Structure-based optimization of morpholino-triazines as PI3K and mTOR inhibitors

Bioorg Med Chem Lett. 2012 Jan 15;22(2):1009-13. doi: 10.1016/j.bmcl.2011.12.001. Epub 2011 Dec 8.

Abstract

A virtual screen of our in-house database using various fingerprint techniques returned several triazine hits which were found to be mTOR inhibitors with a slight selectivity over PI3Kα. Using structure-guided lead optimization the inhibitory activity towards mTOR and PI3Kα was increased to the low nanomolar range. Exploiting shape differences in the binding-site allowed for the design of mTOR selective inhibitors. Focus on ligand efficiency ensured the inhibitors retained a low molecular weight and desirable drug-like properties.

MeSH terms

  • Cell Line, Tumor
  • Dose-Response Relationship, Drug
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Morpholines / chemistry
  • Morpholines / pharmacology*
  • Phosphoinositide-3 Kinase Inhibitors*
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship
  • TOR Serine-Threonine Kinases / antagonists & inhibitors*
  • Triazines / chemistry
  • Triazines / pharmacology*

Substances

  • Morpholines
  • Phosphoinositide-3 Kinase Inhibitors
  • Protein Kinase Inhibitors
  • Triazines
  • TOR Serine-Threonine Kinases