Dissociated nonsteroidal glucocorticoid receptor modulators; discovery of the agonist trigger in a tetrahydronaphthalene-benzoxazine series

J Med Chem. 2006 Jul 13;49(14):4216-31. doi: 10.1021/jm060302x.

Abstract

The tetrahydronaphthalene-benzoxazine glucocorticoid receptor (GR) partial agonist 4b was optimized to produce potent full agonists of GR. Aromatic ring substitution of the tetrahydronaphthalene leads to weak GR antagonists. Discovery of an "agonist trigger" substituent on the saturated ring of the tetrahydronaphthalene leads to increased potency and efficacious GR agonism. These compounds are efficacy selective in an NFkB GR agonist assay (representing transrepression effects) over an MMTV GR agonist assay (representing transactivation effects). 52 and 60 have NFkB pIC(50) = 8.92 (105%) and 8.69 (92%) and MMTV pEC(50) = 8.20 (47%) and 7.75 (39%), respectively. The impact of the trigger substituent on agonism is modeled within GR and discussed. 36, 52, and 60 have anti-inflammatory activity in a mouse model of inflammation after topical dosing with 52 and 60, having an effect similar to that of dexamethasone. The original lead was discovered by a manual agreement docking method, and automation of this method is also described.

MeSH terms

  • Administration, Topical
  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Benzoxazines / chemical synthesis*
  • Benzoxazines / chemistry
  • Benzoxazines / pharmacology
  • Binding, Competitive
  • Cell Line
  • Dexamethasone / pharmacology
  • Humans
  • Hypersensitivity, Delayed / drug therapy
  • Mice
  • Models, Molecular
  • Radioligand Assay
  • Receptors, Glucocorticoid / agonists*
  • Receptors, Glucocorticoid / antagonists & inhibitors
  • Receptors, Glucocorticoid / genetics
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tetrahydronaphthalenes / chemical synthesis*
  • Tetrahydronaphthalenes / chemistry
  • Tetrahydronaphthalenes / pharmacology
  • Transcription, Genetic / drug effects
  • Transcriptional Activation / drug effects

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Benzoxazines
  • Receptors, Glucocorticoid
  • Tetrahydronaphthalenes
  • Dexamethasone