Details

Autor(en) / Beteiligte

• Miller, Duane D
• Hamada, Akihiko
• Craig, Edward C
• Christoph, Gary G
• Galluci, Judith C
• Rice, Peter J
• Banning, Jon W
• Patil, Popat N

Titel

Optically active catecholimidazolines: a study of steric interactions at .alpha.-adrenoreceptors

Ist Teil von

• Journal of medicinal chemistry, 1983-07, Vol.26 (7), p.957-963

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

1983

Quelle

MEDLINE

Beschreibungen/Notizen

• The optical isomers and deoxy form of 2-(3,4, alpha-trihydroxybenzyl)imidazoline hydrochloride were examined for their alpha-adrenergic activity on rat aorta. The rank order of stimulant activity was deoxy (2) congruent to (R)-(-)-1 greater than (S)-(+)-1. This is in contrast to catecholamines in which the order of activity is (R)-(-)-epinephrine greater than (S)-(+)-epinephrine = epinine (deoxyepinephrine). The relative order of potency for the isomers of 2-(3,4, alpha-trihydroxybenzyl)imidazoline is different than that predicted by the Easson--Stedman theory for stereoisomers of catecholamines. Also, substitution of the deoxy compound 2 with substituents, methyl or benzyl, in the 4-position lowers the alpha-adrenergic agonist activity, and differences observed between optical isomers were small.