Novel arylpyrazino[2,3-c][1,2,6]thiadiazine 2,2-dioxides as inhibitors of platelet aggregation. 1. Synthesis and pharmacological evaluation

J Med Chem. 1999 May 20;42(10):1698-704. doi: 10.1021/jm981103j.

Abstract

A series of N-1-substituted derivatives of pyrazino[2,3-c][1,2, 6]thiadiazine 2,2-dioxides bearing aryl groups at the pyrazino moiety have been prepared. The synthesis involves ring formation between the diaminothiadiazine and suitable dicarbonyl compounds and subsequent introduction of the substituent at N-1. The compounds have been tested in vitro, as inhibitors of rabbit and human platelet aggregation, and ex vivo against rat platelet aggregation induced by arachidonic acid, ADP, collagen, U46619, and I-BOP. The results obtained indicate that some pyrazino[2,3-c][1,2, 6]thiadiazine derivatives show significant platelet aggregation inhibition similar to other antithrombotic agents and that the antiplatelet properties may be mediated by interference with the arachidonic acid pathway.

MeSH terms

  • Animals
  • Cyclic S-Oxides / chemical synthesis*
  • Cyclic S-Oxides / chemistry
  • Cyclic S-Oxides / pharmacology
  • Humans
  • In Vitro Techniques
  • Male
  • Platelet Aggregation Inhibitors / chemical synthesis*
  • Platelet Aggregation Inhibitors / chemistry
  • Platelet Aggregation Inhibitors / pharmacology
  • Rabbits
  • Rats
  • Rats, Wistar
  • Structure-Activity Relationship
  • Thiadiazines / chemical synthesis*
  • Thiadiazines / chemistry
  • Thiadiazines / pharmacology

Substances

  • Cyclic S-Oxides
  • Platelet Aggregation Inhibitors
  • Thiadiazines