Synthesis, Structural Characterization and Biological Activity of Novel Cyclohexane-1,3-dione Ligands and Their Metal Complexes

Molecules. 2015 May 21;20(5):9309-25. doi: 10.3390/molecules20059309.

Abstract

Some new Zn(II) and Cu(II) complexes [Cu(L1)(OAc)2]∙H2O, [Cu(L1)(NO3)H2O]∙NO3∙3.5H2O, [Zn(L1)(NO3)2]∙4.5H2O, [Zn(L1)(OAc)2(H2O)2]∙3H2O, [Cu2(L2)(OAc)4]∙2H2O∙2DMF, [Cu(L2)2]∙2NO3∙1.5DMF∙H2O, [Zn(L2)2(NO3)2]∙DMF and [Zn2(L2)(OAc)4(H2O)4]∙5H2O; L1 = 2-[2-(2-methoxyphenyl)hydrazono]cyclohexane-1,3-dione and L2 = 2-[2-(3-nitrophenyl)hydrazono]cyclohexane-1,3-dione were synthesized and characterized by IR, 1H-NMR,13C-NMR and ultraviolet (UV-Vis.) spectroscopy, elemental analysis, magnetic susceptibility, mass spectrometry and thermogravimetry-differential thermal analysis (TGA-DTA). The synthesized ligands and their complexes were tested for antibacterial activity against Escherichia coli ATCC 25922, Enterococcus faecalis ATCC 29212, Staphylococcus aureus ATCC 25923, and Salmonella typhimurium CCM 583. Some of complexes showed medium-level antibacterial activity against the test bacteria compared with ampicillin.

Keywords: antibacterial activity; cyclohexane-1,3-dione; mass spectra; metal complexes; spectroscopic characterization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology*
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / pharmacology*
  • Copper / chemistry
  • Cyclohexanones / chemical synthesis
  • Cyclohexanones / pharmacology*
  • Enterococcus faecalis / drug effects
  • Escherichia coli / drug effects
  • Hydrazones / chemical synthesis
  • Hydrazones / pharmacology*
  • Ligands
  • Mass Spectrometry
  • Microbial Sensitivity Tests
  • Nuclear Magnetic Resonance, Biomolecular
  • Salmonella typhimurium / drug effects
  • Staphylococcus aureus / drug effects
  • Zinc / chemistry

Substances

  • 2-(2-(2-methoxyphenyl)hydrazono)cyclohexane-1,3-dione
  • 2-(2-(3-nitrophenyl)hydrazono)cyclohexane-1,3-dione
  • Anti-Bacterial Agents
  • Coordination Complexes
  • Cyclohexanones
  • Hydrazones
  • Ligands
  • cyclohexanone
  • Copper
  • Zinc