Discovery of novel 2,6-disubstituted pyridazinone derivatives as acetylcholinesterase inhibitors

Eur J Med Chem. 2013 May:63:95-103. doi: 10.1016/j.ejmech.2013.01.056. Epub 2013 Feb 8.

Abstract

2,6-Disubstituted pyridazinone 4 was identified by HTS as a novel acetylcholinesterase (AChE) inhibitor. Under SAR development, compound 17e stood out as displaying high AChE inhibitory activity and AChE/butyrylcholinesterase (BuChE) selectivity in vitro. Docking studies revealed that 17e might interact with the catalytic active site (CAS) and the peripheral anionic site (PAS) simultaneously. Based on this novel binding information, 6-ortho-tolylamino and N-ethyl-N-isopropylacetamide substituted piperidine were disclosed as new PAS and CAS binders.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / chemistry*
  • Acetylcholinesterase / metabolism
  • Alzheimer Disease / drug therapy
  • Binding, Competitive
  • Biocatalysis / drug effects
  • Butyrylcholinesterase / chemistry*
  • Butyrylcholinesterase / metabolism
  • Catalytic Domain
  • Cholinesterase Inhibitors / chemistry*
  • Cholinesterase Inhibitors / metabolism
  • Cholinesterase Inhibitors / pharmacology
  • Drug Discovery
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Piperidines / chemistry
  • Piperidines / metabolism
  • Protein Binding
  • Protein Structure, Tertiary
  • Pyridazines / chemistry*
  • Pyridazines / metabolism
  • Pyridazines / pharmacology
  • Structure-Activity Relationship

Substances

  • Cholinesterase Inhibitors
  • Piperidines
  • Pyridazines
  • piperidine
  • Acetylcholinesterase
  • Butyrylcholinesterase