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Molecules 2015, 20(6), 9788-9802; doi:10.3390/molecules20069788

Synthesis, Characterization and Biological Studies of Metal(II) Complexes of (3E)-3-[(2-{(E)-[1-(2,4-Dihydroxyphenyl) ethylidene]amino}ethyl)imino]-1-phenylbutan-1-one Schiff Base

Department of Chemistry, Faculty of Science and Agriculture, University of Fort Hare, P.B. X1314, Alice 5700, South Africa
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Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 3 April 2015 / Accepted: 15 May 2015 / Published: 27 May 2015
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Co(II), Ni(II), Zn(II) and Cu(II) complexes of (3E)-3-[(2-{(E)-[1-(2,4-dihydroxyphenyl)ethylidene]amino}ethyl)imino]-1-phenylbutan-1-one (DEPH2) derived from ethylenediamine, 2′,4′-dihydroxyacetophenone and 1-phenylbutane-1,3-dione have been synthesized and characterized by elemental analysis, FTIR, UV-Visible spectroscopy, and screened to establish their potential as antibacterial agents, antioxidants and DPPH radical scavengers. The FTIR spectra showed that the ligand behaves as a dibasic tetradentate ligand with the dioxygen-dinitrogen donor atom system oriented towards the central metal ion. The analytical and spectroscopic data suggest a square planar geometry for Cu(II) and Ni(II) complexes and an octahedral geometry for the Co(II) complex. The ligand and their metal complexes were screened for antibacterial activity against Gram (+) and Gram (−) bacteria by the agar well diffusion method. In addition, the antioxidant activities of the complexes were also investigated through their scavenging effect on DPPH and ABTS radicals. The obtained IC50 value of the DPPH activity for the copper complex (2.08 ± 0.47 µM) and that of the ABTS activity for the copper complex (IC50 = 2.11 + 1.69 µM) were higher than the values obtained for the other compounds. View Full-Text
Keywords: 2′,4′-dihydroxyacetophenone; unsymmetrical tetradentate Schiff base; antibacterial activity; DPPH; ABTS 2′,4′-dihydroxyacetophenone; unsymmetrical tetradentate Schiff base; antibacterial activity; DPPH; ABTS
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Ejidike, I.P.; Ajibade, P.A. Synthesis, Characterization and Biological Studies of Metal(II) Complexes of (3E)-3-[(2-{(E)-[1-(2,4-Dihydroxyphenyl) ethylidene]amino}ethyl)imino]-1-phenylbutan-1-one Schiff Base. Molecules 2015, 20, 9788-9802.

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