Synthesis and structure-activity relationship of substitutions at the C-1 position of Delta9-tetrahydrocannabinol.
A novel series of Delta9-tetrahydrocannabinol (Delta9-THC) analogues were synthesized to determine their potential as cannabinoid receptor modulators. Chemistry focused on conversion of the phenol of Delta9-THC to other functionality through palladium catalyzed reactions with an intermediate triflate 2. Two analogues with sub 100 nM affinity for the CB1 and CB2 receptors were identified.
Burdick
David
D
AMRI, 26 Corporate Circle, PO Box 15098, Albany, NY 12212-5098, USA.
DeOrazio
Russell
R
Guzzo
Peter
P
Habershaw
Alicia
A
Helle
Mark
M
Paul
Bernard
B
Wolf
Mark
M
D000818:Animals; D002384:Catalysis; D013759:Dronabinol / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D043882:Receptors, Cannabinoid / Q000145:classification / Q000187:drug effects*; D013329:Structure-Activity Relationship
D043882:Receptors, Cannabinoid; D010165:Palladium; D013759:Dronabinol