@article {1716,
	title = {Stereochemical studies of adrenergic drugs. Optically active derivatives of imidazolines.},
	journal = {J Med Chem},
	volume = {19},
	year = {1976},
	month = {1976 Dec},
	pages = {1382-4},
	abstract = {<p>The synthesis of (R)-(+)-4-methyl-2-(1-naphthylmethyl)imidazoline hydrochloride (2) and (S)-(-)-4-methyl-2-(1-naphthylmethyl)imidazoline hydrochloride (3) is presented. The synthesis involves the preparation of (R)-(+)- and (S)-(-)-1,2-diaminopropane dihydrochloride and then allowing the appropriate diaminopropane to react with ethyl 1-naphthyliminoacetate hydrochloride in the presence of triethylamine. The parent compound, naphazoline, is a potent alpha-adrenoreceptor agonist (-log ED50 = 7.22), whereas the methylated derivatives, 2 and 3, were moderately potent antagonists (pA2 = 5.6 and 5.8, respectively) of the alpha-adrenoreceptor. Compounds 2 and 3 also produced blockade of the response to histamine on the rabbit aorta, but at concentrations approximately 20 times higher than necessary to produce equal blockade of the alpha-adrenoreceptor.</p>},
	keywords = {Animals, Aorta, Histamine H1 Antagonists, Imidazoles, In Vitro Techniques, Muscle, Smooth, Naphazoline, Phenylephrine, Rabbits, Receptors, Adrenergic, Receptors, Adrenergic, alpha, Stereoisomerism},
	issn = {0022-2623},
	author = {Miller, D D and Hsu, F L and Ruffolo, R R and Patil, P N}
}
