Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus

Eur J Med Chem. 2020 Mar 15:190:112100. doi: 10.1016/j.ejmech.2020.112100. Epub 2020 Jan 25.

Abstract

Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78-22.4 μM) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization.

Keywords: Anthelmintic; Drug discovery; Haemonchus contortus; Pyrrolidine-oxadiazoles; Structure-activity relationship.

MeSH terms

  • Animals
  • Anthelmintics / chemical synthesis
  • Anthelmintics / pharmacology*
  • Anthelmintics / toxicity
  • Cell Line
  • Haemonchus / drug effects*
  • Humans
  • Molecular Structure
  • Motor Activity / drug effects
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / pharmacology*
  • Oxadiazoles / toxicity
  • Parasitic Sensitivity Tests
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / pharmacology*
  • Pyrrolidines / toxicity
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Anthelmintics
  • Oxadiazoles
  • Pyrrolidines