Synthesis and biological activity of D3-trishomocubyl-4-amines
The D3-trishomocubyl system was prepared from tertiary pentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-ols 5 in one step by using a modified Ritter reaction yielding only one of the possible two geometrical isomers of 4-amino-3-alkyl (or aryl)-D3-trishomocubane (8). Promising antagonism of reserpin...
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| Veröffentlicht in: | Journal of medicinal chemistry 1991-02, Vol.34 (2), p.851-854 |
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| container_issue | 2 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 34 |
| creator | Oliver, Douglas W Dekker, Theodor G Snyckers, Friedrich O Fourie, Theunis G |
| description | The D3-trishomocubyl system was prepared from tertiary pentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-ols 5 in one step by using a modified Ritter reaction yielding only one of the possible two geometrical isomers of 4-amino-3-alkyl (or aryl)-D3-trishomocubane (8). Promising antagonism of reserpine-induced catalepsy was exhibited by these compounds which compared favorable with that of amantadine. Weak to mild anticholinergic properties were observed during the reduction of oxotremorine induced tremor and salivation procedure. Acute toxicities similar to that of amantadine were observed for some of these compounds. D3-Trishomocubyl-4-amines appeared as a promising new class of anti-Parkinson agents. |
| doi_str_mv | 10.1021/jm00106a053 |
| format | Article |
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Promising antagonism of reserpine-induced catalepsy was exhibited by these compounds which compared favorable with that of amantadine. Weak to mild anticholinergic properties were observed during the reduction of oxotremorine induced tremor and salivation procedure. Acute toxicities similar to that of amantadine were observed for some of these compounds. D3-Trishomocubyl-4-amines appeared as a promising new class of anti-Parkinson agents.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00106a053</identifier><identifier>PMID: 1995908</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Antiparkinson Agents - chemical synthesis ; Antiparkinson Agents - therapeutic use ; Antiparkinson Agents - toxicity ; Bridged-Ring Compounds - chemical synthesis ; Bridged-Ring Compounds - therapeutic use ; Bridged-Ring Compounds - toxicity ; Catalepsy - drug therapy ; Chemical Phenomena ; Chemistry ; Male ; Mice ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 1991-02, Vol.34 (2), p.851-854</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a354t-20310bcc653d81e82d1e378aeac48f653e1122d00f9853b262e8e0c42f4cd0cd3</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/jm00106a053$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00106a053$$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/1995908$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Oliver, Douglas W</creatorcontrib><creatorcontrib>Dekker, Theodor G</creatorcontrib><creatorcontrib>Snyckers, Friedrich O</creatorcontrib><creatorcontrib>Fourie, Theunis G</creatorcontrib><title>Synthesis and biological activity of D3-trishomocubyl-4-amines</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The D3-trishomocubyl system was prepared from tertiary pentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-ols 5 in one step by using a modified Ritter reaction yielding only one of the possible two geometrical isomers of 4-amino-3-alkyl (or aryl)-D3-trishomocubane (8). Promising antagonism of reserpine-induced catalepsy was exhibited by these compounds which compared favorable with that of amantadine. Weak to mild anticholinergic properties were observed during the reduction of oxotremorine induced tremor and salivation procedure. Acute toxicities similar to that of amantadine were observed for some of these compounds. D3-Trishomocubyl-4-amines appeared as a promising new class of anti-Parkinson agents.</description><subject>Animals</subject><subject>Antiparkinson Agents - chemical synthesis</subject><subject>Antiparkinson Agents - therapeutic use</subject><subject>Antiparkinson Agents - toxicity</subject><subject>Bridged-Ring Compounds - chemical synthesis</subject><subject>Bridged-Ring Compounds - therapeutic use</subject><subject>Bridged-Ring Compounds - toxicity</subject><subject>Catalepsy - drug therapy</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Male</subject><subject>Mice</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1991</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM9LwzAUx4Moc05PnoXePEj0JWm79CLIdP5gTGETvYU0SV1m24ymFfvf21FRD54evO-H7_e9L0LHBM4JUHKxLgAIxBIitoOGJKKAQw7hLhoCUIppTNk-OvB-DQCMUDZAA5IkUQJ8iC4XbVmvjLc-kKUOUuty92aVzAOpavth6zZwWXDNcF1Zv3KFU03a5jjEsrCl8YdoL5O5N0ffc4SepzfLyR2ePd7eT65mWLIorDHtciFVKo6Y5sRwqolhYy6NVCHPuq0hhFINkCU8Yml3seEGVEizUGlQmo3QWe-rKud9ZTKxqWwhq1YQENsSxJ8SOvqkpzdNWhj9y_Zfdzrudetr8_kjy-pdxGM2jsTyaSFm84d5_PI6FVu_056Xyou1a6qy-_Xf5C8punIQ</recordid><startdate>19910201</startdate><enddate>19910201</enddate><creator>Oliver, Douglas W</creator><creator>Dekker, Theodor G</creator><creator>Snyckers, Friedrich O</creator><creator>Fourie, Theunis G</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></search><sort><creationdate>19910201</creationdate><title>Synthesis and biological activity of D3-trishomocubyl-4-amines</title><author>Oliver, Douglas W ; Dekker, Theodor G ; Snyckers, Friedrich O ; Fourie, Theunis G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a354t-20310bcc653d81e82d1e378aeac48f653e1122d00f9853b262e8e0c42f4cd0cd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1991</creationdate><topic>Animals</topic><topic>Antiparkinson Agents - chemical synthesis</topic><topic>Antiparkinson Agents - therapeutic use</topic><topic>Antiparkinson Agents - toxicity</topic><topic>Bridged-Ring Compounds - chemical synthesis</topic><topic>Bridged-Ring Compounds - therapeutic use</topic><topic>Bridged-Ring Compounds - toxicity</topic><topic>Catalepsy - drug therapy</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Male</topic><topic>Mice</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Oliver, Douglas W</creatorcontrib><creatorcontrib>Dekker, Theodor G</creatorcontrib><creatorcontrib>Snyckers, Friedrich O</creatorcontrib><creatorcontrib>Fourie, Theunis G</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><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Oliver, Douglas W</au><au>Dekker, Theodor G</au><au>Snyckers, Friedrich O</au><au>Fourie, Theunis G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological activity of D3-trishomocubyl-4-amines</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1991-02-01</date><risdate>1991</risdate><volume>34</volume><issue>2</issue><spage>851</spage><epage>854</epage><pages>851-854</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>The D3-trishomocubyl system was prepared from tertiary pentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-ols 5 in one step by using a modified Ritter reaction yielding only one of the possible two geometrical isomers of 4-amino-3-alkyl (or aryl)-D3-trishomocubane (8). Promising antagonism of reserpine-induced catalepsy was exhibited by these compounds which compared favorable with that of amantadine. Weak to mild anticholinergic properties were observed during the reduction of oxotremorine induced tremor and salivation procedure. Acute toxicities similar to that of amantadine were observed for some of these compounds. D3-Trishomocubyl-4-amines appeared as a promising new class of anti-Parkinson agents.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>1995908</pmid><doi>10.1021/jm00106a053</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1991-02, Vol.34 (2), p.851-854 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Animals Antiparkinson Agents - chemical synthesis Antiparkinson Agents - therapeutic use Antiparkinson Agents - toxicity Bridged-Ring Compounds - chemical synthesis Bridged-Ring Compounds - therapeutic use Bridged-Ring Compounds - toxicity Catalepsy - drug therapy Chemical Phenomena Chemistry Male Mice Stereoisomerism Structure-Activity Relationship |
| title | Synthesis and biological activity of D3-trishomocubyl-4-amines |
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