Synthesis and adrenolytic activity of 1-(1H-indol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol and its enantiomers. Part 1

Eur J Med Chem. 2009 Feb;44(2):809-17. doi: 10.1016/j.ejmech.2008.05.019. Epub 2008 Jul 2.

Abstract

The synthesis of (2RS)-1-(1H-indol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol ((RS)-9) and its enantiomers has been described and tested for electrocardiographic, antiarrhythmic, hypotensive and spasmolytic activities as well as for alpha(1)-, alpha(2)- and beta(1)-adrenoceptors' binding affinities. All compounds significantly decrease systolic and diastolic blood pressure, and possess antiarrhythmic activity and affinity to alpha(1)-, alpha(2)- and beta(1)-adrenoceptors. The results suggest that the antiarrhythmic and hypotensive effects of these compounds are related to their adrenolytic but not spasmolytic properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Propanol
  • Adrenergic Antagonists / chemical synthesis*
  • Adrenergic Antagonists / pharmacology
  • Animals
  • Anti-Arrhythmia Agents / chemical synthesis
  • Arrhythmias, Cardiac / drug therapy
  • Electrocardiography
  • Hypotension / drug therapy
  • Indoles / chemical synthesis*
  • Indoles / pharmacology
  • Parasympatholytics / chemical synthesis
  • Propanolamines / chemical synthesis*
  • Propanolamines / pharmacology
  • Propanols / chemical synthesis*
  • Propanols / pharmacology
  • Rabbits
  • Rats
  • Receptors, Adrenergic / metabolism*
  • Receptors, Adrenergic, alpha-1 / metabolism
  • Receptors, Adrenergic, beta-1 / metabolism
  • Spasm / drug therapy
  • Stereoisomerism

Substances

  • 1-(1H-indol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)propan-2-ol
  • Adrenergic Antagonists
  • Anti-Arrhythmia Agents
  • Indoles
  • Parasympatholytics
  • Propanolamines
  • Propanols
  • Receptors, Adrenergic
  • Receptors, Adrenergic, alpha-1
  • Receptors, Adrenergic, beta-1
  • 2-Propanol