Synthesis and antiviral activity of new pyrazole and thiazole derivatives

Eur J Med Chem. 2009 Sep;44(9):3746-53. doi: 10.1016/j.ejmech.2009.03.038. Epub 2009 Apr 5.

Abstract

New N-acetyl (5-8) and N-thiocarbamoyl (9-12) derivatives of 4,5-dihydropyrazole were synthesized starting from alpha,beta-unsaturated ketones under the effect of hydrazine hydrate and thiosemicarbazide, respectively. N-Thiocarbamoylpyrazole derivatives (9-12) were cyclized using either ethyl bromoacetate or phenacyl bromides to afford the novel pyrazolothiazol-4(5H)-ones (13-16) or pyrazolothiazoles (17-24). The antiviral activity for such novel compounds against a broad panel of viruses in different cell cultures revealed that N-acetyl 4,5-dihydropyrazole 7 was the only active one at subtoxic concentrations against vaccinia virus (Lederle strain) in HEL cell cultures with a 50% effective concentration (EC(50)) value of 7 microg/ml.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Antiviral Agents / toxicity
  • Chlorocebus aethiops
  • HeLa Cells
  • Humans
  • Microbial Sensitivity Tests
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology*
  • Pyrazoles / toxicity
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry*
  • Thiazoles / pharmacology*
  • Thiazoles / toxicity
  • Vero Cells
  • Viruses / drug effects

Substances

  • Antiviral Agents
  • Pyrazoles
  • Thiazoles
  • pyrazole