Event Title
Synthesis of Novel Dibenzofuran Analogues
Faculty Sponsor
Mark L.Trudell
College(s)
College of Sciences
Submission Type
Oral Presentation
Description
Among known cannabinoid agonists several compounds have been reported to exhibit low efficacy agonist profiles in vitro and in vivo. A structurally unique cannabinoid agonist is the diaryl ether BAY59-3704. This compound was significantly less efficacious than the full cannabinoid agonists and hence has been designated as partial agonists. It is noteworthy that BAY 59-3074 exhibited no abuse potential and did not produce withdrawal behavioral effects when daily doses were stopped after two weeks. Therefore BAY59-3704 is an attractive target to explore the structure-activity relationships for the potential development of a therapeutic target for cannabis addiction. / / This presentation will describe the studies associated with the optimization of the palladium-catalyzed oxidative ring closure reaction for the synthesis of dibenzofuran analogues from substituted diaryl ethers. These compounds are viewed as rigid analogues of BAY 59-3704 and will provide useful information about molecular interactions at cannabinoid receptors. In addition the scope and any limitations of the palladium-catalyzed oxidative ring closure reaction as it relates to the synthesis of the target dibenzofuran analogues is also presented. / /
Synthesis of Novel Dibenzofuran Analogues
Among known cannabinoid agonists several compounds have been reported to exhibit low efficacy agonist profiles in vitro and in vivo. A structurally unique cannabinoid agonist is the diaryl ether BAY59-3704. This compound was significantly less efficacious than the full cannabinoid agonists and hence has been designated as partial agonists. It is noteworthy that BAY 59-3074 exhibited no abuse potential and did not produce withdrawal behavioral effects when daily doses were stopped after two weeks. Therefore BAY59-3704 is an attractive target to explore the structure-activity relationships for the potential development of a therapeutic target for cannabis addiction. / / This presentation will describe the studies associated with the optimization of the palladium-catalyzed oxidative ring closure reaction for the synthesis of dibenzofuran analogues from substituted diaryl ethers. These compounds are viewed as rigid analogues of BAY 59-3704 and will provide useful information about molecular interactions at cannabinoid receptors. In addition the scope and any limitations of the palladium-catalyzed oxidative ring closure reaction as it relates to the synthesis of the target dibenzofuran analogues is also presented. / /
Comments
2nd place, Oral Presentation, College of Sciences