Discovery of a Brain-Penetrant ATP-Competitive Inhibitor of the Mechanistic Target of Rapamycin (mTOR) for CNS Disorders

J Med Chem. 2020 Feb 13;63(3):1068-1083. doi: 10.1021/acs.jmedchem.9b01398. Epub 2020 Jan 31.

Abstract

Recent clinical evaluation of everolimus for seizure reduction in patients with tuberous sclerosis complex (TSC), a disease with overactivated mechanistic target of rapamycin (mTOR) signaling, has demonstrated the therapeutic value of mTOR inhibitors for central nervous system (CNS) indications. Given that everolimus is an incomplete inhibitor of the mTOR function, we sought to develop a new mTOR inhibitor that has improved properties and is suitable for CNS disorders. Starting from an in-house purine-based compound, optimization of the physicochemical properties of a thiazolopyrimidine series led to the discovery of the small molecule 7, a potent and selective brain-penetrant ATP-competitive mTOR inhibitor. In neuronal cell-based models of mTOR hyperactivity, 7 corrected the mTOR pathway activity and the resulting neuronal overgrowth phenotype. The new mTOR inhibitor 7 showed good brain exposure and significantly improved the survival rate of mice with neuronal-specific ablation of the Tsc1 gene. These results demonstrate the potential utility of this tool compound to test therapeutic hypotheses that depend on mTOR hyperactivity in the CNS.

MeSH terms

  • Animals
  • Anticonvulsants / metabolism
  • Anticonvulsants / pharmacokinetics
  • Anticonvulsants / therapeutic use
  • Binding Sites
  • Brain / drug effects
  • Drug Discovery
  • Humans
  • Male
  • Mice, Inbred C57BL
  • Mice, Knockout
  • Neurons / drug effects
  • Protein Binding
  • Protein Kinase Inhibitors / metabolism
  • Protein Kinase Inhibitors / pharmacokinetics
  • Protein Kinase Inhibitors / therapeutic use*
  • Pyrimidines / metabolism
  • Pyrimidines / pharmacokinetics
  • Pyrimidines / therapeutic use*
  • Rats
  • Seizures / drug therapy*
  • TOR Serine-Threonine Kinases / antagonists & inhibitors*
  • TOR Serine-Threonine Kinases / chemistry
  • TOR Serine-Threonine Kinases / metabolism
  • Thiazoles / metabolism
  • Thiazoles / pharmacokinetics
  • Thiazoles / therapeutic use*
  • Tuberous Sclerosis Complex 1 Protein / genetics

Substances

  • Anticonvulsants
  • Protein Kinase Inhibitors
  • Pyrimidines
  • Thiazoles
  • Tsc1 protein, mouse
  • Tuberous Sclerosis Complex 1 Protein
  • MTOR protein, human
  • TOR Serine-Threonine Kinases