Synthesis, molecular structure, spectroscopic properties and biological evaluation of 4-substituted-N-(1H-tetrazol-5-yl)benzenesulfonamides: Combined experimental, DFT and docking study

Publication date: Available online 20 May 2019Source: Journal of Molecular StructureAuthor(s): Tehmina Akram, Muhammad Athar Abbasi, Ayyaz Mahmood, Edna Barboza de Lima, Fouzia Perveen, Muhammad Ashraf, Irshad Ahmad, S. Goumri-SaidAbstractSynthesis, molecular, spectroscopic (1H NMR and FT–IR) properties, biological evaluation, electronic structure calculations and in silico molecular docking of two sulfonamide derivates, namely the 4-Bromo-N-(1H-tetrazol-5-yl)benzenesulfonamide (4) and 4-Nitro-N-(1H-tetrazol-5-yl)benzenesulfonamide (5) were reported. Density Functional Theory (DFT) calculations were performed using B3LYP/6-311++G(d,p) to further investigate the molecular, electronic structures and to assist the spectral assignments and provide the useful structural and spectroscopic information. A conformational analysis was completed to obtain stable structures. The simulated 1H NMR and FT–IR spectra were compared with those obtained experimentally and any observed discrepancies were discussed. The synthesized compounds were tested against one Gram-positive, Bacillus subtilis (+), and three Gram-negative, Salmonella typhi (–), Escherichia coli (–), Pseudomonas aeruginosa (–), bacteria. Results show that the compound 5 is highly active antibacterial agent. Carbonic Anhydrase Inhibition and cytotoxicity assay results refer the compounds to be a moderate inhibitor of Carbonic Anhydrase enzyme. The molecular docking results support the experimental observations. The bi...
Source: Journal of Molecular Structure - Category: Molecular Biology Source Type: research