Stereochemical studies of 3-aryl-3-methylpiperidines of potential opioid ligand activities by high-resolution 1H and 13C NMR spectroscopy
The 1H (270, 400 MHz) and 13C (22.5, 67.5 MHz) NMR spectra of a series of 2,3‐3,5‐ and 3,6‐dimethyl‐3‐(m‐hydroxy‐m‐methoxy‐phenyl)piperidines of proven or potential opioid ligand activity are reported. The data were analysed in terms of configuration and preferred conformation, and some key deductio...
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| Veröffentlicht in: | Magnetic resonance in chemistry 1987-06, Vol.25 (6), p.524-530 |
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| container_title | Magnetic resonance in chemistry |
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| creator | Casy, A. F. Iorio, M. A. Madani, A. E. |
| description | The 1H (270, 400 MHz) and 13C (22.5, 67.5 MHz) NMR spectra of a series of 2,3‐3,5‐ and 3,6‐dimethyl‐3‐(m‐hydroxy‐m‐methoxy‐phenyl)piperidines of proven or potential opioid ligand activity are reported. The data were analysed in terms of configuration and preferred conformation, and some key deductions were confirmed by NOED and 2D COSY experiments. In the 3,5‐dimethyl derivatives, isomers with preferred axial or equatorial 3‐aryl substituents were identified. |
| doi_str_mv | 10.1002/mrc.1260250614 |
| format | Article |
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F. ; Iorio, M. A. ; Madani, A. E.</creator><creatorcontrib>Casy, A. F. ; Iorio, M. A. ; Madani, A. E.</creatorcontrib><description>The 1H (270, 400 MHz) and 13C (22.5, 67.5 MHz) NMR spectra of a series of 2,3‐3,5‐ and 3,6‐dimethyl‐3‐(m‐hydroxy‐m‐methoxy‐phenyl)piperidines of proven or potential opioid ligand activity are reported. The data were analysed in terms of configuration and preferred conformation, and some key deductions were confirmed by NOED and 2D COSY experiments. In the 3,5‐dimethyl derivatives, isomers with preferred axial or equatorial 3‐aryl substituents were identified.</description><identifier>ISSN: 0749-1581</identifier><identifier>EISSN: 1097-458X</identifier><identifier>DOI: 10.1002/mrc.1260250614</identifier><identifier>CODEN: MRCHEG</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>13C NMR ; 1H NMR ; 3-Aryl-3-methylpiperidines ; Atomic and molecular physics ; Barrier heights (internal rotation, inversion, rotational isomerism, conformational dynamics) ; conformational analysis ; Exact sciences and technology ; Molecular properties and interactions with photons ; Physics ; Properties of molecules and molecular ions ; stereochemistry</subject><ispartof>Magnetic resonance in chemistry, 1987-06, Vol.25 (6), p.524-530</ispartof><rights>Copyright © 1987 John Wiley & Sons Ltd.</rights><rights>1988 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fmrc.1260250614$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fmrc.1260250614$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7487944$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Casy, A. F.</creatorcontrib><creatorcontrib>Iorio, M. A.</creatorcontrib><creatorcontrib>Madani, A. E.</creatorcontrib><title>Stereochemical studies of 3-aryl-3-methylpiperidines of potential opioid ligand activities by high-resolution 1H and 13C NMR spectroscopy</title><title>Magnetic resonance in chemistry</title><addtitle>Magn. Reson. Chem</addtitle><description>The 1H (270, 400 MHz) and 13C (22.5, 67.5 MHz) NMR spectra of a series of 2,3‐3,5‐ and 3,6‐dimethyl‐3‐(m‐hydroxy‐m‐methoxy‐phenyl)piperidines of proven or potential opioid ligand activity are reported. The data were analysed in terms of configuration and preferred conformation, and some key deductions were confirmed by NOED and 2D COSY experiments. In the 3,5‐dimethyl derivatives, isomers with preferred axial or equatorial 3‐aryl substituents were identified.</description><subject>13C NMR</subject><subject>1H NMR</subject><subject>3-Aryl-3-methylpiperidines</subject><subject>Atomic and molecular physics</subject><subject>Barrier heights (internal rotation, inversion, rotational isomerism, conformational dynamics)</subject><subject>conformational analysis</subject><subject>Exact sciences and technology</subject><subject>Molecular properties and interactions with photons</subject><subject>Physics</subject><subject>Properties of molecules and molecular ions</subject><subject>stereochemistry</subject><issn>0749-1581</issn><issn>1097-458X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><recordid>eNpFkEFv1DAUhC1EJZaWK2cfuLr42U4cH9EKWtDuIrVFIC6W4zjdB9k4sl0gP4F_TVaL2tPT08w30gwhr4FfAufi7SH5SxA1FxWvQT0jK-BGM1U1356TFdfKMKgaeEFe5vyDc26Mlivy97aEFKLfhwN6N9BcHjoMmcaeSubSPDDJDqHs52HCKSTscDypUyxhLLggccKIHR3w3o0ddb7gLyzHjHame7zfsxRyHB4KxpHCNT2aQK7pbntD8xR8STH7OM0X5Kx3Qw6v_t9z8uXD-7v1Ndt8vvq4frdhCKAVE7Jz3jTaV9CoShrR1rpuRNcKH0TPhZG8EpWRnTBtE8DXwfu69a53bacApDwnb065k8tL4z650WO2U8LD0tdq1Wij1GIzJ9tvHML8KAO3x7HtMrZ9Gttub9ZP38KyE4u5hD-PrEs_ba2lruzX3ZX9Lj-pzRaM3cl_eXmGWw</recordid><startdate>198706</startdate><enddate>198706</enddate><creator>Casy, A. F.</creator><creator>Iorio, M. A.</creator><creator>Madani, A. E.</creator><general>John Wiley & Sons, Ltd</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope></search><sort><creationdate>198706</creationdate><title>Stereochemical studies of 3-aryl-3-methylpiperidines of potential opioid ligand activities by high-resolution 1H and 13C NMR spectroscopy</title><author>Casy, A. F. ; Iorio, M. A. ; Madani, A. E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i1174-23dac987c51845392b67682db2ce2f0293052593d29b8e1c6ecc6bcafabd41133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>13C NMR</topic><topic>1H NMR</topic><topic>3-Aryl-3-methylpiperidines</topic><topic>Atomic and molecular physics</topic><topic>Barrier heights (internal rotation, inversion, rotational isomerism, conformational dynamics)</topic><topic>conformational analysis</topic><topic>Exact sciences and technology</topic><topic>Molecular properties and interactions with photons</topic><topic>Physics</topic><topic>Properties of molecules and molecular ions</topic><topic>stereochemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Casy, A. F.</creatorcontrib><creatorcontrib>Iorio, M. A.</creatorcontrib><creatorcontrib>Madani, A. E.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><jtitle>Magnetic resonance in chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Casy, A. F.</au><au>Iorio, M. A.</au><au>Madani, A. E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereochemical studies of 3-aryl-3-methylpiperidines of potential opioid ligand activities by high-resolution 1H and 13C NMR spectroscopy</atitle><jtitle>Magnetic resonance in chemistry</jtitle><addtitle>Magn. Reson. Chem</addtitle><date>1987-06</date><risdate>1987</risdate><volume>25</volume><issue>6</issue><spage>524</spage><epage>530</epage><pages>524-530</pages><issn>0749-1581</issn><eissn>1097-458X</eissn><coden>MRCHEG</coden><abstract>The 1H (270, 400 MHz) and 13C (22.5, 67.5 MHz) NMR spectra of a series of 2,3‐3,5‐ and 3,6‐dimethyl‐3‐(m‐hydroxy‐m‐methoxy‐phenyl)piperidines of proven or potential opioid ligand activity are reported. The data were analysed in terms of configuration and preferred conformation, and some key deductions were confirmed by NOED and 2D COSY experiments. In the 3,5‐dimethyl derivatives, isomers with preferred axial or equatorial 3‐aryl substituents were identified.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><doi>10.1002/mrc.1260250614</doi><tpages>7</tpages></addata></record> |
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| ispartof | Magnetic resonance in chemistry, 1987-06, Vol.25 (6), p.524-530 |
| issn | 0749-1581 1097-458X |
| language | eng |
| recordid | cdi_pascalfrancis_primary_7487944 |
| source | Wiley Online Library All Journals |
| subjects | 13C NMR 1H NMR 3-Aryl-3-methylpiperidines Atomic and molecular physics Barrier heights (internal rotation, inversion, rotational isomerism, conformational dynamics) conformational analysis Exact sciences and technology Molecular properties and interactions with photons Physics Properties of molecules and molecular ions stereochemistry |
| title | Stereochemical studies of 3-aryl-3-methylpiperidines of potential opioid ligand activities by high-resolution 1H and 13C NMR spectroscopy |
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