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 triflat...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2010-02, Vol.20 (4), p.1424-1426
Hauptverfasser:	Burdick, David, DeOrazio, Russell, Guzzo, Peter, Habershaw, Alicia, Helle, Mark, Paul, Bernard, Wolf, Mark
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Catalysis Dronabinol - chemical synthesis Dronabinol - chemistry Dronabinol - pharmacology Molecular Structure Palladium - chemistry Receptors, Cannabinoid - classification Receptors, Cannabinoid - drug effects Structure-Activity Relationship
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Zusammenfassung:	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.
ISSN:	1464-3405
DOI:	10.1016/j.bmcl.2009.12.092