Synthesis, β-Adrenergic Activity, and Platelet Antiaggregatory Activity of a Positional Isomer of Trimetoquinol: 1-(2', 4', 5'-Trimethoxybenzyl)-6, 7-Dihydroxy-l, 2, 3, 4-Tetrahydroisoquinoline

Duane Miller, Josef F. Bossart, Joseph R. Mayo, Dennis R. Feller

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A positional isomer of trimetoquinol (1), l-(2', 4', 5'-trimethoxybenzyl)-6, 7-dihydroxy-l, 2, 3, 4-tetrahydroisoquinoline (3), was synthesized and found to possess less β-adrenergic activity than 1 in isolated guinea pig atrial and tracheal preparations. The analogue 3 was an effective antiaggregatory agent in human and rabbit platelet-rich plasma preparations, while 1 was effective only as an inhibitor of arachidonic acid induced aggregation in human platelets. These findings indicate that both qualitative and quantitative differences in biological activity have occurred as a result of changing the position of the methoxy groups on the 1-benzyl substituent of 1.

Original languageEnglish (US)
Pages (from-to)331-333
Number of pages3
JournalJournal of Medicinal Chemistry
Volume23
Issue number3
DOIs
StatePublished - Jan 1 1980

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Tetrahydroisoquinolines
Adrenergic Agents
Tretoquinol
Blood Platelets
Platelet-Rich Plasma
Arachidonic Acid
Guinea Pigs
Rabbits
1-(2',4',5-trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

Cite this

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title = "Synthesis, β-Adrenergic Activity, and Platelet Antiaggregatory Activity of a Positional Isomer of Trimetoquinol: 1-(2', 4', 5'-Trimethoxybenzyl)-6, 7-Dihydroxy-l, 2, 3, 4-Tetrahydroisoquinoline",
abstract = "A positional isomer of trimetoquinol (1), l-(2', 4', 5'-trimethoxybenzyl)-6, 7-dihydroxy-l, 2, 3, 4-tetrahydroisoquinoline (3), was synthesized and found to possess less β-adrenergic activity than 1 in isolated guinea pig atrial and tracheal preparations. The analogue 3 was an effective antiaggregatory agent in human and rabbit platelet-rich plasma preparations, while 1 was effective only as an inhibitor of arachidonic acid induced aggregation in human platelets. These findings indicate that both qualitative and quantitative differences in biological activity have occurred as a result of changing the position of the methoxy groups on the 1-benzyl substituent of 1.",
author = "Duane Miller and Bossart, {Josef F.} and Mayo, {Joseph R.} and Feller, {Dennis R.}",
year = "1980",
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doi = "10.1021/jm00177a027",
language = "English (US)",
volume = "23",
pages = "331--333",
journal = "Journal of Medicinal Chemistry",
issn = "0022-2623",
publisher = "American Chemical Society",
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TY - JOUR

T1 - Synthesis, β-Adrenergic Activity, and Platelet Antiaggregatory Activity of a Positional Isomer of Trimetoquinol

T2 - 1-(2', 4', 5'-Trimethoxybenzyl)-6, 7-Dihydroxy-l, 2, 3, 4-Tetrahydroisoquinoline

AU - Miller, Duane

AU - Bossart, Josef F.

AU - Mayo, Joseph R.

AU - Feller, Dennis R.

PY - 1980/1/1

Y1 - 1980/1/1

N2 - A positional isomer of trimetoquinol (1), l-(2', 4', 5'-trimethoxybenzyl)-6, 7-dihydroxy-l, 2, 3, 4-tetrahydroisoquinoline (3), was synthesized and found to possess less β-adrenergic activity than 1 in isolated guinea pig atrial and tracheal preparations. The analogue 3 was an effective antiaggregatory agent in human and rabbit platelet-rich plasma preparations, while 1 was effective only as an inhibitor of arachidonic acid induced aggregation in human platelets. These findings indicate that both qualitative and quantitative differences in biological activity have occurred as a result of changing the position of the methoxy groups on the 1-benzyl substituent of 1.

AB - A positional isomer of trimetoquinol (1), l-(2', 4', 5'-trimethoxybenzyl)-6, 7-dihydroxy-l, 2, 3, 4-tetrahydroisoquinoline (3), was synthesized and found to possess less β-adrenergic activity than 1 in isolated guinea pig atrial and tracheal preparations. The analogue 3 was an effective antiaggregatory agent in human and rabbit platelet-rich plasma preparations, while 1 was effective only as an inhibitor of arachidonic acid induced aggregation in human platelets. These findings indicate that both qualitative and quantitative differences in biological activity have occurred as a result of changing the position of the methoxy groups on the 1-benzyl substituent of 1.

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U2 - 10.1021/jm00177a027

DO - 10.1021/jm00177a027

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