Analysis of the inhibition of mammalian carboxylesterases by novel fluorobenzoins and fluorobenzils

We have synthesized and assessed the ability of symmetrical fluorobenzoins and fluorobenzils to inhibit mammalian carboxylesterases (CE). The majority of the latter were excellent inhibitors of CEs however unexpectedly, the fluorobenzoins were very good enzyme inhibitors. Positive correlations were seen with the charge on the hydroxyl carbon atom, the carbonyl oxygen, and the Hammett constants for the derived Ki values with the fluorobenzoins.

The inhibition of mammalian carboxylesterases by fluorobenzoins and fluorobenzils has been evaluated. These studies demonstrated that the electronic charge on the central atoms impacts the biological activity of these molecules.Figure optionsDownload as PowerPoint slide