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

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.