Design and synthesis of new nonsteroidal glucocorticoid modulators through application of an "agreement docking" method

J Med Chem. 2005 Jul 14;48(14):4507-10. doi: 10.1021/jm050345y.

Abstract

Structurally related glucocorticoid receptor (GR) binders were docked into the GR active site to select the binding mode closest to the true docking mode. This process, termed an "agreement docking method", led to the design of tetrahydronaphthalene 9. The method was validated by the syntheses of 9 and related analogues, which are potent binders of GR. 15a is a partial agonist while 9e and 15a are micromolar antagonists in a mouse mammary tumor virus transactivation assay.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology
  • Cell Line
  • Cell Line, Tumor
  • Humans
  • Ligands
  • Mice
  • Models, Molecular
  • Receptors, Glucocorticoid / agonists*
  • Receptors, Glucocorticoid / antagonists & inhibitors*
  • Receptors, Glucocorticoid / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tetrahydronaphthalenes / chemical synthesis*
  • Tetrahydronaphthalenes / chemistry
  • Tetrahydronaphthalenes / pharmacology
  • Transcription, Genetic / drug effects
  • Transcriptional Activation / drug effects

Substances

  • Anti-Inflammatory Agents
  • Ligands
  • Receptors, Glucocorticoid
  • Tetrahydronaphthalenes