Facile solid state ball milling as a green strategy to prepare 2-(2,4-dichlorophenoxy)-N'-(2-hydroxybenzylidene)acetohydrazide complexes

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Nov 11:132:846-53. doi: 10.1016/j.saa.2014.05.062. Epub 2014 Jun 5.

Abstract

2-(2,4-Dichlorophenoxy)-N'-(2-hydroxybenzylidene)acetohydrazide (H2L) complexes were prepared by ball milling involving the reaction of ligand with Ni(II), Co(II), Cu(II) and VO(II) salts (mechanochemical syntheses). The compounds were elucidated by elemental analysis, spectroscopy (1H NMR, IR, UV-visible, MS spectra), and physical measurements (magnetic susceptibility and molar conductance). IR spectra suggested that the H2L behaved as a monodentate and/or bidentate ligand coordinating via azomethine nitrogen and/or deprotonated enolized carbonyl oxygen. The electronic spectra of the complexes and their magnetic moments provided information about geometries. The antimicrobial activities of the ligand and its complexes were studied against gram positive bacteria; Staphylococcus aureus, gram-negative bacteria; Escherichia coli and pathogenic fungi; Candida albicans by using minimum inhibition concentrations method (MIC). Also, the antioxidant (ABTS-derived free radical method) and cytotoxic (in vitro Ehrlich Ascites) activities of the isolated compounds were evaluated.

Keywords: Antimicrobial; Antioxidant; Ball milling; Cytotoxic; Hydrazone complexes.

MeSH terms

  • Anti-Infective Agents / pharmacology
  • Antioxidants / pharmacology
  • Bacteria / drug effects
  • Benzothiazoles / pharmacology
  • Cell Death / drug effects
  • Cell Proliferation / drug effects
  • Coordination Complexes / chemical synthesis*
  • Coordination Complexes / chemistry
  • Coordination Complexes / pharmacology
  • Electrons
  • Fungi / drug effects
  • Green Chemistry Technology / methods*
  • Hep G2 Cells
  • Humans
  • Hydrazones / chemical synthesis*
  • Hydrazones / chemistry
  • Hydrazones / pharmacology
  • Inhibitory Concentration 50
  • Ligands
  • Magnetic Phenomena
  • Microbial Sensitivity Tests
  • Proton Magnetic Resonance Spectroscopy
  • Solvents
  • Spectrophotometry, Infrared
  • Sulfonic Acids / pharmacology

Substances

  • Anti-Infective Agents
  • Antioxidants
  • Benzothiazoles
  • Coordination Complexes
  • Hydrazones
  • Ligands
  • Solvents
  • Sulfonic Acids
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid