Investigation of a novel Schiff base Catena-((μ₆-(E)-2-((4-methoxy-2-oxidobenzylidene)ammonio)ethane-1-sulfonato potassium as a potential antibacterial agent

Context: Schiff bases, which have intriguing properties in many areas, have been studied extensively in recent years due to their structural properties and biological activities. In this research, a novel water-soluble Schiff base complex, Catena-((μ₆-(E)-2-((4-methoxy-2-oxidobenzylidene) ammonio) ethane-1-sulfonato potassium, C₁₀H₁₄KNO₆S (CMOAESP), was synthesized by a one-step condensation reaction of 2-hydroxy-4-methoxy benzaldehyde and taurine with the yield of 65%, 0.333 g. Spectral analysis of water-soluble crude product showed equilibria keto-enol tautomerism, by a resulting Zwitterionic form of the structure. The ADMET prediction showed that the CMOAESP obeys Lipinski's rule and was in bioavability range. The molecular docking results showed an inhibition ability for 1JIJ and MBT1 proteins which play an important role in antibacterial studies. The experimental end theoretical calculations were in a good agreement that CMOASP has inhibition efficiency against Escherichia coli and has inhibition at high concentrations against Staphylococcaceae aureus.

Methods: The WinGX software system SHELXS direct technique was used to solve the structure, and SHELXL full-matrix least-squares approach on F² was used to refine the results. The Gaussian 09W program was used to carry out the DFT calculations. The gap values for CMOAESP were calculated by using the B3LYP/6- 311 + + G(d,p) method in order to predict its reactivities and behaviors in the gas phase. The frontier orbitals, LUMO and HOMO together with some global parameters as electronegativity (μ), chemical potential (χ), hardness (η), electrophilicity index (ω), and softness (S) values were predicted from DFT calculations.