Identification, synthesis and SAR of amino substituted pyrido[3,2b]pyrazinones as potent and selective PDE5 inhibitors

Bioorg Med Chem Lett. 2009 Aug 1;19(15):4088-91. doi: 10.1016/j.bmcl.2009.06.012. Epub 2009 Jun 6.

Abstract

A new class of potent and selective PDE5 inhibitors is disclosed. Guided by X-ray crystallographic data, optimization of an HTS lead led to the discovery of a series of 2-aryl, (N8)-alkyl substituted-6-aminosubstituted pyrido[3,2b]pyrazinones which show potent inhibition of the PDE5 enzyme. Synthetic details and some structure-activity relationships are also presented.

MeSH terms

  • 3',5'-Cyclic-GMP Phosphodiesterases
  • Animals
  • Catalytic Domain
  • Chemistry, Pharmaceutical / methods
  • Crystallography, X-Ray / methods
  • Cyclic Nucleotide Phosphodiesterases, Type 5 / chemistry*
  • Cyclic Nucleotide Phosphodiesterases, Type 6 / antagonists & inhibitors
  • Cyclic Nucleotide Phosphodiesterases, Type 6 / chemistry
  • Drug Design
  • Humans
  • Hydrogen-Ion Concentration
  • Inhibitory Concentration 50
  • Phosphodiesterase 5 Inhibitors*
  • Phosphodiesterase Inhibitors / chemical synthesis
  • Phosphodiesterase Inhibitors / pharmacology
  • Phosphoric Diester Hydrolases / chemistry
  • Protein Structure, Tertiary
  • Pyrazines / chemical synthesis*
  • Pyrazines / pharmacology
  • Rats
  • Structure-Activity Relationship

Substances

  • Phosphodiesterase 5 Inhibitors
  • Phosphodiesterase Inhibitors
  • Pyrazines
  • Phosphoric Diester Hydrolases
  • 3',5'-Cyclic-GMP Phosphodiesterases
  • Cyclic Nucleotide Phosphodiesterases, Type 5
  • Cyclic Nucleotide Phosphodiesterases, Type 6
  • PDE11A protein, human