Synthesis, structure and antibacterial activity of novel 1-(5-substituted-3-substituted-4,5-dihydropyrazol-1-yl)ethanone oxime ester derivatives

Bioorg Med Chem. 2008 Apr 1;16(7):4075-82. doi: 10.1016/j.bmc.2008.01.035. Epub 2008 Jan 29.

Abstract

A series of novel 1-(5-substituted-3-substituted-4,5-dihydropyrazol-1-yl)ethanone oxime ester derivatives are synthesized. The results show that compounds 14 and 26c can strongly inhibit Staphylococcus aureus DNA gyrase and Escherichia coli DNA gyrase (with IC(50) of 0.25 and 0.125 microg/mL against S. aureus DNA gyrase, 0.125 and 0.25 microg/mL against E. coli DNA gyrase). On the basis of the biological results, structure-activity relationships are also discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Crystallography, X-Ray
  • DNA Gyrase / metabolism
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Escherichia coli / drug effects
  • Escherichia coli / enzymology
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Esters / pharmacology*
  • Ethane / chemistry*
  • Hydrogen / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Oximes / chemistry*
  • Pyrazoles / chemistry*
  • Staphylococcus aureus / drug effects
  • Staphylococcus aureus / enzymology
  • Structure-Activity Relationship
  • Topoisomerase II Inhibitors

Substances

  • Anti-Bacterial Agents
  • Enzyme Inhibitors
  • Esters
  • Oximes
  • Pyrazoles
  • Topoisomerase II Inhibitors
  • pyrazole
  • Hydrogen
  • DNA Gyrase
  • Ethane