Studies on annelated 1,4-benzothiazines and 1,5-benzothiazepines. I. Synthesis of 4H-s-triazolo[3,4-c]-1,4-benzothiazine and derivatives with potential CNS activity

Farmaco Sci. 1985 Apr;40(4):221-36.

Abstract

As a part of a program toward the synthesis and the pharmacological studies on annelated 1,4-benzothiazines and 1,5-benzothiazepines, a number of 4H-s-triazolo[3,4-c]-1,4-benzothiazine derivatives were prepared and tested for their CNS activity. The syntheses of the new tricyclic compounds (VII) were performed via the 2H-1,4-benzothiazine-3(4H)-thiones (II) which were obtained by Lawesson's thiation of lactams (I). Compounds (II) and their S-methyl-thioethers (III), quantitatively obtained by PTC method, were reacted with acylhydrazines to give the title compounds. Some triazolobenzothiazines (VII) were also prepared from 3-hydrazinoderivatives (IV) by cyclization with either an aliphatic acid or the corresponding orthoesther.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anticonvulsants / chemical synthesis
  • Central Nervous System Depressants / chemical synthesis*
  • Chemical Phenomena
  • Chemistry
  • Lethal Dose 50
  • Male
  • Mice
  • Motor Activity / drug effects
  • Thiazines / chemical synthesis*
  • Thiazines / pharmacology
  • Thiazines / toxicity
  • Triazoles / chemical synthesis*
  • Triazoles / pharmacology
  • Triazoles / toxicity

Substances

  • Anticonvulsants
  • Central Nervous System Depressants
  • Thiazines
  • Triazoles