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Synthesis, antibacterial activity, and CoMFA study of new 1,2,3-triazolyl 7-carboxamidodesacetoxy cephalosporanic acid derivatives

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Abstract

New derivatives of 1,2,3-triazolyl 7-carboxamidodesacetoxy cephalosporanic acid were synthesized using alkyne-azide 1,3-dipolar cycloaddition. The synthesized compounds were evaluated for their antibacterial activity against a collection of Gram-positive and Gram-negative bacteria and also in synergy with cefixime and cephalexin. Some compounds inhibited vancomycin-resistant strain of Enterococcus faecium (MIC = 8 µg/mL) and in the synergy experiments compounds 13a, 13f, and 13g decreased the level of MIC against an ESBL strain of Klebsiella pneumonia. A comparative molecular field analysis has been carried out, and the effect of substituents on the antibacterial activities of the synthesized compounds was explained.

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Acknowledgments

The authors wish to thanks the Iran’s National Elites Foundation (INEF) for partial financial support. The cooperation of Division of Pharmaceutical Biology, University of Basel, Switzerland, for running the HRMS spectra is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, 1983963113, Tehran, Iran

    Maryam Mohebbi, Peyman Salehi & Morteza Bararjanian

  2. Department of Biology, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, 1983963113, Tehran, Iran

    Atousa Aliahmadi

  3. Department of Chemistry, Faculty of Sciences, K. N. Toosi University of Technology, 1983963113, Tehran, Iran

    Reihaneh Safavi-Sohi & Jahan B. Ghasemi

Authors
  1. Maryam Mohebbi
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  2. Peyman Salehi
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  3. Morteza Bararjanian
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  4. Atousa Aliahmadi
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  5. Reihaneh Safavi-Sohi
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  6. Jahan B. Ghasemi
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Correspondence to Peyman Salehi.

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Mohebbi, M., Salehi, P., Bararjanian, M. et al. Synthesis, antibacterial activity, and CoMFA study of new 1,2,3-triazolyl 7-carboxamidodesacetoxy cephalosporanic acid derivatives. Med Chem Res 23, 4531–4541 (2014). https://doi.org/10.1007/s00044-014-1014-0

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  • DOI: https://doi.org/10.1007/s00044-014-1014-0

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