4-Bromobenzene Sulfonate Derivatives: Synthesis, Characterization, DFT and Molecular Docking Study

Area of Science:

• Computational Chemistry
• Molecular Modeling
• Medicinal Chemistry

Background:

• 4-bromobenzenesulfonate derivatives are of interest for their potential biological activities.
• Understanding molecular structure and electronic properties is crucial for drug discovery.

Purpose of the Study:

• To synthesize and characterize novel 4-bromobenzenesulfonate derivatives (I and II).
• To investigate the electronic, structural, and NLO properties using DFT.
• To evaluate the therapeutic potential of these compounds against specific receptor proteins.

Main Methods:

• Synthesis and characterization using FTIR and NMR spectroscopy.
• Density Functional Theory (DFT) calculations including B3LYP/6-311++G(d,p) level.
• Natural Bond Orbital (NBO) analysis for stability and charge delocalization.
• Molecular docking simulations against EGFR, VEGFR1, acetylcholinesterase, and Leishmania infantum trypanothione reductase.

Main Results:

• Experimental and computational vibrational frequencies showed good agreement.
• Optimized molecular structures, UV-Vis, and NLO properties were determined.
• NBO analysis confirmed molecular stability via hyperconjugation and charge delocalization.
• HOMO-LUMO analysis indicated intramolecular charge transfer.
• Molecular docking revealed significant binding energies and inhibition constants for compounds I and II against the tested receptors.

Conclusions:

• The synthesized 4-bromobenzenesulfonate derivatives possess favorable electronic and structural properties.
• Computational methods accurately predicted experimental vibrational frequencies.
• The compounds exhibit therapeutic potential, warranting further investigation for drug development against cancer and parasitic infections.