Synthesis, spectral analysis, antibacterial activity, quantum chemical studies and supporting molecular docking of Schiff base (E)-4-((4-bromobenzylidene) amino)benzenesulfonamide

A new Schiff base (E)-4-((4-bromobenzylidene) amino) benzenesulfonamide (M2) was synthesized by the reaction between 4-bromobenzaldehyde and sulfanilamide followed by characterization using IR, Raman, UV–Visible, 1HNMR, and 13CNMR spectral techniques. This was followed by electronic structure studie...

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Veröffentlicht in:Journal of the Indian Chemical Society 2022-05, Vol.99 (5), p.100405, Article 100405
Hauptverfasser: Muthukumar, R., Karnan, M., Elangovan, N., Karunanidhi, M., Thomas, Renjith
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Sprache:eng
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Zusammenfassung:A new Schiff base (E)-4-((4-bromobenzylidene) amino) benzenesulfonamide (M2) was synthesized by the reaction between 4-bromobenzaldehyde and sulfanilamide followed by characterization using IR, Raman, UV–Visible, 1HNMR, and 13CNMR spectral techniques. This was followed by electronic structure studies using DFT and TD-DFT. We simulated the IR spectrum using B3LYP/6-31+G(d,p) level of theory, followed by a comparison with experimental spectra and detailed potential energy distribution and vibrational assignment analysis. The comparison of experimental UV and simulated UV spectrum using TD-DFT B3LYP/6-31+G(d,p) in DMSO solvent atmosphere gave good agreement. As Schiff bases are biologically active, we checked for the potential activity of the synthesized compound with the help of ADMET prediction and found it to be active. Wavefunctions related properties like ELF, LOL, and ELF are also reported. Prediction of biological activity spectrum study indicated possible antibacterial activity against bacteria, which is supported by molecular docking against Staphylococcus aureus (3U2D) protein with a docking score of −7.1 kcal/mol. Experimental antibacterial study using the compound and standard drugs confirmed this prediction. [Display omitted] •Synthesis of Schiff's base from 4-bromobenzaldehydel and sulfanilamide.•Detailed structure, FTIR, FT-Raman, 1H NMR, 13C NMR characterization performed and vibrational frequency assignment and potential energy distribution reported.•The compound is a drug candidate and shows excellent docking against staphylococcus aureus (3U2D) protein.•Anti-bacterial study the compound highest activity compare to standard drug.•The LOL, ELF, ALIE and RDG also reported.
ISSN:0019-4522
DOI:10.1016/j.jics.2022.100405