Efficient synthesis of new azo-sulfonamide derivatives and investigation of their molecular docking and cytotoxicity results

Abstract

The present study focused on the synthesis, introduction and investigation of the biological effects of sulfonamide-derived products as new azo-sulfonamides (samples 1–6). In this transformation, the amine sulfonamide is first converted to the corresponding diazonium salt, which is then attacked by a nucleophilic carbon of the aromatic ring in the playing medium. All products were obtained with reasonable yields and high purity. The structure of synthesized derivatives was determined using various analytical tools including FT-IR, 1H NMR, 13C NMR and XRD spectroscopy, and the synthesized products were purified and identified. Biological properties of newly synthesized azo-compounds similar to SSZAD were also investigated. These compounds were tested in terms of biological effectiveness. The results of biochemical assays show that: the products have significant biological properties. MTT toxicity of compounds in breast cancer cells (MCF-7) for compounds 1–6 according to IC50 compare to Vinblastine is Vin > 5 > 4 > 6 > 2 > 3 > 1. The biochemical results obtained were analyzed by molecular docking interaction studies and showed strong hydrogen bonding with the target receptor. The docking calculation has been invoked to reveal the type of interactions that synthesized compounds can establish with the residues forming the active sites of the target proteins, 1FDW the three higher scores molecules appears to be (6 > 1 > 2), 3FC2 (the three highest binding affinities are in the order of 1 > 3 > 6), and 5GWK (three highest binding affinities are 1 > 3 > 6). The results indicate the effective interaction of all products with the targets. The molecular dynamics simulation has been invoked to study the presence of a stable system of the interacting protein–ligand.

Keywords

• Azo sulfonamide
• Antioxidant
• Cytotoxic
• Molecular docking
• MTT assay
• Molecular dynamic