Imidazo[2,1-b]thiazole system: a scaffold endowing dihydropyridines with selective cardiodepressant activity

J Med Chem. 2008 Mar 27;51(6):1592-600. doi: 10.1021/jm070681+. Epub 2008 Feb 28.

Abstract

The synthesis, characterization, and functional in vitro assays in cardiac tissues and smooth muscle (vascular and nonvascular) of a number of 4-imidazo[2,1- b]thiazole-1,4-dihydropyridines are reported. The binding properties for the novel compounds have been investigated and the interaction with the binding site common to other aryl-dihydropyridines has been demonstrated. Interestingly, the novel 4-aryl-dihydropyridines are L-type calcium channel blockers with a peculiar pharmacological behavior. Indeed, the imidazo[2,1- b]thiazole system is found to confer to the dihydropyridine scaffold an inotropic and/or chronotropic cardiovascular activity with a high selectivity toward the nonvascular tissue. Finally, molecular modeling studies were undertaken for the most representative compounds with the aim of describing the binding properties of the new ligands at molecular level and to rationalize the found structure-activity relationship data. Due to the observed pharmacological behavior of our compounds, they might be promising agents for the treatment of specific cardiovascular pathologies such as cardiac hypertrophy and ischemia.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding Sites
  • Computer Simulation
  • Dihydropyridines / chemical synthesis
  • Dihydropyridines / chemistry
  • Dihydropyridines / pharmacology*
  • Drug Design
  • Drug Evaluation, Preclinical
  • Guinea Pigs
  • Heart / drug effects*
  • Heart Rate / drug effects*
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry
  • Imidazoles / pharmacology*
  • Ligands
  • Models, Molecular
  • Molecular Structure
  • Muscle, Smooth, Vascular / drug effects
  • Myocardial Contraction / drug effects*
  • Myocytes, Cardiac / drug effects
  • Small Molecule Libraries
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / pharmacology*

Substances

  • Dihydropyridines
  • Imidazoles
  • Ligands
  • Small Molecule Libraries
  • Thiazoles
  • 1,4-dihydropyridine