Natural cannabinoids: Templates for drug discovery

Recent studies have elucidated the biosynthetic pathway of cannabinoids and have highlighted the preference for a C-3 n-pentyl side chain in the most prominently represented cannabinoids from Cannabis sativa and their medicinally important decarboxylation products. The corresponding C-3 n-propyl sid...

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Bibliographic Details
Published in:Life sciences (1973) 2005-12, Vol.78 (5), p.454-466
Main Authors: Thakur, Ganesh A., Duclos, Richard I., Makriyannis, Alexandros
Format: Article
Language:English
Subjects:
Anandamide
Animals
Biosynthesis
Cannabinoid Receptor Modulators - biosynthesis
Cannabinoid Receptor Modulators - chemistry
Cannabinoid Receptor Modulators - pharmacology
Cannabinoids - biosynthesis
Cannabinoids - chemistry
Cannabinoids - pharmacology
Endocannabinoids
Humans
Molecular Conformation
Pharmacology
Side chain SAR
Structure-Activity Relationship
Δ 9-Tetrahydrocannabinol
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Summary:Recent studies have elucidated the biosynthetic pathway of cannabinoids and have highlighted the preference for a C-3 n-pentyl side chain in the most prominently represented cannabinoids from Cannabis sativa and their medicinally important decarboxylation products. The corresponding C-3 n-propyl side chain containing cannabinoids are also found, although in lesser quantities. Structure–activity relationship (SAR) studies performed on Δ 9-tetrahydrocannabinol (Δ 9-THC), the key psychoactive ingredient of Cannabis, and its synthetic analogues have identified the C-3 side chain as the key pharmacophore for ligand affinity and selectivity for the known cannabinoid receptors and for pharmacological potency. Interestingly, the terminal n-pentyl saturated hydrocarbon side chain of endocannabinoids also plays a corresponding crucial role in conferring similar properties. This review briefly summarizes the biosynthesis of cannabinoids and endocannabinoids and focuses on their side chain SAR.
ISSN:0024-3205
1879-0631
DOI:10.1016/j.lfs.2005.09.014