Synthesis and antiviral activity of 4,4'-(arylmethylene)bis(1H-pyrazol-5-ols) against peste des petits ruminant virus (PPRV)

Bioorg Med Chem Lett. 2009 Aug 1;19(15):4501-3. doi: 10.1016/j.bmcl.2009.02.113. Epub 2009 Mar 3.

Abstract

An efficient and eco-friendly method for the synthesis of 4,4'-(arylmethylene)bis(1H-pyrazol-5-ols) has been accomplished by tandem Knoevenagel-Michael reaction of two equivalents of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one with various aromatic aldehydes catalyzed by ceric ammonium nitrate (CAN) in water. All the synthesized compounds 3a-j were evaluated for in vitro antiviral activity against peste des petits ruminant virus (PPRV). Compound 3i emerged as the most interesting compound in this series exhibiting excellent antiviral activity against PPRV and found to be more potent than the standard drug ribavirin used.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Cerium / chemistry
  • Chemistry, Organic / methods
  • Chemistry, Pharmaceutical / methods*
  • Chlorocebus aethiops
  • Drug Design
  • Models, Chemical
  • Peste-des-Petits-Ruminants / drug therapy*
  • Peste-des-petits-ruminants virus / metabolism*
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacology
  • Ribavirin / pharmacology
  • Vero Cells
  • Water / chemistry

Substances

  • Antiviral Agents
  • Pyrazoles
  • Water
  • Cerium
  • Ribavirin
  • ceric ammonium nitrate