Synthesis of 1-Substituted Analogues of Trimetoquinol Possessing Differential and Selective β-Adrenergic Properties

Duane Miller, Peter Osei-Gyimah, Rajeswari V. Raman, Dennis R. Feller

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The synthesis of the 1,1-disubstituted tetrahydroisoquinoline analogues, 1-methyl-1-(3,4,5-trimethoxybenzyl)-6,7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline hydrochloride (2) and 1-benzyl-1-(3,4,5-trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3), is described. The profile of β-adrenergic activity for these analogues was determined and compared to that of trimetoquinol (1) in isolated guinea pig atrial, tracheal, and rat adipocyte preparations. Unexpected selective β1-blocking activity in guinea pig trachea was noted with analogue 3. With the exception of 2 in guinea pig atria, 2 and 3 did not possess any β-stimulant activity. Substitution at the 1 position of trimetoquinol (1) has revealed qualitative differences in β-adrenergic activity.

Original languageEnglish (US)
Pages (from-to)1502-1504
Number of pages3
JournalJournal of Medicinal Chemistry
Volume20
Issue number11
DOIs
StatePublished - Nov 1 1977
Externally publishedYes

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Tretoquinol
Adrenergic Agents
Guinea Pigs
Tetrahydroisoquinolines
Trachea
Adipocytes
1,2,3,4-tetrahydroisoquinoline

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

Cite this

Synthesis of 1-Substituted Analogues of Trimetoquinol Possessing Differential and Selective β-Adrenergic Properties. / Miller, Duane; Osei-Gyimah, Peter; Raman, Rajeswari V.; Feller, Dennis R.

In: Journal of Medicinal Chemistry, Vol. 20, No. 11, 01.11.1977, p. 1502-1504.

Research output: Contribution to journalArticle

Miller, Duane ; Osei-Gyimah, Peter ; Raman, Rajeswari V. ; Feller, Dennis R. / Synthesis of 1-Substituted Analogues of Trimetoquinol Possessing Differential and Selective β-Adrenergic Properties. In: Journal of Medicinal Chemistry. 1977 ; Vol. 20, No. 11. pp. 1502-1504.
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