Discovery of novel 5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine derivatives as γ-secretase modulators (Part 2)

Bioorg Med Chem. 2016 Jul 15;24(14):3192-206. doi: 10.1016/j.bmc.2016.05.040. Epub 2016 May 20.

Abstract

γ-Secretase modulators (GSMs), which lower pathogenic amyloid beta (Aβ) without affecting the production of total Aβ or Notch signal, have emerged as a potential therapeutic agent for Alzheimer's disease (AD). A novel series of 5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine derivatives was discovered and characterized as GSMs. Optimization of substituents at the 8-position of the core scaffold using ligand-lipophilicity efficiency (LLE) as a drug-likeness guideline led to identification of various types of high-LLE GSMs. Phenoxy compound (R)-17 exhibited especially high LLE as well as potent in vivo Aβ42-lowering effect by single administration. Furthermore, multiple oral administration of (R)-17 significantly reduced soluble and insoluble brain Aβ42, and ameliorated cognitive deficit in novel object recognition test (NORT) using Tg2576 mice as an AD model.

Keywords: Alzheimer’s disease; Amyloid beta; γ-Secretase; γ-Secretase modulator.

MeSH terms

  • Administration, Oral
  • Amyloid Precursor Protein Secretases / antagonists & inhibitors*
  • Animals
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Mice
  • Mice, Inbred C57BL
  • Mice, Transgenic
  • Pyridines / administration & dosage
  • Pyridines / chemistry*
  • Pyridines / pharmacology*

Substances

  • Enzyme Inhibitors
  • Pyridines
  • Amyloid Precursor Protein Secretases