Stereochemical studies of adrenergic drugs. Optically active derivatives of imidazolines

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Abstract
The synthesis of the R(2)- and S(3)-enantimers of 4-methyl-2-(1-naphthylmethyl)-imidazoline hydrochloride was presented. The synthesis involved the preparation of (R)-(+)- and (S)-(-)-1,2-diaminopropane dihydrochloride and then allows the appropriate diaminopropane to react with ethyl 1-naphthyliminoacetate hydrochloride in the presence of triethylamine. The parent compound, naphazoline, was a potent .alpha.-adrenoreceptor agonist; the methylated derivatives more moderately potent antagonists 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.