Synthesis and pharmacology of some 2-aminotetralins. Dopamine receptor agonists
A series of 2-amino-1,2,3,4-tetrahydronaphthalene compounds bearing substituents on the nitrogen and in the aromatic ring was synthesized from beta-tetralone intermediates. Compounds were screened in vivo for dopaminergic activity using tests in which apomorphine was especially active. It was found...
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| Veröffentlicht in: | Journal of medicinal chemistry 1975-04, Vol.18 (4), p.362-367 |
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| container_end_page | 367 |
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| container_issue | 4 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 18 |
| creator | McDermed, John D McKenzie, Gerald M Phillips, Arthur P |
| description | A series of 2-amino-1,2,3,4-tetrahydronaphthalene compounds bearing substituents on the nitrogen and in the aromatic ring was synthesized from beta-tetralone intermediates. Compounds were screened in vivo for dopaminergic activity using tests in which apomorphine was especially active. It was found that apparent dopaminergic activity is inherent in 2-dialkylaminotetralins, the dipropylamine substitution being the most consistently productive amine group studies. Activity was greatly enhanced by proper substitution in the aromatic ring. The 5,6-dihydroxy group was the best potentiating group found. These data support the idea that the extended conformation for the phenylethylamine moiety of ampmorphine and dopamine is favorable for dopaminergic agonist activity. They also suggest that an unetherified catechol group may not be essential for such activity. |
| doi_str_mv | 10.1021/jm00238a008 |
| format | Article |
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These data support the idea that the extended conformation for the phenylethylamine moiety of ampmorphine and dopamine is favorable for dopaminergic agonist activity. They also suggest that an unetherified catechol group may not be essential for such activity.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00238a008</identifier><identifier>PMID: 1168259</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amines - chemical synthesis ; Amines - pharmacology ; Animals ; Chloralose - antagonists & inhibitors ; Dogs ; Dopamine - physiology ; Electromyography ; Humans ; Male ; Naphthalenes - chemical synthesis ; Naphthalenes - pharmacology ; Rats ; Receptors, Drug ; Reserpine - antagonists & inhibitors ; Stereotyped Behavior - drug effects ; Tremor - prevention & control ; Vomiting - chemically induced</subject><ispartof>Journal of medicinal chemistry, 1975-04, Vol.18 (4), p.362-367</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a354t-43627f02010d6b4b00bf13797cc118d18111654f496292223da3645ff782ef1e3</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/jm00238a008$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00238a008$$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/1168259$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>McDermed, John D</creatorcontrib><creatorcontrib>McKenzie, Gerald M</creatorcontrib><creatorcontrib>Phillips, Arthur P</creatorcontrib><title>Synthesis and pharmacology of some 2-aminotetralins. Dopamine receptor agonists</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of 2-amino-1,2,3,4-tetrahydronaphthalene compounds bearing substituents on the nitrogen and in the aromatic ring was synthesized from beta-tetralone intermediates. Compounds were screened in vivo for dopaminergic activity using tests in which apomorphine was especially active. It was found that apparent dopaminergic activity is inherent in 2-dialkylaminotetralins, the dipropylamine substitution being the most consistently productive amine group studies. Activity was greatly enhanced by proper substitution in the aromatic ring. The 5,6-dihydroxy group was the best potentiating group found. These data support the idea that the extended conformation for the phenylethylamine moiety of ampmorphine and dopamine is favorable for dopaminergic agonist activity. They also suggest that an unetherified catechol group may not be essential for such activity.</description><subject>Amines - chemical synthesis</subject><subject>Amines - pharmacology</subject><subject>Animals</subject><subject>Chloralose - antagonists & inhibitors</subject><subject>Dogs</subject><subject>Dopamine - physiology</subject><subject>Electromyography</subject><subject>Humans</subject><subject>Male</subject><subject>Naphthalenes - chemical synthesis</subject><subject>Naphthalenes - pharmacology</subject><subject>Rats</subject><subject>Receptors, Drug</subject><subject>Reserpine - antagonists & inhibitors</subject><subject>Stereotyped Behavior - drug effects</subject><subject>Tremor - prevention & control</subject><subject>Vomiting - chemically induced</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1975</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1Lw0AQxRdRaq2ePAs56UFSZ2c3X0ep3xSqtOJx2Sa7NTXJxt0E7H9vSop68DTw3o83M4-QUwpjCkiv1iUAslgCxHtkSAMEn8fA98mw09HHENkhOXJuDQCMIhuQAaVhjEEyJLP5pmrelcudJ6vMq9-lLWVqCrPaeEZ7zpTKQ1-WeWUa1VhZ5JUbezem3krKsypVdWOsJ1emyl3jjsmBloVTJ7s5Iq93t4vJgz-d3T9Orqe-ZAFvfM5CjDQgUMjCJV8CLDVlURKlKaVxRmPaXRhwzZMQE0RkmWQhD7SOYlSaKjYi531ubc1nq1wjytylqihkpUzrRIxRwjFiHXjZg6k1zlmlRW3zUtqNoCC29Yk_9XX02S62XZYq-2X7vjrf7_3uV_X1Y0v7IcKIRYFYPM_F9O1pTsMpEy8df9HzMnVibVpbdaX8u_kb5gmE4Q</recordid><startdate>19750401</startdate><enddate>19750401</enddate><creator>McDermed, John D</creator><creator>McKenzie, Gerald M</creator><creator>Phillips, Arthur P</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>7X8</scope></search><sort><creationdate>19750401</creationdate><title>Synthesis and pharmacology of some 2-aminotetralins. 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Dopamine receptor agonists</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1975-04-01</date><risdate>1975</risdate><volume>18</volume><issue>4</issue><spage>362</spage><epage>367</epage><pages>362-367</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>A series of 2-amino-1,2,3,4-tetrahydronaphthalene compounds bearing substituents on the nitrogen and in the aromatic ring was synthesized from beta-tetralone intermediates. Compounds were screened in vivo for dopaminergic activity using tests in which apomorphine was especially active. It was found that apparent dopaminergic activity is inherent in 2-dialkylaminotetralins, the dipropylamine substitution being the most consistently productive amine group studies. Activity was greatly enhanced by proper substitution in the aromatic ring. The 5,6-dihydroxy group was the best potentiating group found. These data support the idea that the extended conformation for the phenylethylamine moiety of ampmorphine and dopamine is favorable for dopaminergic agonist activity. They also suggest that an unetherified catechol group may not be essential for such activity.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>1168259</pmid><doi>10.1021/jm00238a008</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1975-04, Vol.18 (4), p.362-367 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Amines - chemical synthesis Amines - pharmacology Animals Chloralose - antagonists & inhibitors Dogs Dopamine - physiology Electromyography Humans Male Naphthalenes - chemical synthesis Naphthalenes - pharmacology Rats Receptors, Drug Reserpine - antagonists & inhibitors Stereotyped Behavior - drug effects Tremor - prevention & control Vomiting - chemically induced |
| title | Synthesis and pharmacology of some 2-aminotetralins. Dopamine receptor agonists |
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