Synthesis and evaluation of the pharmacological activity of rigid analogues of sympathomimetic catecholamines derived from bicyclo[2.2.1]heptane

J Med Chem. 1989 Apr;32(4):856-9. doi: 10.1021/jm00124a020.

Abstract

endo-3-Amino-exo-2-(3,4-dihydroxyphenyl)-2-hydroxybicyclo[2.2.1]he ptane (4a) and its N-isopropyl derivative (4b) were synthesized and assayed for their adrenergic activity on various isolated preparations. Compounds 4a and 4b, tested up to a dose of 10(-4) M, did not reveal any activity, either stimulant or blocking, on the alpha- and beta-adrenoceptors. Possible rationalizations of the results obtained, however, are suggested.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Atrial Function
  • Bridged Bicyclo Compounds / chemical synthesis
  • Bridged Bicyclo Compounds / pharmacology*
  • Bridged-Ring Compounds / pharmacology*
  • Catecholamines / chemical synthesis
  • Catecholamines / pharmacology*
  • Chemical Phenomena
  • Chemistry
  • Guinea Pigs
  • Heart Atria / drug effects
  • Male
  • Molecular Conformation
  • Rats
  • Rats, Inbred Strains
  • Receptors, Adrenergic, alpha / drug effects*
  • Receptors, Adrenergic, alpha / physiology
  • Receptors, Adrenergic, beta / drug effects*
  • Receptors, Adrenergic, beta / physiology
  • Structure-Activity Relationship
  • Trachea / drug effects
  • Trachea / physiology
  • Vas Deferens / drug effects
  • Vas Deferens / physiology

Substances

  • Bridged Bicyclo Compounds
  • Bridged-Ring Compounds
  • Catecholamines
  • Receptors, Adrenergic, alpha
  • Receptors, Adrenergic, beta
  • 3-amino-2-(3,4-dihydroxyphenyl)-2-hydroxybicyclo(2.2.1)heptane
  • N-isopropyl-3-amino-2-(3,4-dihydroxyphenyl)-2-hydroxybicyclo(2.2.1)heptane