Stereochemical Studies of Adrenergic Drugs. Optically Active Derivatives of Imidazolines

Duane Miller, Fu Lian Hsu, Robert R. Ruffolo, Popat N. Patil

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The synthesis of (R)-(+)-4-methyl-2-(1-naphthylmethyl)imidazoline hydrochloride (2) and (S)-(-)-4-methyl-2-(1-naphthylmethyl)imidazoline hydrochloride (3) is presented. The synthesis involves the preparation of (R)-(+)- and (S)-(-)-1,2-diaminopropane dihydrochloride and then allowing the appropriate diaminopropane to react with ethyl 1-naphthyliminoacetate hydrochloride in the presence of triethylamine. The parent compound, naphazoline, is a potent α-adrenoreceptor agonist (-log ED50 = 7.22), whereas the methylated derivatives, 2 and 3, were moderately potent antagonists (pA2 = 5.6 and 5.8, respectively) of the α-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 α-adrenoreceptor.

Original languageEnglish (US)
Pages (from-to)1382-1384
Number of pages3
JournalJournal of Medicinal Chemistry
Volume19
Issue number12
DOIs
StatePublished - Dec 1 1976
Externally publishedYes

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Naphazoline
Imidazolines
Adrenergic Agents
Histamine
Aorta
Rabbits
triethylamine
2-imidazoline
1,2-diaminopropane

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

Cite this

Stereochemical Studies of Adrenergic Drugs. Optically Active Derivatives of Imidazolines. / Miller, Duane; Hsu, Fu Lian; Ruffolo, Robert R.; Patil, Popat N.

In: Journal of Medicinal Chemistry, Vol. 19, No. 12, 01.12.1976, p. 1382-1384.

Research output: Contribution to journalArticle

Miller, Duane ; Hsu, Fu Lian ; Ruffolo, Robert R. ; Patil, Popat N. / Stereochemical Studies of Adrenergic Drugs. Optically Active Derivatives of Imidazolines. In: Journal of Medicinal Chemistry. 1976 ; Vol. 19, No. 12. pp. 1382-1384.
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