Synthesis and beta-adrenergic blocking activity of new aliphatic oxime ethers

J Med Chem. 1980 Jun;23(6):620-4. doi: 10.1021/jm00180a007.

Abstract

New beta-adrenergic blocking agents, most of which do not contain an aromatic nucleus, were synthesized. They were derived either from alkylamino-aliphatic oxime ethers or alkylamino-aliphatic ethers. Most active among these are O-[3-(tert-butylamino)-2-hydroxypropyl]acetoxime (8; trachea pA2 = 7.65) and 1-isobutoxy-3-(tert-butylamino)-2-propanol (15; trachea pA2 = 7.49), both of which displayed bronchoselectivity (beta 2/beta 1 ratio approximately 15). The role and importance of the aromatic nucleus in this class of compounds are discussed.

MeSH terms

  • Adrenergic beta-Antagonists / chemical synthesis*
  • Animals
  • Ethers / chemical synthesis
  • Ethers / pharmacology
  • Guinea Pigs
  • Heart Rate / drug effects
  • In Vitro Techniques
  • Muscle Contraction / drug effects
  • Muscle, Smooth / drug effects
  • Oximes / chemical synthesis*
  • Oximes / pharmacology
  • Structure-Activity Relationship
  • Trachea / drug effects

Substances

  • Adrenergic beta-Antagonists
  • Ethers
  • Oximes