Journal
CHEMMEDCHEM
Volume 15, Issue 9, Pages 728-732Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cmdc.202000025
Keywords
cannabinoids; cannabinol; atropisomerism; axial chirality; total synthesis
Categories
Funding
- NIGMS NIH HHS [R35 GM137893] Funding Source: Medline
- NIH HHS [S10 OD021758] Funding Source: Medline
Ask authors/readers for more resources
Phytocannabinoids (and synthetic analogs thereof) are gaining significant attention as promising leads in modern medicine. Considering this, new directions for the design of phytocannabinoid-inspired molecules is of immediate interest. In this regard, we have hypothesized that axially-chiral-cannabinols (ax-CBNs), unnatural and unknown isomers of cannabinol (CBN) may be valuable scaffolds for cannabinoid-inspired drug discovery. There are two main factors directing our interest to these scaffolds: (a) ax-CBNs would have ground-state three-dimensionality; ligand-receptor interactions can be more significant with complimentary 3D-topology, and (b) ax-CBNs at their core structure are biaryl molecules, generally attractive platforms for pharmaceutical development due to their ease of functionalization and stability. Herein we report a synthesis of ax-CBNs, examine physical properties experimentally and computationally, and perform a comparative analysis of ax-CBN and THC in mice behavioral studies.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available