Cyclic hydroxyamidines as amide isosteres: discovery of oxadiazolines and oxadiazines as potent and highly efficacious γ-secretase modulators in vivo

J Med Chem. 2012 Jan 12;55(1):489-502. doi: 10.1021/jm201407j. Epub 2011 Dec 8.

Abstract

Cyclic hydroxyamidines were designed and validated as isosteric replacements of the amide functionality. Compounds with these structural motifs were found to be metabolically stable and to possess highly desirable pharmacokinetic profiles. These designs were applied in the identification of γ-secretase modulators leading to highly efficacious agents for reduction of central nervous system Aβ(42) in various animal models.

MeSH terms

  • Amidines / chemical synthesis*
  • Amidines / pharmacokinetics
  • Amidines / pharmacology
  • Amyloid Precursor Protein Secretases / metabolism*
  • Amyloid beta-Peptides / metabolism
  • Animals
  • Brain / metabolism
  • Dogs
  • HEK293 Cells
  • Humans
  • Macaca fascicularis
  • Male
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / pharmacokinetics
  • Oxadiazoles / pharmacology
  • Oxazines / chemical synthesis*
  • Oxazines / pharmacokinetics
  • Oxazines / pharmacology
  • Peptide Fragments / metabolism
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Amidines
  • Amyloid beta-Peptides
  • Oxadiazoles
  • Oxazines
  • Peptide Fragments
  • amyloid beta-protein (1-40)
  • amyloid beta-protein (1-42)
  • Amyloid Precursor Protein Secretases