Synthesis and evaluation of monoamidoxime derivatives: toward new antileishmanial compounds

Eur J Med Chem. 2011 Jul;46(7):2984-91. doi: 10.1016/j.ejmech.2011.04.026. Epub 2011 Apr 15.

Abstract

A new series of monoamidoxime derivatives was synthesized using manganese(III) acetate by microwave irradiation. Several amidoximes (27-31, 33, 38) showed valuable in vitro activities toward Leishmania donovani promastigotes, exhibiting IC(50) values between 5.21 and 7.89 μM. In parallel, the cytotoxicity of these compounds was evaluated on murine J774A.1 cells, revealing the corresponding selectivity index (SI). Among the 13 tested compounds, 4 monoamidoximes (27-30) exhibited an SI more than 20 times better than pentamidine. Moreover, monoamidoxime 28 (4-[5-Benzyl-3-(4-fluorophenylsulfonyl)-5-methyl-4,5-dihydrofuran-2-yl]-N'-hydroxybenzimidamide) is 40 times more selective than pentamidine, and 1.6 times more than amphotericin B, used as reference drug compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry
  • Amphotericin B / pharmacology
  • Animals
  • Antiprotozoal Agents / chemical synthesis*
  • Antiprotozoal Agents / pharmacology
  • Cell Line
  • Inhibitory Concentration 50
  • Leishmania donovani / drug effects*
  • Leishmania donovani / growth & development
  • Life Cycle Stages / drug effects*
  • Macrophages / drug effects
  • Macrophages / parasitology
  • Mice
  • Microwaves
  • Organometallic Compounds / chemistry
  • Oximes / chemical synthesis*
  • Oximes / pharmacology
  • Pentamidine / pharmacology
  • Structure-Activity Relationship

Substances

  • Acetates
  • Antiprotozoal Agents
  • Organometallic Compounds
  • Oximes
  • manganese(III) acetate dihydrate
  • Pentamidine
  • Amphotericin B