Synthesis, characterization, X-ray crystal structure, DFT calculation and antibacterial activities of new vanadium(IV, V) complexes containing chelidamic acid and novel thiourea derivatives

• Three new thiourea ligands and their oxido-vanadium(IV) complexes have synthesized.
• The complexation with vanadium leads to increment in the biological activity of thiourea ligands.
• The LUMO and HOMO energies have some relationship with antibacterial activities in these compounds.

Three new thiourea ligands derived from the condensation of aroyl- and aryl-isothiocyanate derivatives with 2,6-diaminopyridine, named 1,1′-(pyridine-2,6-diyl)bis(3-(benzoyl)thiourea) (L1), 1,1′-(pyridine-2,6-diyl)bis(3-(2-chlorobenzoyl)thiourea) (L2) and 1,1′-(pyridine-2,6-diyl)bis(3-(4-chlorophenyl)thiourea) (L3), their oxido-vanadium(IV) complexes, namely [VO(L1')(H2O)] (C1), [VO(L2')(H2O)] (C2) and [VO(L3')(H2O)] (C3), and also, dioxo-vanadium(V) complex containing 4-hydroxy-2,6-pyridine dicarboxylic acid (chelidamic acid, H2dipic-OH) and metformin (N,N-dimethylbiguanide, Met), named [H2Met][VO2(dipic-OH)]2·H2O (C4), were synthesized and characterized by elemental analysis, FTIR and 1H NMR and UV–visible spectroscopies. Proposed structures for free thiourea ligands and their vanadium complexes were corroborated by applying geometry optimization and conformational analysis. Solid state structure of complex [H2Met][VO2(dipic-OH)]2·H2O (triclinic, Pī) was fully determined by single crystal X-ray diffraction analysis. In this complex, metformin is double protonated and acted as counter ion. The antibacterial properties of these compounds were investigated in vitro against standard Gram-positive and Gram-negative bacterial strains. The experiments showed that vanadium(IV) complexes had the superior antibacterial activities than novel thiourea derivatives and vanadium(V) complex against all Gram-positive and Gram-negative bacterial strains.

Three new thiourea ligands, their oxo-vanadium(IV) complexes and oxo-vanadium(V) complex containing 4-hydroxy-2,6-pyridine dicarboxylic acid and metformin were synthesized. The antibacterial properties of all compounds were screened in vitro against standard bacterial strains.Figure optionsDownload as PowerPoint slide