Synthesis, biological evaluation, and NMR studies of 3-fluorinated derivatives of 3′,4′,5′-trihydroxyflavone and 3′,4′,5′-trimethoxyflavone

Abstract

Flavones are valuable scaffolds in medicinal chemistry, especially as they display activity as antioxidants and neuroprotective agents. The need to incorporate a fluorine atom on flavones has driven much of the recent synthetic work in this area. We now report a route for the production of 3-fluorinated derivatives of 3′,4',5'-trihydroxyflavone and 3′,4′,5′-trimethoxyflavone. Biological evaluation of these agents, along with their non-fluorinated counterparts, demonstrate that antioxidant activity may be enhanced whereas neuroprotective activity is conserved. Also, the 3-fluoro-3′,4',5'-trihydroxyflavone can act as an NMR probe to detect structural changes during its action as a radical scavenger.