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

David Burdick; Russell DeOrazio; Peter Guzzo; Alicia Habershaw; Mark Helle; Bernard Paul; Mark Wolf

doi:10.1016/j.bmcl.2009.12.092

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

Bioorg Med Chem Lett. 2010 Feb 15;20(4):1424-6. doi: 10.1016/j.bmcl.2009.12.092. Epub 2010 Jan 4.

Authors

David Burdick¹, Russell DeOrazio, Peter Guzzo, Alicia Habershaw, Mark Helle, Bernard Paul, Mark Wolf

Affiliation

¹ AMRI, 26 Corporate Circle, PO Box 15098, Albany, NY 12212-5098, USA.

PMID: 20079638
DOI: 10.1016/j.bmcl.2009.12.092

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.

MeSH terms

Animals
Catalysis
Dronabinol / chemical synthesis*
Dronabinol / chemistry
Dronabinol / pharmacology
Molecular Structure
Palladium / chemistry*
Receptors, Cannabinoid / classification
Receptors, Cannabinoid / drug effects*
Structure-Activity Relationship

Substances

Receptors, Cannabinoid
Palladium
Dronabinol