title: Synthesis and evaluation of 2-(arylamino)imidazoles as alpha 2-adrenergic agonists.
abstract: 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.
authors.affiliation: Allergan Pharmaceuticals, Irvine, California 92612, USA.
authors.forename: S A
authors.initials: SA
authors.lastname: Munk
authors.forename: D A
authors.initials: DA
authors.lastname: Harcourt
authors.forename: P N
authors.initials: PN
authors.lastname: Arasasingham
authors.forename: J A
authors.initials: JA
authors.lastname: Burke
authors.forename: A B
authors.initials: AB
authors.lastname: Kharlamb
authors.forename: C A
authors.initials: CA
authors.lastname: Manlapaz
authors.forename: E U
authors.initials: EU
authors.lastname: Padillo
authors.forename: D
authors.initials: D
authors.lastname: Roberts
authors.forename: E
authors.initials: E
authors.lastname: Runde
authors.forename: L
authors.initials: L
authors.lastname: Williams
authors.forename: L A
authors.initials: LA
authors.lastname: Wheeler
authors.forename: M E
authors.initials: ME
authors.lastname: Garst
mesh_terms: D058647:Adrenergic alpha-2 Receptor Agonists; D000818:Animals; D001812:Blood-Brain Barrier / Q000187:drug effects; D000068438:Brimonidine Tartrate; D007093:Imidazoles / Q000737:chemistry* / Q000494:pharmacology; D007429:Intraocular Pressure / Q000187:drug effects; D008252:Macaca fascicularis; D011810:Quinoxalines / Q000737:chemistry / Q000494:pharmacology; D011817:Rabbits
chemical_list: D058647:Adrenergic alpha-2 Receptor Agonists; D007093:Imidazoles; D011810:Quinoxalines; D000068438:Brimonidine Tartrate