Antileishmanial bis-arylimidamides: DB766 analogs modified in the linker region and bis-arylimidamide structure-activity relationships

Bioorg Med Chem Lett. 2012 Nov 15;22(22):6806-10. doi: 10.1016/j.bmcl.2012.06.037. Epub 2012 Jun 16.

Abstract

Analogs of the lead antileishmanial bis-arylimidamide DB766 were prepared that possess unsymmetrical substitutions on the diphenylfuran linker, and an additional compound was synthesized that contains isopropoxy groups meta to the central furan. These agents all displayed nanomolar in vitro potency against intracellular Leishmania with selectivity indexes >100 compared to J774 macrophages. While the unsymmetrical analogs were toxic to mice when given ip at 30 mg/kg/day, the compound bearing the meta isopropoxy groups was well tolerated by mice and showed activity in a murine model of visceral leishmaniasis when administered ip at 30 mg/kg/day for five days.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidines / chemistry*
  • Amidines / pharmacology
  • Amidines / therapeutic use
  • Animals
  • Antiprotozoal Agents / chemistry*
  • Antiprotozoal Agents / pharmacology
  • Antiprotozoal Agents / therapeutic use
  • Furans / chemistry*
  • Furans / pharmacology
  • Furans / therapeutic use
  • Leishmania / drug effects
  • Leishmaniasis, Visceral / drug therapy
  • Macrophages / drug effects
  • Mice
  • Mice, Inbred BALB C
  • Structure-Activity Relationship

Substances

  • 2,5-bis(2-(2-propoxy)-4-(2-pyridylimino)aminophenyl)furan
  • Amidines
  • Antiprotozoal Agents
  • Furans