BACE-1 inhibitors part 2: identification of hydroxy ethylamines (HEAs) with reduced peptidic character

Bioorg Med Chem Lett. 2008 Feb 1;18(3):1017-21. doi: 10.1016/j.bmcl.2007.12.019. Epub 2007 Dec 15.

Abstract

This paper describes the discovery of non-peptidic, potent, and selective hydroxy ethylamine (HEA) inhibitors of BACE-1 by replacement of the prime side of a lead di-amide 2. Inhibitors with nanosmolar potency and high selectivity were identified. Depending on the nature of the P(1)(') and P(2)(') substituents, two different binding modes were observed in X-ray co-crystal structures.

MeSH terms

  • Alzheimer Disease / drug therapy
  • Alzheimer Disease / metabolism*
  • Amyloid Precursor Protein Secretases / antagonists & inhibitors*
  • Amyloid beta-Protein Precursor / antagonists & inhibitors
  • Aspartic Acid Endopeptidases / antagonists & inhibitors*
  • Combinatorial Chemistry Techniques*
  • Crystallography, X-Ray
  • Ethylamines / chemical synthesis*
  • Ethylamines / chemistry
  • Ethylamines / pharmacology*
  • Humans
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Amyloid beta-Protein Precursor
  • Ethylamines
  • Amyloid Precursor Protein Secretases
  • Aspartic Acid Endopeptidases
  • BACE1 protein, human
  • ethylamine