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
Hauptverfasser:	Dixon, Darryl D, Sethumadhavan, Divakaramenon, Benneche, Tore, Banaag, April R, Tius, Marcus A, Thakur, Ganesh A, Bowman, Anna, Wood, JodiAnne T, Makriyannis, Alexandros
Format:	Artikel
Sprache:	eng
Schlagworte:	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
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Beschreibung
Zusammenfassung:	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.
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm100390h