Role of the (acyloxy)methyl moiety in eliciting the adrenergic beta-blocking activity of 3-(acyloxy)propanolamines

J Med Chem. 1987 Apr;30(4):616-22. doi: 10.1021/jm00387a006.

Abstract

Some totally aliphatic 3-(acyloxy)propanolamines were synthesized with the aim of testing whether beta-blocking activity could be obtained from this class of drugs, even in the absence of an aromatic group. The significant and, in most cases, competitive beta-blocking activity shown by the compounds under examination, together with the results of a theoretical study in which their reactivity was compared with that of other adrenergic beta-blocking drugs, seems to confirm a hypothesis previously advanced on the basis of knowledge about the action mechanism of adrenergic beta-blocking drugs and of the results of structural studies. It was also possible to suggest some considerations about the role played by the (acyloxy)methyl portion of 3-(acyloxy)propanolamines in eliciting their adrenergic beta-blocking activity.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adrenergic beta-Agonists / chemical synthesis
  • Adrenergic beta-Agonists / pharmacology*
  • Animals
  • Chemical Phenomena
  • Chemistry
  • Guinea Pigs
  • Heart Atria / drug effects
  • Male
  • Molecular Conformation
  • Propanolamines / chemical synthesis
  • Propanolamines / pharmacology*
  • Rats
  • Rats, Inbred Strains
  • Receptors, Adrenergic, beta / drug effects*
  • Structure-Activity Relationship
  • Trachea / drug effects
  • Vas Deferens / drug effects

Substances

  • Adrenergic beta-Agonists
  • Propanolamines
  • Receptors, Adrenergic, beta