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Synthesis and Antimicrobial Activity of Vanadium and Iron Complexes with trans 3,4-methylenedioxycinnamic Acid

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The trans-3,4-methylenedioxycinnamic acid is derived from cinnamic acid, a precursor of several phenylpropanoids, which is biologically active and commonly found in plants, mainly in the essential oils of cinnamon and coca leaves [1,2]. This acid and its derivatives have several biological activities [3], in particular trans-3,4-methylenedioxycinnamic acid exhibits antimicrobial activity [4,5]. It may also be used as a binder in various transition metal complexation reactions and employed in the synthesis of biologically active compounds. In this context, the objective of the work was directed to the synthesis and antimicrobial potential of hybrid compounds using as binder trans-3,4-methylenedioxycinnamic acid complexed with vanadium and iron. Acid, vanadyl sulfate and ferric chloride were purchased commercially. The acid/vanadium (A-V) and acid/iron (A-F) complexes were obtained from the reaction of the salts with the acid in basic ethanolic medium with stirring for 4h at 40°C. After treatment of the reaction mixtures, the complexes were obtained as greenish-colored solids with yields of 80% (A-V) and 75% (A-F). The chemical structures of the complexes were elucidated based on the interpretations of the data of their IR, and UV-Vis spectra. The antimicrobial potential of the complexes was evaluated by determining their Minimal Inhibitory Concentrations (MICs) for the bacteria Staphylococcus aureus, Escherichia coli and for the fungi Microsporum gypseum and Epidermophyton floccosum. The complex with the highest antimicrobial activity was A-F against S. aureus bacteria with MIC of 312.5 μg/mL and against Epidermophyton floccosum with MIC of 625 μg/mL. Two new complexes having as ligand a natural compound were synthesized and showed antimicrobial activity, and the complexes showed solubility in aqueous medium when compared to the free ligand, a relevant physical property for drug candidate compounds.