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Synthesis and antibacterial activity of new chiral N-sulfamoyloxazolidin-2-ones

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Abstract

A new series of N, \(N^{\prime }\)-bis-oxazolidinones-sulfone and 5-chloromethylsulfamoyl-oxazolidin-2-ones have been synthesized in three steps (carbamoylation, sulfamoylation and cyclization) starting from 1,3-dichloroporopan-2-ol, chlorosulfonyl isocyanate and primary or secondary amines. Synthesis has been carried out following simple methodology in excellent isolated yields. The structure and purity of the original compounds were confirmed by IR, NMR, and MS. The compounds were evaluated for their in vitro antibacterial activity against some Gram-positive bacteria; Staphylococcus aureus and Gram-negative bacteria; Escherichia Coli, Klebsiella pneumonieae, Acinetobacter, Pseudomonas aeruginosa, Enterococcus, Salmonella sp. The compounds showed moderate to good antibacterial activity.

We have developed the synthesis of news series of 5-chloromethylsulfamoyl-oxazolidinone and N,N'-bis-oxazolidinones-sulfone in three steps, starting from 1,3-dichloroporopan-2-ol, and chlorosulfonyl isocyanate. The structure of all compounds was confirmed by usual spectroscopic methods. The in vitro antibacterial activity of these compounds was evaluated.

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Acknowledgments

This work was generously supported by the Direction Générale de la Recherche Scientifique et du Développement Technologique, DGRS-DT, Algerian Ministry of Scientific Research (FNR 2000).

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Authors and Affiliations

  1. Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar, Annaba University, Box 12, 23000, Annaba, Algeria

    FOUZIA BOUCHAREB, MALIKA BERREDJEM, ABDESLEM BOUZINA, BILLEL BELHANI & NOUR-EDDINE AOUF

  2. Laboratory of virology-bacteriology, University Hospital Center Touhami Benflis, Batna, 05000, Algeria

    SAMIRA AIT KAKI & AMEL BOUARICHA

Authors
  1. FOUZIA BOUCHAREB
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  2. MALIKA BERREDJEM
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  3. SAMIRA AIT KAKI
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  4. AMEL BOUARICHA
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  5. ABDESLEM BOUZINA
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  6. BILLEL BELHANI
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  7. NOUR-EDDINE AOUF
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Corresponding author

Correspondence to MALIKA BERREDJEM.

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Supplementary Information

All additional information pertaining to characterization of the N-sulfamoyloxazolidin-2-ones using ESI-MS technique (figures S14, S15), 1H NMR spectrum (figures S8, S10, S12, S13), 13C NMR spectrum (figures S9, S11), are given in the supporting information which available at www.ias.ac.in/chemsci.

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BOUCHAREB, F., BERREDJEM, M., KAKI, S.A. et al. Synthesis and antibacterial activity of new chiral N-sulfamoyloxazolidin-2-ones. J Chem Sci 128, 85–91 (2016). https://doi.org/10.1007/s12039-015-1004-x

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  • DOI: https://doi.org/10.1007/s12039-015-1004-x

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