Synthesis and evaluation of succinoyl-caprolactam gamma-secretase inhibitors

Bioorg Med Chem Lett. 2006 May 1;16(9):2357-63. doi: 10.1016/j.bmcl.2006.01.055. Epub 2006 Feb 10.

Abstract

The synthesis, evaluation, and structure-activity relationships of a series of succinoyl lactam inhibitors of the Alzheimer's disease gamma-secretase are described. Beginning with a screening hit with broad proteinase activity, optimization provided compounds with both high selectivity for inhibition of gamma-secretase and high potency in cellular assays of A beta reduction. The SAR and early in vivo properties of this series of inhibitors will be presented.

MeSH terms

  • Alzheimer Disease / drug therapy
  • Alzheimer Disease / enzymology
  • Amyloid Precursor Protein Secretases
  • Animals
  • Aspartic Acid Endopeptidases
  • Caprolactam / analogs & derivatives
  • Caprolactam / chemistry*
  • Cell Line
  • Dogs
  • Drug Design
  • Drug Evaluation, Preclinical
  • Endopeptidases / chemistry
  • Endopeptidases / drug effects*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Molecular Conformation
  • Stereoisomerism
  • Structure-Activity Relationship
  • Succinates / chemistry*

Substances

  • Enzyme Inhibitors
  • Succinates
  • Caprolactam
  • Amyloid Precursor Protein Secretases
  • Endopeptidases
  • Aspartic Acid Endopeptidases
  • BACE1 protein, human