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N-substituted Imidazolines and Ethylenediamines and Their Action on Alpha- And Beta-Adrenergic Receptors

N-substituted Imidazolines and Ethylenediamines and Their Action on Alpha- And Beta-Adrenergic Receptors

A Hamada, E L Yaden, J S Horng, R R Ruffolo Jr, P N Patil, D D Miller

J Med Chem. 1985 Sep;28(9):1269-73.

PMID: 2993616

Abstract:

A series of N-substituted imidazolines and ethylenediamines were synthesized and examined for their activity in alpha- and beta-adrenergic systems. The length of the intermediate side chain between the catechol and imidazoline ring or the amine of the ethylenediamine segment was shown to affect the adrenergic activity. N-[2-(3,4-Dihydroxyphenyl)ethyl]imidazoline hydrochloride (2) and N-[2-(3,4-dihydroxyphenyl)ethyl]ethylenediamine dihydrochloride (4), both with two methylene groups between the catechol and amine segment, were found to be somewhat selective for alpha 2-adrenergic receptors while 1-(3,4-dihydroxybenzyl)imidazoline hydrochloride (1) and N-2-(3,4-dihydroxybenzyl)ethylenediamine dihydrochloride (3), both with one methylene group between the catechol and amine segment, were more selective for alpha1-adrenergic receptors in a pithed rat model. Of the four compounds examined, only compound 2 showed significant direct activity on beta1- and beta2-adrenergic receptors.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP40600133	Cirazoline hydrochloride		40600-13-3	Price

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