N-Substituted Imidazolines and Ethylenediamines and Their Action on α-and β-Adrenergic Receptors

A. Hamada, Emily L. Yaden, J. S. Horng, Robert R. Ruffolo, Popat N. Patil, Duane Miller

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A series of N-substituted imidazolines and ethylenediamines were synthesized and examined for their activity in α-and β-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-Dihydroxy-phenyl)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 α2-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 α1 adrenergic receptors in a pithed rat model. Of the four compounds examined, only compound 2 showed significant direct activity on β1 and β2-adrenergic receptors.

Original languageEnglish (US)
Pages (from-to)1269-1273
Number of pages5
JournalJournal of Medicinal Chemistry
Volume28
Issue number9
DOIs
StatePublished - Jan 1 1985
Externally publishedYes

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ethylenediamine
Ethylenediamines
Imidazolines
Adrenergic Receptors
Amines
Adrenergic Agents
catechol

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

Cite this

N-Substituted Imidazolines and Ethylenediamines and Their Action on α-and β-Adrenergic Receptors. / Hamada, A.; Yaden, Emily L.; Horng, J. S.; Ruffolo, Robert R.; Patil, Popat N.; Miller, Duane.

In: Journal of Medicinal Chemistry, Vol. 28, No. 9, 01.01.1985, p. 1269-1273.

Research output: Contribution to journalArticle

Hamada, A. ; Yaden, Emily L. ; Horng, J. S. ; Ruffolo, Robert R. ; Patil, Popat N. ; Miller, Duane. / N-Substituted Imidazolines and Ethylenediamines and Their Action on α-and β-Adrenergic Receptors. In: Journal of Medicinal Chemistry. 1985 ; Vol. 28, No. 9. pp. 1269-1273.
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