Conformationally defined adrenergic agents. 5. Resolution, absolute configuration, and pharmacological characterization of the enantiomers of 2-(5,6-dihydroxy-1,2,3,4-tetrahydro-1-naphthyl)imidazoline: a potent agonist at alpha-adrenoceptors.
(+/-)-2-(5,6-Dimethoxy-1,2,3,4-tetrahydro-1-naphthyl)imidazoline has been resolved into its (+) and (-) enantiomers, and the absolute configuration was established by single-crystal X-ray diffraction studies. The more active isomer has been assigned the R absolute configuration. Cleavage of the respective (+)- and (-)-dimethyl ethers with boron tribromide provided the corresponding (+)- and (-)-2-(5,6-dihydroxy-1,2,3,4-tetrahydro-1-naphthl)imidazoline hydrobromides and these were pharmacologically characterized. In various preparations, the R enantiomer has been shown to be an extremely potent alpha agonist with preferential activity at the alpha 2-adrenergic receptor.
D000316:Adrenergic alpha-Agonists / Q000494:pharmacology*; D000818:Animals; D004285:Dogs; D005260:Female; D007093:Imidazoles / Q000494:pharmacology*; D066298:In Vitro Techniques; D008297:Male; D008968:Molecular Conformation; D009281:Naphthalenes / Q000494:pharmacology*; D009638:Norepinephrine / Q000494:pharmacology; D011817:Rabbits; D051381:Rats; D011919:Rats, Inbred Strains; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000494:pharmacology*; D014961:X-Ray Diffraction
D000316:Adrenergic alpha-Agonists; D007093:Imidazoles; D009281:Naphthalenes; D013764:Tetrahydronaphthalenes; C052396:2-(5,6-dihydroxy-1,2,3,4-tetrahydro-1-naphthyl)imidazoline; D009638:Norepinephrine