Design, Synthesis, and Biological Activities of Novel Pyrazole Oxime Compounds Containing a Substituted Pyridyl Moiety

Molecules. 2017 May 25;22(6):878. doi: 10.3390/molecules22060878.

Abstract

In this paper, in order to find novel biologically active pyrazole oximes, a series of pyrazole oxime compounds bearing a substituted pyridyl unit were prepared. Bioassays showed that some target compounds were found to have good acaricidal activity against Tetranychus cinnabarinus at a concentration of 500 μg/mL, compound 9q especially displayed potent acaricidal activity against T. cinnabarinus when the concentration was reduced to 100 μg/mL. Interestingly, most target compounds possessed excellent insecticidal activities against Oriental armyworm at 500 μg/mL. Moreover, some compounds were active against Aphis medicaginis and Nilaparvata lugens at 500 μg/mL. Additionally, compounds 9b, 9g, 9l, 9p, 9q, 9r, 9s, 9t, 9u, and 9v displayed significant antiproliferative activities against HepG2 cells with IC50 values of 1.53-17.27 μM, better than that of the control 5-fluorouracil (IC50 = 35.67 μM).

Keywords: biological activity; pyrazole oxime; pyridyl; synthesis.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Design*
  • Humans
  • Insecticides / chemical synthesis
  • Insecticides / chemistry
  • Insecticides / pharmacology
  • Molecular Structure
  • Oximes / chemical synthesis
  • Oximes / chemistry*
  • Oximes / pharmacology*
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology*
  • Pyridines* / chemistry
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Insecticides
  • Oximes
  • Pyrazoles
  • Pyridines
  • pyrazole