A class of novel compounds consisting of a diaryl ether scaffold has exhibited affinity for the cannabinoid CB1 receptor.  In order to understand structure-activity relationships (SARs) of these compounds, several synthetic methods have been developed to produce general diaryl ether scaffolds that could be further modified to yield potentially therapeutic cannabinoids.  An early result of these experiments was the discovery of AMS167, a novel high-affinity (Ki = 1.2 nM) CB1 receptor neutral antagonist.  Modified versions of this lead compound have been synthesized and we are currently awaiting bioassay results. Additional novel diaryl ethers have been proposed (and synthesized), though pending bioassay results will have the greatest influence on the future course of this project. Future goals of this project involve further manipulation of the diaryl ether scaffold, including fusing the structures into planar dibenzofuran analogs and incorporating other aromatic heterocycles, such as indole, into the scaffold.

Synthesis and biological evaluation of diaryl ether cannabinoids

245th National Meeting (2013)

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