Synthesis and biological evaluation of D-amino acid oxidase inhibitors

J Med Chem. 2008 Jun 26;51(12):3357-9. doi: 10.1021/jm800200u. Epub 2008 May 29.

Abstract

D-amino acid oxidase (DAAO) catalyzes the oxidation of D-amino acids including d-serine, a full agonist at the glycine site of the NMDA receptor. A series of benzo[ d]isoxazol-3-ol derivatives were synthesized and evaluated as DAAO inhibitors. Among them, 5-chloro-benzo[ d]isoxazol-3-ol (CBIO) potently inhibited DAAO with an IC50 in the submicromolar range. Oral administration of CBIO in conjunction with d-serine enhanced the plasma and brain levels of d-serine in rats compared to the oral administration of d-serine alone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Animals
  • Benzoxazoles / chemical synthesis*
  • Benzoxazoles / chemistry
  • Benzoxazoles / pharmacology
  • Brain / metabolism
  • D-Amino-Acid Oxidase / antagonists & inhibitors*
  • Drug Synergism
  • Isoxazoles / chemical synthesis*
  • Isoxazoles / chemistry
  • Isoxazoles / pharmacology
  • Male
  • Rats
  • Rats, Sprague-Dawley
  • Serine / administration & dosage
  • Serine / metabolism
  • Serine / pharmacology
  • Structure-Activity Relationship

Substances

  • 5-chlorobenzo(d)isoxazol-3-ol
  • Benzoxazoles
  • Isoxazoles
  • Serine
  • D-Amino-Acid Oxidase