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  • Synthesis and structure-activity relationship of substitutions at the C-1 position of Delta9-tetrahydrocannabinol.

Synthesis and structure-activity relationship of substitutions at the C-1 position of Delta9-tetrahydrocannabinol.

Bioorganic & medicinal chemistry letters (2010-01-19)
David Burdick, Russell DeOrazio, Peter Guzzo, Alicia Habershaw, Mark Helle, Bernard Paul, Mark Wolf
PMID20079638
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.