Discovery and Optimization of 5-Amino-1,2,3-triazole-4-carboxamide Series against Trypanosoma cruzi

J Med Chem. 2017 Sep 14;60(17):7284-7299. doi: 10.1021/acs.jmedchem.7b00463. Epub 2017 Aug 27.

Abstract

Chagas' disease, caused by the protozoan parasite Trypanosoma cruzi, is the most common cause of cardiac-related deaths in endemic regions of Latin America. There is an urgent need for new safer treatments because current standard therapeutic options, benznidazole and nifurtimox, have significant side effects and are only effective in the acute phase of the infection with limited efficacy in the chronic phase. Phenotypic high content screening against the intracellular parasite in infected VERO cells was used to identify a novel hit series of 5-amino-1,2,3-triazole-4-carboxamides (ATC). Optimization of the ATC series gave improvements in potency, aqueous solubility, and metabolic stability, which combined to give significant improvements in oral exposure. Mitigation of a potential Ames and hERG liability ultimately led to two promising compounds, one of which demonstrated significant suppression of parasite burden in a mouse model of Chagas' disease.

MeSH terms

  • Amination
  • Animals
  • Chagas Disease / drug therapy*
  • Chagas Disease / parasitology
  • Chlorocebus aethiops
  • Drug Discovery
  • Female
  • Humans
  • Mice
  • Structure-Activity Relationship
  • Triazoles / chemistry*
  • Triazoles / pharmacokinetics
  • Triazoles / pharmacology
  • Triazoles / therapeutic use*
  • Trypanocidal Agents / chemistry*
  • Trypanocidal Agents / pharmacokinetics
  • Trypanocidal Agents / pharmacology
  • Trypanocidal Agents / therapeutic use*
  • Trypanosoma cruzi / drug effects*
  • Vero Cells

Substances

  • Triazoles
  • Trypanocidal Agents