G-protein coupled receptors (GPCRs) are the largest and most diverse class of membrane receptors in the human body. GPCRs are pharmacologically relevant, with 34% of all drugs affecting at least one GPCR. The sigma-1 receptor is a GPCR that recent research has implicated as a target to potentially treat addiction, breast and colon cancer, and Alzheimer’s disease, which makes it an exciting target. Previous work in the Topczewski group found that a class of small molecules are potent ligands for the sigma-1 receptor. The synthesis of these novel substituted chromanes was conducted via an allylic azide intermediate, which was further derivatized. These heterocycles contain the phenethylamine motif, which is common among many endogenous and exogenous GPCR ligands. In this study, we separated the chromane core into its constituent enantiomers and then functionalized the enantipure products, producing 36 novel compounds (18 pairs of enantiomers). These compounds have been submitted for assay against the human sigma-1 receptor.

Synthesis of GPCR and sigma-1 receptor ligands using allylic azides

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.