Novel 1',1'-chain substituted Delta(8)-tetrahydrocannabinols.
1',1'-Cyclopropyl side chain substituents enhance the affinities of Delta(8)-tetrahydrocannabinol and respective cannabidiol analogues for the CB1 and CB2 cannabinoid receptors. The results support the hypothesis for a subsite within CB1 and CB2 binding domain at the level of the benzylic side chain carbon in the tetrahydrocannabinol and cannabidiol series. Efficient procedures for the synthesis of 1',1'-cyclopropyl analogues are described.
Papahatjis
Demetris P
DP
Institute of Organic and Pharmaceutical Chemistry, National Hellenic Research Foundation, 48 Vass. Constantinou, Athens 116-35, Greece.
Nikas
Spyros P
SP
Andreou
Thanos
T
Makriyannis
Alexandros
A
D018712:Analgesics, Non-Narcotic / Q000138:chemical synthesis* / Q000494:pharmacology; D001665:Binding Sites; D013759:Dronabinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008024:Ligands; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug / Q000378:metabolism; D013329:Structure-Activity Relationship
D018712:Analgesics, Non-Narcotic; D008024:Ligands; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug; D013759:Dronabinol