Synthesis and biological activity of [[(heterocycloamino)alkoxy] benzyl]-2,4-thiazolidinediones as PPARgamma agonists

Arch Pharm Res. 2006 May;29(5):394-9. doi: 10.1007/BF02968589.

Abstract

Benzothiazole derivatives of thiazolidinediones (TZD) were synthesized using a modified Mitsunobu reaction of 2-(benzothiazol-2-ylmethylamino)ethanol (2) with 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione and assayed for activity on peroxisome proliferator-activated receptor (PPAR) subtypes and inhibitory activity of NO production in lipopolysaccharide-activated macrophages. Most of the tested compounds were identified as potent PPARgamma agonists, indicating their potential as drug candidates for diabetes.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzothiazoles / chemical synthesis
  • Benzothiazoles / pharmacology
  • Cell Line
  • Dose-Response Relationship, Drug
  • Hypoglycemic Agents / chemical synthesis
  • Hypoglycemic Agents / pharmacology*
  • Lipopolysaccharides
  • Macrophages / drug effects*
  • Macrophages / metabolism
  • Mice
  • Molecular Structure
  • Nitrites / metabolism
  • PPAR gamma / agonists*
  • PPAR gamma / genetics
  • Structure-Activity Relationship
  • Thiazolidinediones / chemical synthesis
  • Thiazolidinediones / pharmacology*
  • Transfection

Substances

  • Benzothiazoles
  • Hypoglycemic Agents
  • Lipopolysaccharides
  • Nitrites
  • PPAR gamma
  • Thiazolidinediones