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

Bioorg Med Chem. 2007 Jun 1;15(11):3801-17. doi: 10.1016/j.bmc.2007.03.012. Epub 2007 Mar 12.

Abstract

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 K(i) values with the fluorobenzoins.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoin / analogs & derivatives*
  • Carboxylic Ester Hydrolases / antagonists & inhibitors*
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Hydrocarbons, Fluorinated / chemistry*
  • Hydrocarbons, Fluorinated / pharmacology*
  • Phenylglyoxal / analogs & derivatives*
  • Phenylglyoxal / chemistry
  • Quantitative Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Hydrocarbons, Fluorinated
  • Carboxylic Ester Hydrolases
  • Benzoin
  • Phenylglyoxal
  • benzil