Synthesis of Schiff base (E)-4-((2-hydroxy-3,5-diiodobenzylidene)amino)-N-thiazole-2-yl)benzenesulfonamide with antimicrobial potential, structural features, experimental biological screening and quantum mechanical studies

Abstract

We report the synthesis and characterisation of the Schiff base (E)-4-((2-hydroxy-3,5-diiodobenzylidene)amino)-N-thiazole-2-yl) benzene sulfonamide (DITH) prepared the by condensation of 3,5-diiodosalicylaldehyde and sulfathiazole. The synthesised compound was characterised with spectral techniques like FTIR, 1HNMR and UV-Visible spectroscopy. The molecule was optimised using computational methods employing DFT/B3LYP/cc-pVDZ/Lanldz(I) basis sets followed by the simulation of the vibrational spectra, scaled and compared with experimental spectra for vibrational assignment and potential energy distribution. The 1HNMR calculated from the standard GIAO method with DMSO as a solvent was also compared with experimental spectra. The UV-Vis spectrum calculated using TD-DFT/CAM-B3LYP/cc-pVDZ/Lanl2dz(I). Wave function based properties like localised orbital locator, electron localisation function and non-covalent interactions has been studied extensively. The compound DITH's pharmacodynamic indicated that the compound has excellent drug-likeness properties. Prediction of the activity and structure spectra (PASS) studies predicted that it has anti-infective properties, confirmed by a docking score of -7.1 and -7.2 kcal/mol for antibacterial and antifungal properties. Experimental studies show that the newly synthesised Schiff base shows significant inhibition of bacteria and fungi growth compared to standard drugs.