N-Monosubstituted urethanes of 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclo [2.2.2] octan-5-trans-ols with hypotensive and other activities

Farmaco Sci. 1982 Apr;37(4):223-39. doi: 10.1002/chin.198239245.

Abstract

The synthesis of three series of N-monosubstituted urethanes of 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclo [2.2.2] octan-5-transols (IV), (V) and (VI) (dialkylamino = pyrrolidino, piperidino, morpholino) by reaction of the corresponding aminoalcohols with alkyl or aryl isocyanates, is described. A number of compounds (IV) and (V) showed remarkable hypotensive and bradycardic activity in rats, whereas (IV c) showed infiltration anesthesia and (IV n) antiarrhythmic activity in mice comparable to those of lidocaine. Antiacetylcholine activity in vitro is also reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholine / antagonists & inhibitors
  • Amino Alcohols / chemical synthesis*
  • Amino Alcohols / pharmacology
  • Anesthetics / chemical synthesis
  • Animals
  • Anti-Arrhythmia Agents / chemical synthesis
  • Antihypertensive Agents / chemical synthesis*
  • Chemical Phenomena
  • Chemistry
  • Heart Rate / drug effects
  • Mice
  • Urethane / analogs & derivatives
  • Urethane / chemical synthesis
  • Urethane / pharmacology

Substances

  • Amino Alcohols
  • Anesthetics
  • Anti-Arrhythmia Agents
  • Antihypertensive Agents
  • Urethane
  • Acetylcholine