Synthesis and in vitro antiprotozoal activities of 5-phenyliminobenzo[a]phenoxazine derivatives

Bioorg Med Chem Lett. 2011 Oct 1;21(19):5804-7. doi: 10.1016/j.bmcl.2011.07.112. Epub 2011 Aug 5.

Abstract

A series of 5-phenyliminobenzo[a]phenoxazine derivatives were synthesized. The in vitro antiprotozoal activities were evaluated against Plasmodium falciparum K1, Trypanosoma cruzi, Leishmania donovani and Trypanosoma brucei rhodesiense. N,N-Diethyl-5-((4-methoxyphenyl)imino)-5H-benzo[a]phenoxazin-9-amine shows IC(50)=0.040 μmol L(-1) with a selective index of 1425 against Plasmodium falciparum K1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / pharmacology*
  • Antimalarials / toxicity
  • Antiprotozoal Agents / chemical synthesis*
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / pharmacology*
  • Antiprotozoal Agents / toxicity
  • Drug Design*
  • Inhibitory Concentration 50
  • Leishmania donovani / drug effects
  • Malaria / drug therapy
  • Malaria / epidemiology
  • Models, Chemical
  • Molecular Structure
  • Myoblasts
  • Oxazines / chemical synthesis*
  • Oxazines / chemistry
  • Oxazines / pharmacology*
  • Oxazines / toxicity
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects
  • Pyridinium Compounds / chemistry
  • Rats
  • Structure-Activity Relationship
  • Thiazoles / chemistry
  • Trypanocidal Agents / chemical synthesis
  • Trypanocidal Agents / chemistry
  • Trypanocidal Agents / pharmacology
  • Trypanocidal Agents / toxicity
  • Trypanosoma brucei rhodesiense / drug effects
  • Trypanosoma cruzi / drug effects

Substances

  • Antimalarials
  • Antiprotozoal Agents
  • N,N-diethyl-5-((4-methoxyphenyl)imino)-5H-benzo(a)phenoxazin-9-amine
  • Oxazines
  • Pyridinium Compounds
  • Thiazoles
  • Trypanocidal Agents
  • rhodacyanine
  • phenoxazine