Octahydrobenzo[g]quinolines: potent dopamine agonists which show the relationship between ergolines and apomorphine
A synthesis of all four diastereoisomeric 3-(tert-butoxycarbonyl)-1,6-dimethoxyoctahydrobenzo[g]quinolines 13a-d is presented. The two trans isomers 13b and 13c have been converted to tricyclic analogues 20 (CV 205-502) and 26 (205-503) of the potent dopaminomimetic ergolines CQ 32-084 and pergolide...
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| Veröffentlicht in: | Journal of medicinal chemistry 1985-03, Vol.28 (3), p.367-375 |
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| container_end_page | 375 |
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| container_issue | 3 |
| container_start_page | 367 |
| container_title | Journal of medicinal chemistry |
| container_volume | 28 |
| creator | Nordmann, Rene Petcher, Trevor J |
| description | A synthesis of all four diastereoisomeric 3-(tert-butoxycarbonyl)-1,6-dimethoxyoctahydrobenzo[g]quinolines 13a-d is presented. The two trans isomers 13b and 13c have been converted to tricyclic analogues 20 (CV 205-502) and 26 (205-503) of the potent dopaminomimetic ergolines CQ 32-084 and pergolide, respectively. These two compounds combine the essential moiety of apomorphine with the important 8-substituents of ergolines. Preliminary pharmacological evaluation of 20 and 26 suggests that these novel dopamine agonists combine the specificity of apomorphine with the potency, long duration of action, and good oral activity of the ergolines. |
| doi_str_mv | 10.1021/jm00381a017 |
| format | Article |
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The two trans isomers 13b and 13c have been converted to tricyclic analogues 20 (CV 205-502) and 26 (205-503) of the potent dopaminomimetic ergolines CQ 32-084 and pergolide, respectively. These two compounds combine the essential moiety of apomorphine with the important 8-substituents of ergolines. Preliminary pharmacological evaluation of 20 and 26 suggests that these novel dopamine agonists combine the specificity of apomorphine with the potency, long duration of action, and good oral activity of the ergolines.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00381a017</identifier><identifier>PMID: 3973904</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Apomorphine - pharmacology ; Chemistry ; Ergolines - pharmacology ; Exact sciences and technology ; Female ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Male ; Organic chemistry ; Pregnancy ; Preparations and properties ; Quinolines - chemical synthesis ; Quinolines - pharmacology ; Rats ; Receptors, Dopamine - drug effects ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 1985-03, Vol.28 (3), p.367-375</ispartof><rights>1985 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a414t-43098ac17b73f51325a9e3a15f435f7b42779f04258a7256d2e58c394a1fab133</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/jm00381a017$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00381a017$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=9042244$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3973904$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nordmann, Rene</creatorcontrib><creatorcontrib>Petcher, Trevor J</creatorcontrib><title>Octahydrobenzo[g]quinolines: potent dopamine agonists which show the relationship between ergolines and apomorphine</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A synthesis of all four diastereoisomeric 3-(tert-butoxycarbonyl)-1,6-dimethoxyoctahydrobenzo[g]quinolines 13a-d is presented. The two trans isomers 13b and 13c have been converted to tricyclic analogues 20 (CV 205-502) and 26 (205-503) of the potent dopaminomimetic ergolines CQ 32-084 and pergolide, respectively. These two compounds combine the essential moiety of apomorphine with the important 8-substituents of ergolines. Preliminary pharmacological evaluation of 20 and 26 suggests that these novel dopamine agonists combine the specificity of apomorphine with the potency, long duration of action, and good oral activity of the ergolines.</description><subject>Animals</subject><subject>Apomorphine - pharmacology</subject><subject>Chemistry</subject><subject>Ergolines - pharmacology</subject><subject>Exact sciences and technology</subject><subject>Female</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Male</subject><subject>Organic chemistry</subject><subject>Pregnancy</subject><subject>Preparations and properties</subject><subject>Quinolines - chemical synthesis</subject><subject>Quinolines - pharmacology</subject><subject>Rats</subject><subject>Receptors, Dopamine - drug effects</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1985</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0c-L1DAUB_AgLuu4evIs5CB6kK752bR7k8FfMLCurieR8Nqm04xt0k1axt2_3iwdBg8LngLvfXgvfB9CLyg5p4TRd7uBEF5QIFQ9QisqGclEQcRjtCKEsYzljD9BT2PckeQo46folJeKl0SsULysJ-hum-Ar4-78z-2vm9k631tn4gUe_WTchBs_wpAqGLbe2ThFvO9s3eHY-T2eOoOD6WGy3sXOjrgy094Yh03YLnMwuAbD6Acfxi4VnqGTFvponh_eM_Tj44fr9edsc_npy_r9JgNBxZQJTsoCaqoqxVtJOZNQGg5UtoLLVlWCKVW2RDBZgGIyb5iRRc1LAbSFinJ-hl4vc8fgb2YTJz3YWJu-B2f8HLXKCVGqIP-FNO2QNC8TfLvAOvgYg2n1GOwA4VZTou9vof-5RdIvD2PnajDN0R7CT_1Xhz7EGvo2gKttPLJEGBP3LFtYSt78ObYh_Na54krq66_f9fpqU1zx9Tctk3-zeKij3vk5uBTygx_8CzvXrfg</recordid><startdate>198503</startdate><enddate>198503</enddate><creator>Nordmann, Rene</creator><creator>Petcher, Trevor J</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>7TK</scope><scope>7X8</scope></search><sort><creationdate>198503</creationdate><title>Octahydrobenzo[g]quinolines: potent dopamine agonists which show the relationship between ergolines and apomorphine</title><author>Nordmann, Rene ; Petcher, Trevor J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a414t-43098ac17b73f51325a9e3a15f435f7b42779f04258a7256d2e58c394a1fab133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1985</creationdate><topic>Animals</topic><topic>Apomorphine - pharmacology</topic><topic>Chemistry</topic><topic>Ergolines - pharmacology</topic><topic>Exact sciences and technology</topic><topic>Female</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Male</topic><topic>Organic chemistry</topic><topic>Pregnancy</topic><topic>Preparations and properties</topic><topic>Quinolines - chemical synthesis</topic><topic>Quinolines - pharmacology</topic><topic>Rats</topic><topic>Receptors, Dopamine - drug effects</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nordmann, Rene</creatorcontrib><creatorcontrib>Petcher, Trevor J</creatorcontrib><collection>Istex</collection><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>Neurosciences 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>Nordmann, Rene</au><au>Petcher, Trevor J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Octahydrobenzo[g]quinolines: potent dopamine agonists which show the relationship between ergolines and apomorphine</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1985-03</date><risdate>1985</risdate><volume>28</volume><issue>3</issue><spage>367</spage><epage>375</epage><pages>367-375</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>A synthesis of all four diastereoisomeric 3-(tert-butoxycarbonyl)-1,6-dimethoxyoctahydrobenzo[g]quinolines 13a-d is presented. The two trans isomers 13b and 13c have been converted to tricyclic analogues 20 (CV 205-502) and 26 (205-503) of the potent dopaminomimetic ergolines CQ 32-084 and pergolide, respectively. These two compounds combine the essential moiety of apomorphine with the important 8-substituents of ergolines. Preliminary pharmacological evaluation of 20 and 26 suggests that these novel dopamine agonists combine the specificity of apomorphine with the potency, long duration of action, and good oral activity of the ergolines.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>3973904</pmid><doi>10.1021/jm00381a017</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1985-03, Vol.28 (3), p.367-375 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_76007780 |
| source | ACS Publications; MEDLINE |
| subjects | Animals Apomorphine - pharmacology Chemistry Ergolines - pharmacology Exact sciences and technology Female Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Male Organic chemistry Pregnancy Preparations and properties Quinolines - chemical synthesis Quinolines - pharmacology Rats Receptors, Dopamine - drug effects Structure-Activity Relationship |
| title | Octahydrobenzo[g]quinolines: potent dopamine agonists which show the relationship between ergolines and apomorphine |
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