Design and synthesis of a series of melamine-based nitroheterocycles with activity against Trypanosomatid parasites

J Med Chem. 2005 Aug 25;48(17):5570-9. doi: 10.1021/jm050177+.

Abstract

The parasites that give rise to human African trypanosomiasis (HAT) are auxotrophs for various nutrients from the human host, including purines. They have specialist nucleoside transporters to import these metabolites. In addition to uptake of purine nucleobases and purine nucleosides, one of these transporters, the P2 transporter, can carry melamine derivatives; these derivatives are not substrates for the corresponding mammalian transporters. In this paper, we report the coupling of the melamine moiety to selected nitro heterocycles with the aim of selectively delivering these compounds to the parasites. Some compounds prepared have similar in vitro trypanocidal activities as melarsoprol, the principal drug used against late-stage HAT, with 50% growth inhibitory concentrations in the submicromolar range. Selected compounds were also evaluated in vivo in rodent models infected with Trypanosoma brucei brucei and T. brucei rhodesiense and showed pronounced activity and in two cases were curative without overt signs of toxicity. Compounds were also tested against other trypanosomatid pathogens, Leishmania donovani and Trypanosoma cruzi, and significant activity in vitro was noted for T. cruzi against which various nitro heterocycles are already registered for use.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Female
  • Furaldehyde / chemical synthesis
  • Furaldehyde / chemistry
  • Furaldehyde / pharmacology
  • Hydrazones / chemical synthesis
  • Hydrazones / chemistry
  • Hydrazones / pharmacology
  • Leishmania donovani / drug effects
  • Mice
  • Nitrofurans / chemical synthesis
  • Nitrofurans / chemistry
  • Nitrofurans / pharmacology
  • Nucleoside Transport Proteins / metabolism
  • Rats
  • Thiophenes / chemical synthesis
  • Thiophenes / chemistry
  • Thiophenes / pharmacology
  • Triazines / chemical synthesis*
  • Triazines / chemistry
  • Triazines / pharmacology
  • Trypanocidal Agents / chemical synthesis*
  • Trypanocidal Agents / chemistry
  • Trypanocidal Agents / pharmacology
  • Trypanosoma brucei brucei / drug effects
  • Trypanosoma brucei rhodesiense / drug effects
  • Trypanosoma cruzi / drug effects
  • Trypanosomiasis, African / drug therapy

Substances

  • Hydrazones
  • Nitrofurans
  • Nucleoside Transport Proteins
  • P2 transporter, Trypanosoma brucei
  • Thiophenes
  • Triazines
  • Trypanocidal Agents
  • Furaldehyde
  • melamine