Correlation between affinity toward adrenergic receptors and approximate electrostatic potentials of phenylethylamine derivatives. 1. Effects of the side chain
The molecular electrostatic potential (VN) in the region of the nitrogen lone pair of a series of substituted propylamines is used in a correlation with the dissociation constants of parent phenylethylamine-type ligands obtained on beta-adrenoceptors by Bilezikian et al. It is shown that VN is a mor...
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| Veröffentlicht in: | Journal of medicinal chemistry 1982-12, Vol.25 (12), p.1413-1417 |
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| container_end_page | 1417 |
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| container_issue | 12 |
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| container_title | Journal of medicinal chemistry |
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| creator | Solmajer, Tomaz Lukovits, Istvan Hadzi, Dusan |
| description | The molecular electrostatic potential (VN) in the region of the nitrogen lone pair of a series of substituted propylamines is used in a correlation with the dissociation constants of parent phenylethylamine-type ligands obtained on beta-adrenoceptors by Bilezikian et al. It is shown that VN is a more effective index for quantitative structure-activity relationship studies than an optimal set of substituent constants used in additive, linear models. No significant correlation between the total electronic charge on the nitrogen and the binding potencies was obtained in the examined series. Protonation energies of the propylamines have been computed, but no meaningful correlation with the dissociation constants was obtained. |
| doi_str_mv | 10.1021/jm00354a004 |
| format | Article |
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Effects of the side chain</title><source>MEDLINE</source><source>American Chemical Society (ACS) Journals</source><creator>Solmajer, Tomaz ; Lukovits, Istvan ; Hadzi, Dusan</creator><creatorcontrib>Solmajer, Tomaz ; Lukovits, Istvan ; Hadzi, Dusan</creatorcontrib><description>The molecular electrostatic potential (VN) in the region of the nitrogen lone pair of a series of substituted propylamines is used in a correlation with the dissociation constants of parent phenylethylamine-type ligands obtained on beta-adrenoceptors by Bilezikian et al. It is shown that VN is a more effective index for quantitative structure-activity relationship studies than an optimal set of substituent constants used in additive, linear models. No significant correlation between the total electronic charge on the nitrogen and the binding potencies was obtained in the examined series. Protonation energies of the propylamines have been computed, but no meaningful correlation with the dissociation constants was obtained.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00354a004</identifier><identifier>PMID: 7154001</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>adrenergic ; beta -phenylethylamine ; Chemical Phenomena ; Chemistry, Physical ; Electrochemistry ; Molecular Conformation ; Phenethylamines - metabolism ; Receptors, Adrenergic - metabolism ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 1982-12, Vol.25 (12), p.1413-1417</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a385t-cffcf884c926b743d0cd65b6f4aa5d1ee00ba04710122ada078c0067baa96dd03</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00354a004$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00354a004$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7154001$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Solmajer, Tomaz</creatorcontrib><creatorcontrib>Lukovits, Istvan</creatorcontrib><creatorcontrib>Hadzi, Dusan</creatorcontrib><title>Correlation between affinity toward adrenergic receptors and approximate electrostatic potentials of phenylethylamine derivatives. 1. Effects of the side chain</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The molecular electrostatic potential (VN) in the region of the nitrogen lone pair of a series of substituted propylamines is used in a correlation with the dissociation constants of parent phenylethylamine-type ligands obtained on beta-adrenoceptors by Bilezikian et al. It is shown that VN is a more effective index for quantitative structure-activity relationship studies than an optimal set of substituent constants used in additive, linear models. No significant correlation between the total electronic charge on the nitrogen and the binding potencies was obtained in the examined series. Protonation energies of the propylamines have been computed, but no meaningful correlation with the dissociation constants was obtained.</description><subject>adrenergic</subject><subject>beta -phenylethylamine</subject><subject>Chemical Phenomena</subject><subject>Chemistry, Physical</subject><subject>Electrochemistry</subject><subject>Molecular Conformation</subject><subject>Phenethylamines - metabolism</subject><subject>Receptors, Adrenergic - metabolism</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1982</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkb1vFDEQxVcIFI5ARY3kCgq0x9jr_UiJTvmSIoGUQEFjzdpjzseud7F9Se6v4V_F4U4RBRLVFO83bzTvFcVrDksOgn_YjABVLRFAPikWvBZQyg7k02IBIEQpGlE9L17EuIHMcVEdFUctryUAXxS_VlMINGByk2c9pTsiz9Ba513asTTdYTAMTSBP4bvTLJCmOU0hMvRZmOcw3bsREzEaSKcwxZS9NJunRD45HCKbLJvX5HcDpfVuwNF5YoaCu83gLcUl40t2am3e_sOmNbHoDDG9RudfFs9sNqFXh3lcfDk7vVldlFefzi9XH69KrLo6ldpabbtO6hPR9K2sDGjT1H1jJWJtOBFAjyBbDlwINAhtpwGatkc8aYyB6rh4u_fND_3cUkxqdFHTMKCnaRtVB6Juhaz_C_KqbtqKVxl8vwd1DiUGsmoOOamwUxzUQ2_qr94y_eZgu-1HMo_soaisl3vdxUT3jzKGHyqfa2t18_laNdfnF-Kr_KbOMv9uz6OOajNtg8_p_fPybx7Bsqo</recordid><startdate>198212</startdate><enddate>198212</enddate><creator>Solmajer, Tomaz</creator><creator>Lukovits, Istvan</creator><creator>Hadzi, Dusan</creator><general>American Chemical Society</general><scope>BSCLL</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>8FD</scope><scope>FR3</scope><scope>M7Z</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>198212</creationdate><title>Correlation between affinity toward adrenergic receptors and approximate electrostatic potentials of phenylethylamine derivatives. 1. Effects of the side chain</title><author>Solmajer, Tomaz ; Lukovits, Istvan ; Hadzi, Dusan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a385t-cffcf884c926b743d0cd65b6f4aa5d1ee00ba04710122ada078c0067baa96dd03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1982</creationdate><topic>adrenergic</topic><topic>beta -phenylethylamine</topic><topic>Chemical Phenomena</topic><topic>Chemistry, Physical</topic><topic>Electrochemistry</topic><topic>Molecular Conformation</topic><topic>Phenethylamines - metabolism</topic><topic>Receptors, Adrenergic - metabolism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Solmajer, Tomaz</creatorcontrib><creatorcontrib>Lukovits, Istvan</creatorcontrib><creatorcontrib>Hadzi, Dusan</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biochemistry Abstracts 1</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Solmajer, Tomaz</au><au>Lukovits, Istvan</au><au>Hadzi, Dusan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Correlation between affinity toward adrenergic receptors and approximate electrostatic potentials of phenylethylamine derivatives. 1. Effects of the side chain</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1982-12</date><risdate>1982</risdate><volume>25</volume><issue>12</issue><spage>1413</spage><epage>1417</epage><pages>1413-1417</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>The molecular electrostatic potential (VN) in the region of the nitrogen lone pair of a series of substituted propylamines is used in a correlation with the dissociation constants of parent phenylethylamine-type ligands obtained on beta-adrenoceptors by Bilezikian et al. It is shown that VN is a more effective index for quantitative structure-activity relationship studies than an optimal set of substituent constants used in additive, linear models. No significant correlation between the total electronic charge on the nitrogen and the binding potencies was obtained in the examined series. Protonation energies of the propylamines have been computed, but no meaningful correlation with the dissociation constants was obtained.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>7154001</pmid><doi>10.1021/jm00354a004</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1982-12, Vol.25 (12), p.1413-1417 |
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| language | eng |
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| source | MEDLINE; American Chemical Society (ACS) Journals |
| subjects | adrenergic beta -phenylethylamine Chemical Phenomena Chemistry, Physical Electrochemistry Molecular Conformation Phenethylamines - metabolism Receptors, Adrenergic - metabolism Structure-Activity Relationship |
| title | Correlation between affinity toward adrenergic receptors and approximate electrostatic potentials of phenylethylamine derivatives. 1. Effects of the side chain |
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