New amide derivatives of quinoxaline 1,4-di-N-oxide with leishmanicidal and antiplasmodial activities

Molecules. 2013 Apr 22;18(4):4718-27. doi: 10.3390/molecules18044718.

Abstract

Malaria and leishmaniasis are two of the World's most important tropical parasitic diseases. Continuing with our efforts to identify new compounds active against malaria and leishmaniasis, twelve new 1,4-di-N-oxide quinoxaline derivatives were synthesized and evaluated for their in vitro antimalarial and antileishmanial activity against Plasmodium falciparum FCR-3 strain, Leishmania infantum and Leishmania amazonensis. Their toxicity against VERO cells (normal monkey kidney cells) was also assessed. The results obtained indicate that a cyclopentyl derivative had the best antiplasmodial activity (2.9 µM), while a cyclohexyl derivative (2.5 µM) showed the best activity against L. amazonensis, and a 3-chloropropyl derivative (0.7 µM) showed the best results against L. infantum. All these compounds also have a Cl substituent in the R⁷ position.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Animals
  • Antimalarials / chemistry
  • Antimalarials / pharmacology
  • Antimalarials / toxicity
  • Antiparasitic Agents / chemistry
  • Antiparasitic Agents / pharmacology*
  • Antiparasitic Agents / toxicity
  • Chlorocebus aethiops
  • Humans
  • Inhibitory Concentration 50
  • Leishmania / drug effects*
  • Leishmania infantum / drug effects
  • Oxides / chemistry
  • Parasitic Sensitivity Tests
  • Plasmodium / drug effects*
  • Plasmodium falciparum / drug effects
  • Quinoxalines / chemistry
  • Quinoxalines / pharmacology*
  • Quinoxalines / toxicity
  • Structure-Activity Relationship
  • Vero Cells

Substances

  • Amides
  • Antimalarials
  • Antiparasitic Agents
  • Oxides
  • Quinoxalines