Discovery of adamantane ethers as inhibitors of 11beta-HSD-1: Synthesis and biological evaluation

Bioorg Med Chem Lett. 2007 Feb 1;17(3):750-5. doi: 10.1016/j.bmcl.2006.10.074. Epub 2006 Oct 28.

Abstract

A novel class of adamantane ethers 11beta-hydroxysteroid hydrogenase type I inhibitors has been discovered. These compounds have excellent HSD-1 potency and selectivity against HSD-2. The structure-activity relationships, selectivity, metabolism, PK, ex vivo pharmacodynamic data, and an X-ray crystal structure of one of these inhibitors bound to h-HSD-1 are discussed.

MeSH terms

  • 11-beta-Hydroxysteroid Dehydrogenase Type 1 / antagonists & inhibitors*
  • 11-beta-Hydroxysteroid Dehydrogenase Type 1 / genetics
  • Adamantane / analogs & derivatives*
  • Adamantane / chemical synthesis
  • Adamantane / pharmacology*
  • Alkylation
  • Animals
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Ethers / chemical synthesis
  • Ethers / pharmacology
  • Half-Life
  • Humans
  • Indicators and Reagents
  • Mice
  • Mice, Knockout
  • Microsomes, Liver / enzymology
  • Microsomes, Liver / metabolism
  • Models, Molecular

Substances

  • Enzyme Inhibitors
  • Ethers
  • Indicators and Reagents
  • 11-beta-Hydroxysteroid Dehydrogenase Type 1
  • Adamantane