Design, Structure-Activity Relationships, and In Vivo Evaluation of Potent and Brain-Penetrant Imidazo[1,2- b]pyridazines as Glycogen Synthase Kinase-3β (GSK-3β) Inhibitors

J Med Chem. 2023 Mar 23;66(6):4231-4252. doi: 10.1021/acs.jmedchem.3c00133. Epub 2023 Mar 9.

Abstract

Glycogen synthase kinase-3 (GSK-3) is a serine/threonine kinase that regulates numerous cellular processes, including metabolism, proliferation, and cell survival. Due to its multifaceted role, GSK-3 has been implicated in a variety of diseases, including Alzheimer's disease, type 2 diabetes, cancer, and mood disorders. GSK-3β has been linked to the formation of the neurofibrillary tangles associated with Alzheimer's disease that arise from the hyperphosphorylation of tau protein. The design and synthesis of a series of imidazo[1,2-b]pyridazine derivatives that were evaluated as GSK-3β inhibitors are described herein. Structure-activity relationship studies led to the identification of potent GSK-3β inhibitors. In vivo studies with 47 in a triple-transgenic mouse Alzheimer's disease model showed that this compound is a brain-penetrant, orally bioavailable GSK-3β inhibitor that significantly lowered levels of phosphorylated tau.

MeSH terms

  • Alzheimer Disease* / metabolism
  • Animals
  • Brain / metabolism
  • Diabetes Mellitus, Type 2*
  • Glycogen Synthase Kinase 3 / metabolism
  • Glycogen Synthase Kinase 3 beta / metabolism
  • Mice
  • Mice, Transgenic
  • Phosphorylation
  • Structure-Activity Relationship
  • tau Proteins / metabolism

Substances

  • Glycogen Synthase Kinase 3 beta
  • Glycogen Synthase Kinase 3
  • tau Proteins