Synthesis, characterization, antiamoebic activity and toxicity of novel bisdioxazole derivatives

Eur J Med Chem. 2009 Nov;44(11):4747-51. doi: 10.1016/j.ejmech.2009.06.016. Epub 2009 Jun 21.

Abstract

Cyclization of benzene-1,4-dicarbaldehyde dioxime 1 with different aromatic aldehydes in inert atmosphere yielded the corresponding new bisdioxazoles 2-11. The structure of 2-11 was elucidated by spectral data. In vitro antiamoebic activity was performed against HM1:IMSS strain of Entamoeba histolytica. The results showed that the compounds 3 (IC(50)=1.22 microM), 4 (IC(50)=1.41 microM), 7 (IC(50)=1.05 microM) and 10 (IC(50)=1.01 microM) exhibited better antiamoebic activity than the standard drug metronidazole (IC(50)=1.80 microM). The compounds 3, 4, 7 and 10 were tested for toxicity by MTT assay on H9c2 cardiac myoblasts and the results showed that the compounds 3, 4, 7 and 10 offered remarkable viability of 96.2%, 83.5%, 82% and 89%, respectively at a concentration of 12.5 microg/ml.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amebicides / chemistry*
  • Amebicides / pharmacology*
  • Animals
  • Benzene / chemistry
  • Benzene / pharmacology
  • Cell Line
  • Cell Survival / drug effects
  • Entamoeba histolytica / drug effects*
  • Entamoebiasis / drug therapy*
  • Inhibitory Concentration 50
  • Myoblasts, Cardiac / cytology
  • Myoblasts, Cardiac / drug effects
  • Oxazoles / chemistry*
  • Oxazoles / pharmacology*
  • Parasitic Sensitivity Tests
  • Rats
  • Structure-Activity Relationship

Substances

  • Amebicides
  • Oxazoles
  • Benzene