Syntheses, characterization, and biological activity of novel mono- and binuclear transition metal complexes with a hydrazone Schiff base derived from a coumarin derivative and oxalyldihydrazine

Abstract

Abstract: A hydrazone Schiff base ligand was synthesized by the condensation of 3-formyl-4-hydroxycoumarin and oxalyldihydrazide in the molar ratio 2:1. The Schiff base ligand acts as a mono-, bi-, tri- or even tetradentate ligand with metal cations in the molar ratios 1:1 or 2:1 (M:L) to yield either mono- or binuclear complexes as keto or enol isomers, where M = Co(II), Ni(II), Cu(II), VO(IV), and Fe(III). The ligand and its metal complexes were characterized by elemental analyses, IR, ¹H NMR, mass, and UV-Vis spectroscopy. Furthermore, the magnetic moments were calculated from the measured electric conductivities of the complexes. According to the received data, the dihydrazone ligand contains one or two units of ONO domains and can bind to the metal ions via the azomethine nitrogen, the carbonyl oxygen atoms, and/or the phenolic oxygen atoms. Electronic spectra and the magnetic moments of all complexes show that the complexes' geometries are either octahedral, tetrahedral, square planar, or square pyramidal. Cyclic voltammograms of the mononuclear Co(II) and Ni(II) complexes show quasi-reversible peaks. Tests against two pathogenic bacteria as Gram-positive and Gram-negative bacteria for both, the Schiff base ligand and its metal complexes were carried out. In addition, also one kind of fungi was tested. The synthesized complexes demonstrate mild antibacterial and antifungal activities against these organisms.

Keywords: 3-Formyl-4-hydroxycoumarin derivative; Antibacterial and antifungal activity; Cyclic voltammetry; Mono- and binuclear complexes.

Fig. 1

Electronic absorption spectrum of 1 in a DMF solution (10⁻³ M)

Fig. 2

Electronic absorption spectrum of 3 in a DMF solution (10⁻³ M)

Fig. 3

ESR spectrum of 3

Fig. 4

ESR spectrum of 9

Fig. 5

Cyclic voltammograms of 1 (left), 2 (right)

Fig. 6

Biological screening of the ligand and its complexes against Gram-positive bacteria, Gram-negative bacteria, and fungi