Condensed matter: structure, mechanical and thermal properties ; Crystallography, X-Ray ; epimers ; Estradiol Congeners - chemistry ; Exact sciences and technology ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Molecular Structure ; Organic chemistry ; Organic compounds ; Physics ; Preparations and properties ; Steroids ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids ; X-ray</subject><ispartof>Steroids, 1998-11, Vol.63 (11), p.556-564</ispartof><rights>1998 Elsevier Science Inc.</rights><rights>1999 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2361-4d37beceecda4d2a63dca9cc223509db8467efcb31b5e9a45adcaa3811c574d23</citedby><cites>FETCH-LOGICAL-c2361-4d37beceecda4d2a63dca9cc223509db8467efcb31b5e9a45adcaa3811c574d23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0039-128X(98)00063-4$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1630979$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9830681$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lemini, Cristina</creatorcontrib><creatorcontrib>Cruz–Ramos, Elia</creatorcontrib><creatorcontrib>Toscano, Rubén Alfredo</creatorcontrib><creatorcontrib>Cruz–Almanza, Raymundo</creatorcontrib><title>A comparative structural study of the steroid epimers: 17β-amino-1,3,5(10)- estratrien-3-ol, 17α-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis</title><title>Steroids</title><addtitle>Steroids</addtitle><description>The epimers 17β-amino-1,3,5(10)-estratrien-3-ol and 17α-amino-1,3,5(10)-estratrien-3-ol were synthesized. 17β-Amino-1,3,5(10)-estratrien-3-ol was prepared by catalytic hydrogenation of the estrone–oxime. The 17α-amino epimer was obtained from estradiol, via tosylate, followed by nucleophilic displacement by sodium azide and subsequent reduction with LiAlH
4. They were characterized by spectroscopic methods. Determination of the crystal structures of 3-(toluene-4-sulfonyloxy)-17α-azido-1,3,5(10)-estratriene, 3-(toluene-4-sulfonyloxy)-17-α-amino-1,3,5(10)-estratriene hydrochloride, 17β-acetylamino-1,3,5(10)-estratriene-3-ol, and 3-acetoxy-17β-acetylamino-1,3,5(10)-estratriene enabled us to characterize the structure of the 17α and 17β amino epimers for the first time.</description><subject>17-aminosteroids</subject><subject>17α-aminoestrogens</subject><subject>17β-aminoestrogens</subject><subject>1H NMR</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</subject><subject>Chemistry</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Crystallography, X-Ray</subject><subject>epimers</subject><subject>Estradiol Congeners - chemistry</subject><subject>Exact sciences and technology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Organic compounds</subject><subject>Physics</subject><subject>Preparations and properties</subject><subject>Steroids</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><subject>X-ray</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkdtqFTEUhoModVt9hEIuRFrY0WQyh8QbKaVaoSp4AO_CmmQNRmYm22Rm434s-wg-gM9k9oF60QuvEtb_rZWV_yfkRPDngov6xSfOpWaiUF9PtTrjnNeSlffIQqhGsUrVzX2yuEUekkcpfd9BujgiR1pJXiuxIL_PqQ3DCiJMfo00TXG20xyhz9fZbWjo6PRtW8cYvKO48gPG9JKK5s8Ng8GPgYmlXFangp8xirkfpuhxZJKFfrnFft3B7lAwOprCgNRh9OvdJom2Gyqu6Pt3H_f6TxZhQ53vugh28mHMVeg3yafH5EEHfcInh_OYfHl9-fniil1_ePP24vya2ULWgpVONi1aROugdAXU0lnQ1haFrLh2rSrrBjvbStFWqKGsIOsglRC2anKDPCbP9nNXMfyY8yfM4JPFvocRw5xMk91VWtUZrPagjSGliJ1ZRT9A3BjBzTY7s8vObIMxWpldLKbMfSeHB-Z2QHfbdQgr608POiQLfTZitD79G15LrhudsVd7DLMZa4_RJJu9tuh8RDsZF_x_FvkLcE22-g</recordid><startdate>199811</startdate><enddate>199811</enddate><creator>Lemini, Cristina</creator><creator>Cruz–Ramos, Elia</creator><creator>Toscano, Rubén Alfredo</creator><creator>Cruz–Almanza, Raymundo</creator><general>Elsevier Inc</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>199811</creationdate><title>A comparative structural study of the steroid epimers: 17β-amino-1,3,5(10)- estratrien-3-ol, 17α-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis</title><author>Lemini, Cristina ; Cruz–Ramos, Elia ; Toscano, Rubén Alfredo ; Cruz–Almanza, Raymundo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2361-4d37beceecda4d2a63dca9cc223509db8467efcb31b5e9a45adcaa3811c574d23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>17-aminosteroids</topic><topic>17α-aminoestrogens</topic><topic>17β-aminoestrogens</topic><topic>1H NMR</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</topic><topic>Chemistry</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Crystallography, X-Ray</topic><topic>epimers</topic><topic>Estradiol Congeners - chemistry</topic><topic>Exact sciences and technology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Organic compounds</topic><topic>Physics</topic><topic>Preparations and properties</topic><topic>Steroids</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><topic>X-ray</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lemini, Cristina</creatorcontrib><creatorcontrib>Cruz–Ramos, Elia</creatorcontrib><creatorcontrib>Toscano, Rubén Alfredo</creatorcontrib><creatorcontrib>Cruz–Almanza, Raymundo</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>Lemini, Cristina</au><au>Cruz–Ramos, Elia</au><au>Toscano, Rubén Alfredo</au><au>Cruz–Almanza, Raymundo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A comparative structural study of the steroid epimers: 17β-amino-1,3,5(10)- estratrien-3-ol, 17α-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>1998-11</date><risdate>1998</risdate><volume>63</volume><issue>11</issue><spage>556</spage><epage>564</epage><pages>556-564</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><coden>STEDAM</coden><abstract>The epimers 17β-amino-1,3,5(10)-estratrien-3-ol and 17α-amino-1,3,5(10)-estratrien-3-ol were synthesized. 17β-Amino-1,3,5(10)-estratrien-3-ol was prepared by catalytic hydrogenation of the estrone–oxime. The 17α-amino epimer was obtained from estradiol, via tosylate, followed by nucleophilic displacement by sodium azide and subsequent reduction with LiAlH
4. They were characterized by spectroscopic methods. Determination of the crystal structures of 3-(toluene-4-sulfonyloxy)-17α-azido-1,3,5(10)-estratriene, 3-(toluene-4-sulfonyloxy)-17-α-amino-1,3,5(10)-estratriene hydrochloride, 17β-acetylamino-1,3,5(10)-estratriene-3-ol, and 3-acetoxy-17β-acetylamino-1,3,5(10)-estratriene enabled us to characterize the structure of the 17α and 17β amino epimers for the first time.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>9830681</pmid><doi>10.1016/S0039-128X(98)00063-4</doi><tpages>9</tpages></addata></record> |
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| ispartof | Steroids, 1998-11, Vol.63 (11), p.556-564 |
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| language | eng |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | 17-aminosteroids 17α-aminoestrogens 17β-aminoestrogens 1H NMR Alicyclic compounds, terpenoids, prostaglandins, steroids Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds Chemistry Condensed matter: structure, mechanical and thermal properties Crystallography, X-Ray epimers Estradiol Congeners - chemistry Exact sciences and technology Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Structure Organic chemistry Organic compounds Physics Preparations and properties Steroids Structure of solids and liquids crystallography Structure of specific crystalline solids X-ray |
| title | A comparative structural study of the steroid epimers: 17β-amino-1,3,5(10)- estratrien-3-ol, 17α-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis |
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