Optically Active Catecholimidazolines: A Study of Steric Interactions at α-Adrenoreceptors

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

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The optical isomers and deoxy form of 2-(3,4,α-trihydroxybenzyl)imidazoline hydrochloride were examined for their α-adrenergic activity on rat aorta. The rank order of stimulant activity was deoxy [formula-omited]. This is in contrast to catecholamines in which the order of activity is (R)-(-)-epinephrine > (S)-(+)-epinephrine = epinine (deoxyepinephrine). The relative order of potency for the isomers of 2-(3,4,a-trihydroxybenzyl)irnidazoline 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 α-adrenergic agonist activity, and differences observed between optical isomers were small.

Original languageEnglish (US)
Pages (from-to)957-963
Number of pages7
JournalJournal of Medicinal Chemistry
Volume26
Issue number7
DOIs
StatePublished - Jan 1 1983
Externally publishedYes

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Deoxyepinephrine
Epinephrine
Catecholamines
Imidazolines
Adrenergic Agonists
Stereoisomerism
Adrenergic Agents
Aorta

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

Cite this

Miller, D., Hamada, A., Craig, E. C., Christoph, G. G., Gallucci, J. C., Rice, P. J., ... Gallucci, J. C. (1983). Optically Active Catecholimidazolines: A Study of Steric Interactions at α-Adrenoreceptors. Journal of Medicinal Chemistry, 26(7), 957-963. https://doi.org/10.1021/jm00361a005

Optically Active Catecholimidazolines : A Study of Steric Interactions at α-Adrenoreceptors. / Miller, Duane; Hamada, Akihiko; Craig, Edward C.; Christoph, Gary G.; Gallucci, Judith C.; Rice, Peter J.; Banning, Jon W.; Patil, Popat N.; Miller, Duane D.; Hamada, Akihiko; Rice, Peter J.; Banning, Jon W.; Patil, Popat N.; Craig, Edward C.; Christoph, Gary G.; Gallucci, Judith C.

In: Journal of Medicinal Chemistry, Vol. 26, No. 7, 01.01.1983, p. 957-963.

Research output: Contribution to journalArticle

Miller, D, Hamada, A, Craig, EC, Christoph, GG, Gallucci, JC, Rice, PJ, Banning, JW, Patil, PN, Miller, DD, Hamada, A, Rice, PJ, Banning, JW, Patil, PN, Craig, EC, Christoph, GG & Gallucci, JC 1983, 'Optically Active Catecholimidazolines: A Study of Steric Interactions at α-Adrenoreceptors', Journal of Medicinal Chemistry, vol. 26, no. 7, pp. 957-963. https://doi.org/10.1021/jm00361a005
Miller, Duane ; Hamada, Akihiko ; Craig, Edward C. ; Christoph, Gary G. ; Gallucci, Judith C. ; Rice, Peter J. ; Banning, Jon W. ; Patil, Popat N. ; Miller, Duane D. ; Hamada, Akihiko ; Rice, Peter J. ; Banning, Jon W. ; Patil, Popat N. ; Craig, Edward C. ; Christoph, Gary G. ; Gallucci, Judith C. / Optically Active Catecholimidazolines : A Study of Steric Interactions at α-Adrenoreceptors. In: Journal of Medicinal Chemistry. 1983 ; Vol. 26, No. 7. pp. 957-963.
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