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 an oxazaadamantane. The oxaadamantane pharmacophore in analogue 16 showed the best binding profile for both receptors.
Dixon
Darryl D
DD
Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822, USA.
Sethumadhavan
Divakaramenon
D
Benneche
Tore
T
Banaag
April R
AR
Tius
Marcus A
MA
Thakur
Ganesh A
GA
Bowman
Anna
A
Wood
Jodianne T
JT
Makriyannis
Alexandros
A
D000218:Adamantane / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001921:Brain / Q000378:metabolism; D002186:Cannabinoids / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D006801:Humans; D066298:In Vitro Techniques; D051379:Mice; D008958:Models, Molecular; D011869:Radioligand Assay; D051381:Rats; D043884:Receptor, Cannabinoid, CB1 / Q000378:metabolism*; D043885:Receptor, Cannabinoid, CB2 / Q000378:metabolism*; D013329:Structure-Activity Relationship
D002186:Cannabinoids; D043884:Receptor, Cannabinoid, CB1; D043885:Receptor, Cannabinoid, CB2; D000218:Adamantane