title: Synthesis and structure-activity relationship of substitutions at the C-1 position of Delta9-tetrahydrocannabinol.
abstract: 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.
authors.affiliation: AMRI, 26 Corporate Circle, PO Box 15098, Albany, NY 12212-5098, USA.
authors.forename: David
authors.initials: D
authors.lastname: Burdick
authors.forename: Russell
authors.initials: R
authors.lastname: DeOrazio
authors.forename: Peter
authors.initials: P
authors.lastname: Guzzo
authors.forename: Alicia
authors.initials: A
authors.lastname: Habershaw
authors.forename: Mark
authors.initials: M
authors.lastname: Helle
authors.forename: Bernard
authors.initials: B
authors.lastname: Paul
authors.forename: Mark
authors.initials: M
authors.lastname: Wolf
mesh_terms: 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
chemical_list: D043882:Receptors, Cannabinoid; D010165:Palladium; D013759:Dronabinol