Heteroadamantyl Cannabinoids
The aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have synthesized a series of analogues in which the C3 position is substituted either directly or through a one-carbon atom linker with an adamantylamine or with an oxa- or...
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| Veröffentlicht in: | Journal of medicinal chemistry 2010-08, Vol.53 (15), p.5656-5666 |
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| container_end_page | 5666 |
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| container_issue | 15 |
| container_start_page | 5656 |
| container_title | Journal of medicinal chemistry |
| container_volume | 53 |
| creator | Dixon, Darryl D Sethumadhavan, Divakaramenon Benneche, Tore Banaag, April R Tius, Marcus A Thakur, Ganesh A Bowman, Anna Wood, JodiAnne T Makriyannis, Alexandros |
| description | The aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have synthesized a series of analogues in which the C3 position is substituted either directly or through a one-carbon atom linker with an adamantylamine or with an oxa- or an oxazaadamantane. The oxaadamantane pharmacophore in analogue 16 showed the best binding profile for both receptors. |
| doi_str_mv | 10.1021/jm100390h |
| format | Article |
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We have synthesized a series of analogues in which the C3 position is substituted either directly or through a one-carbon atom linker with an adamantylamine or with an oxa- or an oxazaadamantane. The oxaadamantane pharmacophore in analogue 16 showed the best binding profile for both receptors.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm100390h</identifier><identifier>PMID: 20593789</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Adamantane - analogs & derivatives ; Adamantane - chemical synthesis ; Adamantane - pharmacology ; Animals ; Brain - metabolism ; Cannabinoids - chemical synthesis ; Cannabinoids - pharmacology ; Cell Line ; Humans ; In Vitro Techniques ; Mice ; Models, Molecular ; Radioligand Assay ; Rats ; Receptor, Cannabinoid, CB1 - metabolism ; Receptor, Cannabinoid, CB2 - metabolism ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2010-08, Vol.53 (15), p.5656-5666</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>2010 American Chemical Society 2010</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a404t-25d30577ed4ffead81948a1b880cef994eb2d9ee2f989bc86f715d52fa0a3cd83</citedby><cites>FETCH-LOGICAL-a404t-25d30577ed4ffead81948a1b880cef994eb2d9ee2f989bc86f715d52fa0a3cd83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm100390h$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm100390h$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2764,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20593789$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dixon, Darryl D</creatorcontrib><creatorcontrib>Sethumadhavan, Divakaramenon</creatorcontrib><creatorcontrib>Benneche, Tore</creatorcontrib><creatorcontrib>Banaag, April R</creatorcontrib><creatorcontrib>Tius, Marcus A</creatorcontrib><creatorcontrib>Thakur, Ganesh A</creatorcontrib><creatorcontrib>Bowman, Anna</creatorcontrib><creatorcontrib>Wood, JodiAnne T</creatorcontrib><creatorcontrib>Makriyannis, Alexandros</creatorcontrib><title>Heteroadamantyl Cannabinoids</title><title>Journal of medicinal chemistry</title><addtitle>J. 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| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 2010-08, Vol.53 (15), p.5656-5666 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3699191 |
| source | MEDLINE; ACS Publications |
| subjects | Adamantane - analogs & derivatives Adamantane - chemical synthesis Adamantane - pharmacology Animals Brain - metabolism Cannabinoids - chemical synthesis Cannabinoids - pharmacology Cell Line Humans In Vitro Techniques Mice Models, Molecular Radioligand Assay Rats Receptor, Cannabinoid, CB1 - metabolism Receptor, Cannabinoid, CB2 - metabolism Structure-Activity Relationship |
| title | Heteroadamantyl Cannabinoids |
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