Cu(II) Complexes of 4-[(1 E)- N-{2-[(Z)-Benzylidene-amino]ethyl}ethanimidoyl]benzene-1,3-diol Schiff Base: Synthesis, Spectroscopic, In-Vitro Antioxidant, Antifungal and Antibacterial Studies

Molecules. 2018 Jun 29;23(7):1581. doi: 10.3390/molecules23071581.

Abstract

The current study reports the synthesis of copper complexes of a tridentate Schiff base ligand. The compounds of the type [Cu(L)X]∙n(H₂O) (where L = tridentate ONN Schiff base ligand, X = Cl, Br, SCN, NO₃, CH₃COO), were characterized on the basis of elemental analyses, FT-IR, UV-vis, molar conductance, ¹H-NMR, XRD and thermal analyses. The spectra revealed that the Schiff base ligand acts as a tridentate ligand through two azomethine nitrogen atoms and a phenolic oxygen atom. The molar conductance measurements of the complexes in DMF correspond to non-electrolytic nature. TGA and DTA studies results gave insight into the dehydration, thermal stability, and thermal decomposition. Square-planar geometry has been assigned to the prepared complexes as indicated by the electronic spectral measurements. Cu(II) compounds showed antiradical potential against DPPH and ABTS radicals. The antimicrobial potential of the Schiff base ligand and its Cu(II) complexes were evaluated by the rapid p-iodonitrotetrazolium chloride (INT) colorimetric assay against some selected bacteria strains: Staphylococcus aureus and Enterococcus faecalis (Gram +ve); Klebsiella pneumoniae and Pseudomonas aeruginosa (Gram −ve), and fungi (Candida albicans and Cryptococcus neoformans). The compounds showed a broad spectrum of antibacterial and antifungal activities, with MIC values ranging from 48.83 to 3125 μg/mL.

Keywords: 2′,4′-dihydroxyacetophenone; ABTS assay; DPPH assay; antimicrobial activity; copper(II) complexes; unsymmetrical Schiff base.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology
  • Bacteria / drug effects
  • Candida albicans / drug effects
  • Chemistry Techniques, Synthetic
  • Copper / chemistry*
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Schiff Bases / chemical synthesis
  • Schiff Bases / chemistry*
  • Schiff Bases / pharmacology
  • Spectroscopy, Fourier Transform Infrared
  • Spectrum Analysis
  • X-Ray Diffraction

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Antioxidants
  • Ligands
  • Schiff Bases
  • Copper