Synthesis and potential anthelmintic activity of methyl-5-(4-salicyloyl-piperazin-1-yl)-benzimidazole-2-carbamates

Arzneimittelforschung. 1993 Jun;43(6):689-94.

Abstract

A series of methyl-5-(4-salicyloyl-piperazin-1-yl)-benzimidazole-2-carba mates (IX) has been prepared. 5-(4-Salicyloyl-piperazin-1-yl)-2-nitro anilines (VII) have been synthesized starting from 5-piperazino-2-nitro anilines and salicyloyl chlorides. Catalytic reduction of VII with Pd/C, followed by treatment with 1,3-dicarbomethoxy-S-methyl isothiourea, yielded the corresponding carbamates (IX), the anthelmintic activity of which was studied. Compound IXa significantly reduced the numbers of preadults, adults and encysted T. spiralis larvae in experimental mice.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthelmintics / chemical synthesis*
  • Anthelmintics / pharmacology
  • Anthelmintics / therapeutic use
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / pharmacology
  • Benzimidazoles / therapeutic use
  • Caenorhabditis elegans / drug effects
  • Caenorhabditis elegans / growth & development
  • Carbamates / chemical synthesis*
  • Carbamates / pharmacology
  • Carbamates / therapeutic use
  • Mice
  • Mice, Inbred Strains
  • Muscles / parasitology
  • Trichinella spiralis / drug effects
  • Trichinella spiralis / growth & development
  • Trichinellosis / drug therapy
  • Trichinellosis / parasitology

Substances

  • Anthelmintics
  • Benzimidazoles
  • Carbamates