Assessment of a potential dopaminergic prodrug moiety in several ring systems
The ortho hydroxy/methyl, hydroxy/hydroxymethyl, hydroxy/formyl, and hydroxy/carboxy substitution patterns, some of which confer dopaminergic agonist effects upon 2-aminotetralin ring systems, have been incorporated into beta-phenethylamine, 2-aminoindan, and trans-octahydrobenzo[f]quinoline rings....
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| Veröffentlicht in: | Journal of medicinal chemistry 1986-10, Vol.29 (10), p.2016-2020 |
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| container_issue | 10 |
| container_start_page | 2016 |
| container_title | Journal of medicinal chemistry |
| container_volume | 29 |
| creator | Cannon, Joseph G Furlano, David C Dushin, Russell G Chang, Yu An Baird, Stephen R Soliman, Laila N Flynn, Jan R Long, John Paul Bhatnagar, Ranbir K |
| description | The ortho hydroxy/methyl, hydroxy/hydroxymethyl, hydroxy/formyl, and hydroxy/carboxy substitution patterns, some of which confer dopaminergic agonist effects upon 2-aminotetralin ring systems, have been incorporated into beta-phenethylamine, 2-aminoindan, and trans-octahydrobenzo[f]quinoline rings. Certain of the 2-aminoindan derivatives displayed pharmacologic properties consistent with their being dopaminergic agonists. The beta-phenethylamine derivative did not show any significant dopamine-like activity. The 7-hydroxy-8-methyloctahydrobenzo[f]quinoline derivative 4a was a moderately potent, short-acting DA2 receptor antagonist. All of the carboxylic acid derivatives were inert. Of the ortho hydroxy/methyl derivatives, only the 5-hydroxy-6-methyl-2-aminotetralin derivative displayed pharmacological properties consistent with its being a dopaminergic prodrug. It is concluded that 5-hydroxy-6-methyl-2-(di-n-propylamino)tetralin (1a) is structurally unique for a dopaminergic drug. |
| doi_str_mv | 10.1021/jm00160a036 |
| format | Article |
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Certain of the 2-aminoindan derivatives displayed pharmacologic properties consistent with their being dopaminergic agonists. The beta-phenethylamine derivative did not show any significant dopamine-like activity. The 7-hydroxy-8-methyloctahydrobenzo[f]quinoline derivative 4a was a moderately potent, short-acting DA2 receptor antagonist. All of the carboxylic acid derivatives were inert. Of the ortho hydroxy/methyl derivatives, only the 5-hydroxy-6-methyl-2-aminotetralin derivative displayed pharmacological properties consistent with its being a dopaminergic prodrug. 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Med. Chem</addtitle><description>The ortho hydroxy/methyl, hydroxy/hydroxymethyl, hydroxy/formyl, and hydroxy/carboxy substitution patterns, some of which confer dopaminergic agonist effects upon 2-aminotetralin ring systems, have been incorporated into beta-phenethylamine, 2-aminoindan, and trans-octahydrobenzo[f]quinoline rings. Certain of the 2-aminoindan derivatives displayed pharmacologic properties consistent with their being dopaminergic agonists. The beta-phenethylamine derivative did not show any significant dopamine-like activity. The 7-hydroxy-8-methyloctahydrobenzo[f]quinoline derivative 4a was a moderately potent, short-acting DA2 receptor antagonist. All of the carboxylic acid derivatives were inert. Of the ortho hydroxy/methyl derivatives, only the 5-hydroxy-6-methyl-2-aminotetralin derivative displayed pharmacological properties consistent with its being a dopaminergic prodrug. It is concluded that 5-hydroxy-6-methyl-2-(di-n-propylamino)tetralin (1a) is structurally unique for a dopaminergic drug.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cats</subject><subject>General pharmacology</subject><subject>Indans - pharmacology</subject><subject>Indenes - pharmacology</subject><subject>Medical sciences</subject><subject>Naphthalenes - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Phenethylamines - pharmacology</subject><subject>Physicochemical properties. Structure-activity relationships</subject><subject>Quinolines - pharmacology</subject><subject>Rats</subject><subject>Receptors, Dopamine - drug effects</subject><subject>Structure-Activity Relationship</subject><subject>Tetrahydronaphthalenes - pharmacology</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1986</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1rGzEQhkVpSJ2kp54LOpTmUDYZSauPPQYnbRIcGohDj0KWtUbufria3RD_-yrYmB56moH34Z3hIeQTgwsGnF2uWwCmwIFQ78iESQ5FaaB8TyYAnBdccfGBnCCuAUAwLo7JsdCKCQ4T8nCFGBDb0A20r6mjm37Ie3QNXfYb18YupFX0dJP6ZRpXtO1jGLY0dhTDS0gZS7FbUdziEFo8I0e1azB83M9T8vz9Zj69LWY_f9xNr2aFE0YMRRVKqIUrfZCm9IbpWvNyISXXugJXec1rkKXxysNCMqYYeG9C7YVUlTEqiFPyddeb3_ozBhxsG9GHpnFd6Ee0WoOSgpkMftuBPvWIKdR2k2Lr0tYysG_y7D_yMv15Xzsu2rA8sHtbOf-yzx1619TJdT7iATOgpanejhY7LGYpr4fYpd9WaaGlnT8-2fvp_Prh9tfMPmX-fMc7j3bdj6nL7v774F8zU5HH</recordid><startdate>19861001</startdate><enddate>19861001</enddate><creator>Cannon, Joseph G</creator><creator>Furlano, David C</creator><creator>Dushin, Russell G</creator><creator>Chang, Yu An</creator><creator>Baird, Stephen R</creator><creator>Soliman, Laila N</creator><creator>Flynn, Jan R</creator><creator>Long, John Paul</creator><creator>Bhatnagar, Ranbir K</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>7X8</scope></search><sort><creationdate>19861001</creationdate><title>Assessment of a potential dopaminergic prodrug moiety in several ring systems</title><author>Cannon, Joseph G ; Furlano, David C ; Dushin, Russell G ; Chang, Yu An ; Baird, Stephen R ; Soliman, Laila N ; Flynn, Jan R ; Long, John Paul ; Bhatnagar, Ranbir K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a383t-9e40f3a4ce584c817f724b5527790a9c72f0548c6c0b511610cc8efc3569886e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1986</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cats</topic><topic>General pharmacology</topic><topic>Indans - pharmacology</topic><topic>Indenes - pharmacology</topic><topic>Medical sciences</topic><topic>Naphthalenes - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Phenethylamines - pharmacology</topic><topic>Physicochemical properties. Structure-activity relationships</topic><topic>Quinolines - pharmacology</topic><topic>Rats</topic><topic>Receptors, Dopamine - drug effects</topic><topic>Structure-Activity Relationship</topic><topic>Tetrahydronaphthalenes - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cannon, Joseph G</creatorcontrib><creatorcontrib>Furlano, David C</creatorcontrib><creatorcontrib>Dushin, Russell G</creatorcontrib><creatorcontrib>Chang, Yu An</creatorcontrib><creatorcontrib>Baird, Stephen R</creatorcontrib><creatorcontrib>Soliman, Laila N</creatorcontrib><creatorcontrib>Flynn, Jan R</creatorcontrib><creatorcontrib>Long, John Paul</creatorcontrib><creatorcontrib>Bhatnagar, Ranbir K</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>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cannon, Joseph G</au><au>Furlano, David C</au><au>Dushin, Russell G</au><au>Chang, Yu An</au><au>Baird, Stephen R</au><au>Soliman, Laila N</au><au>Flynn, Jan R</au><au>Long, John Paul</au><au>Bhatnagar, Ranbir K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Assessment of a potential dopaminergic prodrug moiety in several ring systems</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. 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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Biological and medical sciences Cats General pharmacology Indans - pharmacology Indenes - pharmacology Medical sciences Naphthalenes - pharmacology Pharmacology. Drug treatments Phenethylamines - pharmacology Physicochemical properties. Structure-activity relationships Quinolines - pharmacology Rats Receptors, Dopamine - drug effects Structure-Activity Relationship Tetrahydronaphthalenes - pharmacology |
| title | Assessment of a potential dopaminergic prodrug moiety in several ring systems |
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