Identification of cyclicsulfonamide derivatives with an acetamide group as 11β-hydroxysteroid dehydrogenase 1 inhibitors

Chem Pharm Bull (Tokyo). 2011;59(1):46-52. doi: 10.1248/cpb.59.46.

Abstract

In the continuation of our 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor research, cyclic sulfonamide derivatives with an acetamide group at the 2-position were synthesized and evaluated for their abilities to inhibit 11β-HSD1. Among this series, Compound 34 showed good in vitro activity toward human 11β-HSD1, selectivity against 11β-HSD2, microsomal stability, good pharmacokinetic and safety profiles human ether-a-go-go related gene (hERG and cytochrome P450 (CYP)). Also, a docking study explained the activity difference between human and mouse 11β-HSD1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 11-beta-Hydroxysteroid Dehydrogenase Type 1 / antagonists & inhibitors*
  • 11-beta-Hydroxysteroid Dehydrogenase Type 1 / metabolism
  • 11-beta-Hydroxysteroid Dehydrogenase Type 2 / antagonists & inhibitors
  • 11-beta-Hydroxysteroid Dehydrogenase Type 2 / metabolism
  • Acetamides / chemistry*
  • Animals
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Enzyme System / metabolism
  • ERG1 Potassium Channel
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacokinetics
  • Ether-A-Go-Go Potassium Channels / antagonists & inhibitors
  • Ether-A-Go-Go Potassium Channels / metabolism
  • Humans
  • Mice
  • Sulfonamides / chemistry*
  • Thiazines / chemistry*

Substances

  • 2-(3-benzoyl-4-hydroxy-1,1-dioxido-2H-benzo(e)(1,2)thiazin-2-yl)-N- (3-(trifluoromethyl)phenyl)acetamide
  • Acetamides
  • Cytochrome P-450 Enzyme Inhibitors
  • ERG1 Potassium Channel
  • Enzyme Inhibitors
  • Ether-A-Go-Go Potassium Channels
  • KCNH2 protein, human
  • Sulfonamides
  • Thiazines
  • acetamide
  • Cytochrome P-450 Enzyme System
  • 11-beta-Hydroxysteroid Dehydrogenase Type 1
  • 11-beta-Hydroxysteroid Dehydrogenase Type 2