1070295-92-9Relevant academic research and scientific papers
Synthesis and characterization of 2-substituted bornane pharmacophores for novel cannabinergic ligands
Duclos Jr., Richard I.,Lu, Dai,Guo, Jianxin,Makriyannis, Alexandros
, p. 5587 - 5589 (2008)
Analogously to the fenchyl and adamantyl groups, the bornyl and epimeric isobornyl groups are compact lipophilic substituents that can be incorporated into drug design to improve pharmacological or physicochemical properties. Methods are reported for the
Bornyl- and isobornyl-Δ8-tetrahydrocannabinols: A novel class of cannabinergic ligands
Lu, Dai,Guo, Jianxin,Duclos Jr., Richard I.,Bowman, Anna L.,Makriyannis, Alexandros
body text, p. 6393 - 6399 (2009/10/17)
Structure-activity relationship studies of classical cannabinoid analogues have established that the C3 aliphatic side chain plays a pivotal role in determining cannabinergic potency. In earlier work, we provided evidence for the presence of subsites within the CB1 and CB2 cannabinoid receptor binding domains that can accommodate bulky conformationally defined substituents at the C3 alkyl side chain pharmacophore of classical cannabinoids. We have now extended this work with the synthesis of a series of Δ8-THC analogues in which bornyl substituents are introduced at the C3 position. Our results indicate that, for optimal interactions with both CB1 and CB2 receptors, the bornyl substituents need to be within close proximity of the tricyclic core of Δ8-THC and that the conformational space occupied by the C3 substituents influences CB1/CB2 receptor subtype selectivity.
