Synthesis of kojic acid derivatives as secondary binding site probes of D-amino acid oxidase

Bioorg Med Chem Lett. 2013 Jul 1;23(13):3910-3. doi: 10.1016/j.bmcl.2013.04.062. Epub 2013 May 1.

Abstract

A series of kojic acid (5-hydroxy-2-hydroxymethyl-4H-pyran-4-one) derivatives were synthesized and tested for their ability to inhibit D-amino acid oxidase (DAAO). Various substituents were incorporated into kojic acid at its 2-hydroxymethyl group. These analogs serve as useful molecular probes to explore the secondary binding site, which can be exploited in designing more potent DAAO inhibitors.

Publication types

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

MeSH terms

  • Binding Sites / drug effects
  • D-Amino-Acid Oxidase / antagonists & inhibitors*
  • D-Amino-Acid Oxidase / metabolism
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Models, Molecular
  • Molecular Probes / chemical synthesis
  • Molecular Probes / chemistry
  • Molecular Probes / pharmacology*
  • Molecular Structure
  • Pyrones / chemical synthesis
  • Pyrones / chemistry
  • Pyrones / pharmacology*
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Molecular Probes
  • Pyrones
  • kojic acid
  • D-Amino-Acid Oxidase