Synthesis and biological activity of novel substituted pyridines and purines containing 2,4-thiazolidinedione

Eur J Med Chem. 2004 May;39(5):433-47. doi: 10.1016/j.ejmech.2004.03.001.

Abstract

A series of substituted pyridines and purines containing 2,4-thiazolidinedione were designed and synthesized from their corresponding pyridines and purines. These synthesized compounds (entry no. 6a-d, 12a-e, 18a-d, 23a-c) were evaluated for their effect on triglyceride accumulation in 3T3-L1 cells in vitro and their hypoglycemic and hypolipidemic activity in the genetically diabetic KKA(y) mice in vivo. On the basis of their biological activities, 5-(4-[2-[N-methyl-(5-phenyl-pyridin-2-yl)amino]ethoxy]benzyl)thiazolidine-2,4-dione (6d) was selected as a candidate for further pharmacological studies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3T3-L1 Cells
  • Animals
  • Blood Glucose / drug effects
  • Cell Division / drug effects
  • Cells, Cultured
  • Diabetes Mellitus, Experimental / drug therapy*
  • Disease Models, Animal
  • Drug Design
  • Hepatocytes / drug effects
  • Hepatocytes / metabolism
  • Hypoglycemic Agents / administration & dosage
  • Hypoglycemic Agents / therapeutic use
  • Hypolipidemic Agents / administration & dosage
  • Hypolipidemic Agents / therapeutic use
  • Male
  • Mice
  • Molecular Structure
  • Purines / chemical synthesis*
  • Purines / pharmacology*
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacology*
  • Rats
  • Rats, Sprague-Dawley
  • Thiazolidinediones / chemistry*
  • Triglycerides / metabolism

Substances

  • Blood Glucose
  • Hypoglycemic Agents
  • Hypolipidemic Agents
  • Purines
  • Pyridines
  • Thiazolidinediones
  • Triglycerides
  • 2,4-thiazolidinedione