Conformational effects on the activity of drugs. 7. Synthesis and pharmacological properties of 2-(p-nitrophenyl)-substituted morpholines

J Med Chem. 1979 Jun;22(6):738-41. doi: 10.1021/jm00192a023.

Abstract

A series of 1-(p-nitrophenyl)-2-aminoethanol derivatives and their morpholine analogues have been synthesized and pharmacologically investigated in order to confirm some pharmacological observations made with the N-isopropyl-substituted compounds. In agreement with the previously obtained results, the weak alpha-adrenergic-stimulating activity and the potentiating effect on the responses to norepinephrine found in the open-chain compounds persist in their corresponding semirigid cyclic analogues. The results are discussed in the light of common knowledge of the structure-activity relationships of alpha-adrenergic drugs.

MeSH terms

  • Adrenergic alpha-Antagonists / pharmacology
  • Animals
  • Drug Interactions
  • In Vitro Techniques
  • Male
  • Molecular Conformation
  • Morpholines / chemical synthesis
  • Morpholines / pharmacology*
  • Muscle Contraction / drug effects
  • Muscle, Smooth / drug effects
  • Norepinephrine / pharmacology
  • Rats
  • Structure-Activity Relationship
  • Vas Deferens / drug effects

Substances

  • Adrenergic alpha-Antagonists
  • Morpholines
  • Norepinephrine