Pawhuskin A (1 ), isolated from the purple prairie clover by Belofsky and co-workers, is a rare example of a non-nitrogenous natural product that binds selectively to an opioid receptor as a competitive antagonist. Since the pawhuskins were identified, we have synthesized two of the natural products along with a number of pawhuskin analogues intended to elucidate the novel pharmacophore. Compounds which are very similar structurally to ones with weak to moderate binding affinity as competitive antagonists may bind with equal or greater affinity than synthetic pawhuskin A to a negative allosteric site(s). The chemical syntheses of several new pawhuskin analogues will be presented, in addition to on-going efforts to discover the various opioid receptor interaction(s) through further compound design and synthesis.

New analogs of pawhuskin A

246th National Meeting (2013)

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