Lipophilic phenolic antioxidants: Correlation between antioxidant profile, partition coefficients and redox properties

Lipophilic compounds structurally based on caffeic, hydrocaffeic, ferulic and hydroferulic acids were synthesized. Subsequently, their antioxidant activity was evaluated as well as their partition coefficients and redox potentials. The structure–property–activity relationship (SPAR) results revealed the existence of a clear correlation between the redox potentials and the antioxidant activity. In addition, some compounds showed a proper lipophilicity to cross the blood–brain barrier. Their predicted ADME properties are also in accordance with the general requirements for potential CNS drugs. Accordingly, one can propose these phenolic compounds as potential antioxidants for tackling the oxidative status linked to the neurodegenerative processes.

Lipophilic derivatives of cinnamic and hydrocinnamic acids have been prepared. The structure–property–activity relationship data revealed a correlation between the redox potentials and the antioxidant activity. Some compounds showed to have a proper lipophilicity to cross BBB.Figure optionsDownload as PowerPoint slide