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

Document Type: Article

Authors

1 Dept. of Chemistry, SIT, Affiliated to VTU, Tumakuru. Karntaka. India

2 Dept. of Chemistry, S.I.T., Tumakuru, Karnataka, INDIA

3 Dept. of Biotechnolgy, S.I.T., Tumakuru, Karnataka, INDIA

Abstract

Nα-protected ureidopeptides were synthesized efficiently 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 obtained in one-pot under mild reaction conditions, through a simple workup. To check the binding modes and binding affinity of urea functional group with target protein, the synthesized compounds were subjected to docking studies. Docking scores confirm that the molecules Boc-Leu-ψ[NHCONH]-Ala-OMe and Leu-ψ[NHCONH]-Ala-OMe have least energy and good agreement with the results of antibacterial studies against Escherichia coli, Staphylococcus aureus and Pseudomonas aeroginosa with respect to Streptomycin sulphate as a standard. The synthesized compounds were well characterized by IR, 1H NMR, 13C NMR and mass spectral studies.

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