Synthesis and antiviral activity of novel pyrazole derivatives containing oxime esters group

Bioorg Med Chem. 2008 Nov 15;16(22):9699-707. doi: 10.1016/j.bmc.2008.09.070. Epub 2008 Oct 2.

Abstract

Fourteen title compounds, 1-substituted-5-substitutedphenylthio-4-pyrazolaldoxime ester derivatives 4a-4n, were synthesized from the starting material 1-substitutedphenyl-3-methyl-5-substitutedphenylthio-4-pyrazolaldoximes 3 by treatment with acyl chloride. The synthesized compounds were characterized by physical constants, and the structures of the title compounds were further confirmed by IR, 1H NMR, 13C NMR and elemental analysis. The bioassay results showed that title compounds possessed weak to good anti-TMV bioactivity with 4l showing significant enhancement of disease resistance in tobacco leaves with high affinity for TMV CP.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Esters / chemical synthesis
  • Esters / chemistry
  • Esters / pharmacology
  • Nicotiana / metabolism
  • Nicotiana / virology
  • Oximes / chemical synthesis
  • Oximes / chemistry
  • Oximes / pharmacology*
  • Plant Leaves / metabolism
  • Plant Leaves / virology
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • RNA / analysis
  • RNA / genetics
  • Reverse Transcriptase Polymerase Chain Reaction
  • Tobacco Mosaic Virus / drug effects

Substances

  • Antiviral Agents
  • Enzyme Inhibitors
  • Esters
  • Oximes
  • Pyrazoles
  • RNA