4-Aryl-2-hydroxytetronimides, like the related 4-aryl-2-hydroxytetronic acids, are antioxidants that have potent reactive oxygen species (ROS) quenching activities.  However, despite the synthesis and biological evaluation of many 4-aryl-2-hydroxytetronic acids, biological characterization of 4-aryl-2-hydroxytetronimides have been neglected.  In the development of modular pharmaceutical agents, 2-hydroxytetronimides have greater theoretical potential relative to 2-hydroxytetronic acids, because 2-hydroxytetronic acids can only be incorporated in terminal modules, whereas 2-hydroxytetronimides can be incorporated into both terminal and internal modules due to the ability to attach functional groups to the hydroxytetronimide nitrogen.  Here, we report the synthesis of 4(fluorophenyl)-2-hydroxytetronimides, and for the first time describe the anticonvulsant activity of these antioxidants.  Despite the modest anticonvulsant activity of the 4(fluorophenyl)-2-hydroxytetronimides described, these molecules may be elaborated into more complex, potent antiepileptogenic agents.

Synthesis and anticonvulsant activity of 4-aryl-2-hydroxytetronimides

243rd National Meeting (2012)

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