Synthesis and evaluation of 2-(arylamino)imidazoles as alpha 2-adrenergic agonists

J Med Chem. 1997 Jan 3;40(1):18-23. doi: 10.1021/jm9605142.


A series of 2-(arylamino)imidazoles was synthesized and evaluated for activity at alpha 1- and alpha 2-adrenoceptors. This class of agents has been shown to have potent and selective agonist activity at the alpha 2-adrenoceptors. The most potent member of this class, 2-[(5-methyl-1,4-benzodioxan-6yl)amino]imidazole, proved efficacious for the reduction of intraocular pressure upon topical administration and for the reduction of blood pressure upon intravenous administration. During the course of our studies, we developed a new reagent that allowed rapid assembly of the target compounds. This reagent, N-(2,2-diethoxyethyl)carbodiimide, was convenient to prepare and was stable under low-temperature storage conditions.

MeSH terms

  • Adrenergic alpha-2 Receptor Agonists*
  • Animals
  • Blood-Brain Barrier / drug effects
  • Brimonidine Tartrate
  • Imidazoles / chemistry*
  • Imidazoles / pharmacology
  • Intraocular Pressure / drug effects
  • Macaca fascicularis
  • Quinoxalines / chemistry
  • Quinoxalines / pharmacology
  • Rabbits


  • Adrenergic alpha-2 Receptor Agonists
  • Imidazoles
  • Quinoxalines
  • Brimonidine Tartrate