Bromodimethylsulfonium bromide: A novel reagent for the one pot synthesis of potent Nα-ureido peptides and study of molecular docking and antibacterial activities

Abstract

Abstract. N a -protected ureidopeptides were e ciently synthesized using bromodimethylsulfonium bromide mediated Curtius rearrangement through the in-situ generation of carboxylated sulfonium intermediate. Conversion of carboxylic acids to ureidopeptides in good yield was achieved in one pot under mild reaction conditions through a simple workup. To check the binding modes and binding a nity of urea functional group with target protein, the synthesized compounds were subjected to docking studies. Docking scores con rmed that the Boc-Leu-[NHCONH]-Ala-OMe and Leu-[NHCONH]-Ala-OMe molecules had the lowest energy and good agreement with the results of antibacterial studies against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeroginosa in comparison with streptomycin sulphate as a standard. The synthesized compounds were well characterized by IR, 1 H NMR, 13 C NMR, and mass spectral studies.