Synthesis and Evaluation of Bicyclic Hydroxypyridones as Inhibitors of Catechol O-Methyltransferase

Glen Ernst, Daniel Akuma, Vinh Au, Ingrid P. Buchler, Spencer Byers, Gregory V. Carr, Sabine Defays, Pablo De León, Thierry Demaude, Michael Depasquale, Véronique Durieu, Yifang Huang, Emilie Jigorel, Martha Kimos, Anna Kolobova, Florian Montel, Florence Moureau, Michael Poslusney, Dominique Swinnen, Marie Christine VandergetenNathalie Van Houtvin, Huijun Wei, Noelle White, Martyn Wood, James C. Barrow

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

A series of bicyclic pyridones were identified as potent inhibitors of catechol O-methyltransferase (COMT). Substituted benzyl groups attached to the basic nitrogen of the core scaffold gave the most potent inhibitors within this series. Rat pharmacokinetic studies showed medium to high levels of clearance for this series, but with high free fraction due to remarkably low levels of protein and tissue binding. In rat biomarker studies, levels of unbound drug exposure are seen in the brain, which exceed their respective IC50s, leading to changes in the levels of dopamine metabolites in a manner consistent with COMT inhibition.

Original languageEnglish (US)
Pages (from-to)1573-1578
Number of pages6
JournalACS Medicinal Chemistry Letters
Volume10
Issue number11
DOIs
StatePublished - Nov 14 2019

Keywords

  • Catechol O-methyl transferase
  • catechol mimic
  • dopamine metabolism
  • enzyme inhibitors

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis and Evaluation of Bicyclic Hydroxypyridones as Inhibitors of Catechol O-Methyltransferase'. Together they form a unique fingerprint.

Cite this