omega-Dialkylaminoalkyl esters of N-phenyl aminethiocarboximidic acids with local anesthetic and other activities

Farmaco. 1992 Oct;47(10):1263-83.

Abstract

A series of omega-dialkylaminoalkyl esters of N-phenyl aminethiocarboximidic acids was prepared by reaction of N-phenyl 1-pyrrolidine, 1-piperidine, 4-morpholine, 1,2,3,4-tetrahydro-1-quinoline, 1,2,3,4-tetrahydro-2-isoquinoline, 10-phenothiazine, N-phenyl-2-pyridylamine and N-benzyl-2-pyridylamine-carbothioamides (prepared in situ from the appropriate secondary amine and phenyl isothiocyanate) with a number of omega-chloroalkyldialkylamines in anhydrous DMF or THF solution in the presence of sodium hydride. Good yields of the above esters were obtained provided that sodium hydride was added initially or after the formation of 3,3-disubstituted 1-phenylthiourea, according to the nature of the secondary amine. Some esters showed in mice local anesthetic activity comparable with that of lidocaine, as well as moderate hypoglycemic, antiarrhythmic, analgesic, antiacetylcholine, H1-antithistamine and platelet antiaggregating activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholine / antagonists & inhibitors
  • Analgesics / chemical synthesis
  • Analgesics / pharmacology
  • Anesthetics, Local / chemical synthesis*
  • Anesthetics, Local / pharmacology
  • Animals
  • Anti-Arrhythmia Agents / chemical synthesis
  • Anti-Arrhythmia Agents / pharmacology
  • Histamine H1 Antagonists / chemical synthesis
  • Histamine H1 Antagonists / pharmacology
  • Humans
  • Hypoglycemic Agents / chemical synthesis
  • Hypoglycemic Agents / pharmacology
  • Imidoesters / chemical synthesis*
  • Imidoesters / pharmacology
  • In Vitro Techniques
  • Mice
  • Platelet Aggregation Inhibitors / chemical synthesis
  • Platelet Aggregation Inhibitors / pharmacology
  • Rats

Substances

  • Analgesics
  • Anesthetics, Local
  • Anti-Arrhythmia Agents
  • Histamine H1 Antagonists
  • Hypoglycemic Agents
  • Imidoesters
  • Platelet Aggregation Inhibitors
  • Acetylcholine