Synthesis and radical trapping of novel heterocyclic aromatic nitrones

CHED 469

Chris W Beier, beie3@fsuimail.ferris.edu1, Michael A LaFontaine, lafontam@ferris.edu1, and Folami T. Ladipo, fladip0@uky.edu2. (1) Department of Pharmaceutical Sciences, Ferris State University, 220 Ferris Ave., Big Rapids, MI 49307, (2) Department of Chemistry, University of Kentucky, Lexington, KY 40506
Free radical spin-traps are diamagnetic species that react with reactive free radicals to form stable paramagnetic species detectable by Electron Paramagnetic Resonance (EPR). As antioxidants, spin-traps are being investigated as possible therapeutic agents to protect against neurological diseases. The key step in the synthesis of most spin-traps is the formation of the nitrone moiety. Usually, these are one-pot, zinc-catalyzed reactions that are easily performed from commercially available starting materials and are directly characterized. Though aromatic nitrones are studied in the literature, heterocyclic aromatic nitrones have not been. We synthesized several novel heterocyclic aromatic nitrones and studied their free-radical trapping capabilities using fluorescence assays to determine the effect of heterocycles.