The natural product resveratrol has received much attention in the past decade for its ability to prevent cancer, increase longevity, and reduce incidences of heart disease in mice. The search for understanding resveratrol's mechanism of action has lead to the discovery of several targets; one in particular, quinone reductase II, is the focus of this paper. This enzyme converts quinone to hydroquinone through reduction and oxidation of the cofactor FAD. While little else is understood about the biological role of QR2, it is becoming more widely accepted that QR2 inhibition might contribute to resveratrol's medicinal properties. As resveratrol is rapidly metabolized by sulfation and glucuronidation, large doses of resveratrol are required to produce noticeable effects in mice, necessitating the design of more stable and potent analogs. In this presentation, we showcase the synthesis of novel resveratrol analogues, azo-resveratrols, that can generally be synthesized using a one-pot, one-step, green reaction. The efficacy of many of these analogs is reported to be similar to resveratrol and more potent than some other known inhibitors of QR2. Finally, the binding of these analogs has been analyzed using X-ray crystallographic data from five lead structures, which should allow the design of more potent inhibitors in the near future.

Novel azo-resveratrol analogs as inhibitors of quinone reductase II

247th National Meeting (2014)

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