Discovery of 2-((1H-benzo[d]imidazol-1-yl)methyl)-4H-pyrido[1,2-a]pyrimidin-4-ones as novel PKM2 activators

Bioorg Med Chem Lett. 2013 Jun 1;23(11):3358-63. doi: 10.1016/j.bmcl.2013.03.090. Epub 2013 Apr 1.

Abstract

The M2 isoform of pyruvate kinase is an emerging target for antitumor therapy. In this letter, we describe the discovery of 2-((1H-benzo[d]imidazol-1-yl)methyl)-4H-pyrido[1,2-a]pyrimidin-4-ones as potent and selective PKM2 activators which were found to have a novel binding mode. The original lead identified from high throughput screening was optimized into an efficient series via computer-aided structure-based drug design. Both a representative compound from this series and an activator described in the literature were used as molecular tools to probe the biological effects of PKM2 activation on cancer cells. Our results suggested that PKM2 activation alone is not sufficient to alter cancer cell metabolism.

MeSH terms

  • Benzimidazoles / chemistry*
  • Binding Sites
  • Carrier Proteins / agonists*
  • Carrier Proteins / metabolism
  • Cell Line
  • Computer-Aided Design
  • Drug Evaluation, Preclinical
  • High-Throughput Screening Assays
  • Humans
  • Kinetics
  • Membrane Proteins / agonists*
  • Membrane Proteins / metabolism
  • Molecular Docking Simulation
  • Protein Binding
  • Protein Structure, Tertiary
  • Pyrimidinones / chemical synthesis
  • Pyrimidinones / chemistry*
  • Pyrimidinones / metabolism
  • Structure-Activity Relationship
  • Thyroid Hormone-Binding Proteins
  • Thyroid Hormones / agonists*
  • Thyroid Hormones / metabolism

Substances

  • Benzimidazoles
  • Carrier Proteins
  • Membrane Proteins
  • Pyrimidinones
  • Thyroid Hormones
  • benzimidazole