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

Article Details

Citation

Burdick D, DeOrazio R, Guzzo P, Habershaw A, Helle M, Paul B, Wolf M

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.

PubMed ID
20079638 [ View in PubMed
]
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.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
DronabinolCannabinoid receptor 1Ki (nM)40N/AN/ADetails
DronabinolCannabinoid receptor 2Ki (nM)36N/AN/ADetails