Substituted phenanthrene imidazoles as potent, selective, and orally active mPGES-1 inhibitors

Bioorg Med Chem Lett. 2007 Dec 15;17(24):6816-20. doi: 10.1016/j.bmcl.2007.10.033. Epub 2007 Oct 17.

Abstract

Phenanthrene imidazole 3 (MF63) has been identified as a novel potent, selective, and orally active mPGES-1 inhibitor. This new series was developed by lead optimization of a hit from an internal HTS campaign. Compound 3 is significantly more potent than the previously reported indole carboxylic acid 1 with an A549 whole cell IC(50) of 0.42 microM (50% FBS) and a human whole blood IC(50) of 1.3 microM. It exhibited a significant analgesic effect in a guinea pig hyperalgesia model when orally dosed at 30 and 100mg/kg.

MeSH terms

  • Analgesics, Non-Narcotic / blood
  • Analgesics, Non-Narcotic / chemical synthesis*
  • Analgesics, Non-Narcotic / chemistry
  • Analgesics, Non-Narcotic / pharmacology
  • Animals
  • Disease Models, Animal
  • Drug Design
  • Guinea Pigs
  • Humans
  • Hyperalgesia / chemically induced
  • Imidazoles / blood
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Imidazoles / pharmacology*
  • Inhibitory Concentration 50
  • Intramolecular Oxidoreductases / antagonists & inhibitors*
  • Molecular Structure
  • Phenanthrenes / blood
  • Phenanthrenes / chemical synthesis*
  • Phenanthrenes / chemistry
  • Phenanthrenes / pharmacology*
  • Prostaglandin-E Synthases
  • Rats
  • Structure-Activity Relationship

Substances

  • Analgesics, Non-Narcotic
  • Imidazoles
  • MF63 compound
  • Phenanthrenes
  • Intramolecular Oxidoreductases
  • PTGES protein, human
  • Prostaglandin-E Synthases