Improving anti-trypanosomal activity of 3-aminoquinoxaline-2-carbonitrile N1,N4-dioxide derivatives by complexation with vanadium

Bioorg Med Chem. 2006 Aug 15;14(16):5503-9. doi: 10.1016/j.bmc.2006.04.041. Epub 2006 May 18.

Abstract

New vanadium complexes of the type [V(IV)O(L)(2)], where L are 3-aminoquinoxaline-2-carbonitrile N(1),N(4)-dioxide derivatives, were prepared as an effort to obtain new anti-trypanosomal agents improving the bioactivity of the free ligands. Complexation to vanadium of the quinoxaline ligands leads to excellent antiprotozoal activity, similar to that of the reference drugs nifurtimox and benznidazole and in all cases higher than that of the corresponding free ligands. In addition, it is for the first time that the V((IV))O-quinoxaline complexes are reported as a family of anti-Trypanosoma cruzi agents. Finally, the anti-trypanosomal activity of these vanadium complexes could be explained on the basis of their lipophilicity and the electronic characteristics of the quinoxaline substituents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cells, Cultured
  • Cyclic N-Oxides / chemistry
  • Cyclic N-Oxides / pharmacology*
  • Ligands
  • Quinoxalines / chemistry
  • Quinoxalines / pharmacology*
  • Trypanocidal Agents / chemistry
  • Trypanocidal Agents / pharmacology*
  • Trypanosoma cruzi / drug effects*
  • Trypanosoma cruzi / metabolism
  • Vanadium / chemistry*

Substances

  • Cyclic N-Oxides
  • Ligands
  • Quinoxalines
  • Trypanocidal Agents
  • Vanadium