6-hydroxy-3-n-propyl-2,3,4,5-tetrahydro-1H-3-benzazepine and analogs : new centrally acting 5-HT1A receptor agonists
The ring-closed phenylethylamine analogue 6-hydroxy-3-n-propyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1) is a 5-HT1A receptor agonist of moderate potency, according to both in vivo biochemical data and in vitro binding data. The active compounds of this series also induce the 5-HT behavioral syndrome....
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| Veröffentlicht in: | Journal of medicinal chemistry 1992-10, Vol.35 (22), p.3984-3990 |
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| container_end_page | 3990 |
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| container_issue | 22 |
| container_start_page | 3984 |
| container_title | Journal of medicinal chemistry |
| container_volume | 35 |
| creator | WIKSTRÖM, H ANDERSSON, B ELEBRING, T LAGERKVIST, S HALLNEMO, G PETTERSSON, I JOVAL, P.-Å SVENSSON, K EKMAN, A CARLSSON, A |
| description | The ring-closed phenylethylamine analogue 6-hydroxy-3-n-propyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1) is a 5-HT1A receptor agonist of moderate potency, according to both in vivo biochemical data and in vitro binding data. The active compounds of this series also induce the 5-HT behavioral syndrome. Molecular modeling studies were performed with molecular mechanics calculations, and a tentative explanation for the relatively low potency of these serotonergic benzazepines is provided. |
| doi_str_mv | 10.1021/jm00100a002 |
| format | Article |
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The active compounds of this series also induce the 5-HT behavioral syndrome. Molecular modeling studies were performed with molecular mechanics calculations, and a tentative explanation for the relatively low potency of these serotonergic benzazepines is provided.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00100a002</identifier><identifier>PMID: 1433207</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Benzazepines - chemistry ; Benzazepines - pharmacology ; Binding, Competitive ; Biological and medical sciences ; Brain - drug effects ; Brain - metabolism ; Dopamine - biosynthesis ; Feedback ; In Vitro Techniques ; Male ; Medical sciences ; Models, Molecular ; Molecular Conformation ; Motor Activity - drug effects ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Norepinephrine - biosynthesis ; Pharmacology. Drug treatments ; Radioligand Assay ; Rats ; Rats, Sprague-Dawley ; Receptors, Serotonin - drug effects ; Receptors, Serotonin - metabolism ; Serotonin - biosynthesis ; Serotonin Receptor Agonists - chemistry ; Serotonin Receptor Agonists - pharmacology ; Serotoninergic system ; Structure-Activity Relationship ; Thermodynamics</subject><ispartof>Journal of medicinal chemistry, 1992-10, Vol.35 (22), p.3984-3990</ispartof><rights>1993 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=4524577$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1433207$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>WIKSTRÖM, H</creatorcontrib><creatorcontrib>ANDERSSON, B</creatorcontrib><creatorcontrib>ELEBRING, T</creatorcontrib><creatorcontrib>LAGERKVIST, S</creatorcontrib><creatorcontrib>HALLNEMO, G</creatorcontrib><creatorcontrib>PETTERSSON, I</creatorcontrib><creatorcontrib>JOVAL, P.-Å</creatorcontrib><creatorcontrib>SVENSSON, K</creatorcontrib><creatorcontrib>EKMAN, A</creatorcontrib><creatorcontrib>CARLSSON, A</creatorcontrib><title>6-hydroxy-3-n-propyl-2,3,4,5-tetrahydro-1H-3-benzazepine and analogs : new centrally acting 5-HT1A receptor agonists</title><title>Journal of medicinal chemistry</title><addtitle>J Med Chem</addtitle><description>The ring-closed phenylethylamine analogue 6-hydroxy-3-n-propyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1) is a 5-HT1A receptor agonist of moderate potency, according to both in vivo biochemical data and in vitro binding data. The active compounds of this series also induce the 5-HT behavioral syndrome. Molecular modeling studies were performed with molecular mechanics calculations, and a tentative explanation for the relatively low potency of these serotonergic benzazepines is provided.</description><subject>Animals</subject><subject>Benzazepines - chemistry</subject><subject>Benzazepines - pharmacology</subject><subject>Binding, Competitive</subject><subject>Biological and medical sciences</subject><subject>Brain - drug effects</subject><subject>Brain - metabolism</subject><subject>Dopamine - biosynthesis</subject><subject>Feedback</subject><subject>In Vitro Techniques</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Motor Activity - drug effects</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Norepinephrine - biosynthesis</subject><subject>Pharmacology. Drug treatments</subject><subject>Radioligand Assay</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><subject>Receptors, Serotonin - drug effects</subject><subject>Receptors, Serotonin - metabolism</subject><subject>Serotonin - biosynthesis</subject><subject>Serotonin Receptor Agonists - chemistry</subject><subject>Serotonin Receptor Agonists - pharmacology</subject><subject>Serotoninergic system</subject><subject>Structure-Activity Relationship</subject><subject>Thermodynamics</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kMFOwzAMQCMEGmNw4ozUA-K0gBO3TcdtmoAhTeIyzlWWuqMoS0vTCbqvJ0DFwbLl92TLZuxSwK0AKe7edwACQAPIIzYWiQQeZxAfs3HoSC5TiafszPt3AEAhccRGIkaUoMasS_lbX7T1V8-RO960ddNbLqc4jacJ76hr9S_nYhmEDbmDPlBTOYq0K0JoW299dB85-owMuaBb20fadJXbRglfrsU8aslQ09VtpLe1q3znz9lJqa2niyFP2Ovjw3qx5KuXp-fFfMUbiUnHy1JlJSWQZQo1Iho1Sw2VJE2mikyYUplU6Z8yLChmCRgDQlEmNwUWJRFO2M3f3HDWx558l-8qb8ha7aje-1yhnCHEIohXg7jf7KjIm7ba6bbPhzcFfj1w7Y22Zaudqfy_FicyTpTCb0XldUM</recordid><startdate>19921030</startdate><enddate>19921030</enddate><creator>WIKSTRÖM, H</creator><creator>ANDERSSON, B</creator><creator>ELEBRING, T</creator><creator>LAGERKVIST, S</creator><creator>HALLNEMO, G</creator><creator>PETTERSSON, I</creator><creator>JOVAL, P.-Å</creator><creator>SVENSSON, K</creator><creator>EKMAN, A</creator><creator>CARLSSON, A</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>19921030</creationdate><title>6-hydroxy-3-n-propyl-2,3,4,5-tetrahydro-1H-3-benzazepine and analogs : new centrally acting 5-HT1A receptor agonists</title><author>WIKSTRÖM, H ; ANDERSSON, B ; ELEBRING, T ; LAGERKVIST, S ; HALLNEMO, G ; PETTERSSON, I ; JOVAL, P.-Å ; SVENSSON, K ; EKMAN, A ; CARLSSON, A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p235t-ff78fe508873a333c796cefe2c87d81cf7c67a7d81eced950cc017e82bd3dfee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1992</creationdate><topic>Animals</topic><topic>Benzazepines - chemistry</topic><topic>Benzazepines - pharmacology</topic><topic>Binding, Competitive</topic><topic>Biological and medical sciences</topic><topic>Brain - drug effects</topic><topic>Brain - metabolism</topic><topic>Dopamine - biosynthesis</topic><topic>Feedback</topic><topic>In Vitro Techniques</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Motor Activity - drug effects</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Norepinephrine - biosynthesis</topic><topic>Pharmacology. Drug treatments</topic><topic>Radioligand Assay</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><topic>Receptors, Serotonin - drug effects</topic><topic>Receptors, Serotonin - metabolism</topic><topic>Serotonin - biosynthesis</topic><topic>Serotonin Receptor Agonists - chemistry</topic><topic>Serotonin Receptor Agonists - pharmacology</topic><topic>Serotoninergic system</topic><topic>Structure-Activity Relationship</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>WIKSTRÖM, H</creatorcontrib><creatorcontrib>ANDERSSON, B</creatorcontrib><creatorcontrib>ELEBRING, T</creatorcontrib><creatorcontrib>LAGERKVIST, S</creatorcontrib><creatorcontrib>HALLNEMO, G</creatorcontrib><creatorcontrib>PETTERSSON, I</creatorcontrib><creatorcontrib>JOVAL, P.-Å</creatorcontrib><creatorcontrib>SVENSSON, K</creatorcontrib><creatorcontrib>EKMAN, A</creatorcontrib><creatorcontrib>CARLSSON, A</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>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>WIKSTRÖM, H</au><au>ANDERSSON, B</au><au>ELEBRING, T</au><au>LAGERKVIST, S</au><au>HALLNEMO, G</au><au>PETTERSSON, I</au><au>JOVAL, P.-Å</au><au>SVENSSON, K</au><au>EKMAN, A</au><au>CARLSSON, A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>6-hydroxy-3-n-propyl-2,3,4,5-tetrahydro-1H-3-benzazepine and analogs : new centrally acting 5-HT1A receptor agonists</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J Med Chem</addtitle><date>1992-10-30</date><risdate>1992</risdate><volume>35</volume><issue>22</issue><spage>3984</spage><epage>3990</epage><pages>3984-3990</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The ring-closed phenylethylamine analogue 6-hydroxy-3-n-propyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1) is a 5-HT1A receptor agonist of moderate potency, according to both in vivo biochemical data and in vitro binding data. 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| ispartof | Journal of medicinal chemistry, 1992-10, Vol.35 (22), p.3984-3990 |
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| subjects | Animals Benzazepines - chemistry Benzazepines - pharmacology Binding, Competitive Biological and medical sciences Brain - drug effects Brain - metabolism Dopamine - biosynthesis Feedback In Vitro Techniques Male Medical sciences Models, Molecular Molecular Conformation Motor Activity - drug effects Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Norepinephrine - biosynthesis Pharmacology. Drug treatments Radioligand Assay Rats Rats, Sprague-Dawley Receptors, Serotonin - drug effects Receptors, Serotonin - metabolism Serotonin - biosynthesis Serotonin Receptor Agonists - chemistry Serotonin Receptor Agonists - pharmacology Serotoninergic system Structure-Activity Relationship Thermodynamics |
| title | 6-hydroxy-3-n-propyl-2,3,4,5-tetrahydro-1H-3-benzazepine and analogs : new centrally acting 5-HT1A receptor agonists |
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