Pyridine amides as potent and selective inhibitors of 11beta-hydroxysteroid dehydrogenase type 1

Bioorg Med Chem Lett. 2008 Jun 1;18(11):3168-72. doi: 10.1016/j.bmcl.2008.04.069. Epub 2008 May 1.

Abstract

Several series of pyridine amides were identified as selective and potent 11beta-HSD1 inhibitors. The most potent inhibitors feature 2,6- or 3,5-disubstitution on the pyridine core. Various linkers (CH(2)SO(2), CH(2)S, CH(2)O, S, O, N, bond) between the distal aryl and central pyridyl groups are tolerated, and lipophilic amide groups are generally favored. On the distal aryl group, a number of substitutions are well tolerated. A crystal structure was obtained for a complex between 11beta-HSD1 and the most potent inhibitor in this series.

MeSH terms

  • 11-beta-Hydroxysteroid Dehydrogenase Type 1 / antagonists & inhibitors*
  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amides / pharmacology*
  • Combinatorial Chemistry Techniques
  • Crystallography, X-Ray
  • Drug Design
  • Humans
  • Inhibitory Concentration 50
  • Molecular Conformation
  • Molecular Structure
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Amides
  • Pyridines
  • 11-beta-Hydroxysteroid Dehydrogenase Type 1