180989-30-4

Upstream product

• 180989-35-9 1-(3,5-dimethoxyphenyl)-1-heptyne 
• 180989-36-0 1-(3,5-dihydroxyphenyl)-1-heptyne 
• 171290-52-1 1-Ethynyl-3,5-dimethoxy-benzene 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 39151-19-4 1-(3,5-dimethoxyphenyl)ethan-1-one 
• 110-53-2 1-Bromopentane 

Relevant academic research and scientific papers

Unsaturated side chain β-11-hydroxyhexahydrocannabinol analogs

The cannabinoid side chain is a key pharmacophore in the interaction of cannabinoids with their receptors (CB1 and CB2). To study the stereochemical requirements of the side chain, we synthesized a series of cannabinoids in which rotation around the C1'-C2' bond is blocked. The key steps in the synthesis were the cuprate addition of a substituted resorcinol to (+)- apoverbenone, the TMSOTf-mediated formation of the dihydropyran ring, and the stereospecific introduction of the β-11-hydroxymethyl group. All the analogs tested showed nanomolar affinity for the receptors, the cis-hept-1-ene side chain having the highest affinity for CB1 (K(i) = 0.89 nM) and showing the widest separation between CB1 and CB2 affinities. The parent n-heptyl-β-11- hydroxyhexahydrocannabinol was the least potent binding to CB1 (K(i) = 8.9 nM) and had the lowest selectivity between CB1 and CB2.