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Synthesis and biological evaluation of some new β-lactam-triazole hybrids

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Abstract

A series of novel β-lactams was synthesized from different imines and a special ketene derived from N-endo-5-norbornene-2,3-dicarboxyloylglycine 1 via the [2 + 2] ketene imine cycloaddition. Then, β-lactams 3a–h were treated with 1-azido-4-nitrobenzene 4 to afford β-lactam-triazole hybrids 5a–h. Of the twenty-three β-lactams tested against chloroquine-resistant P. falciparum K14 strain, 3a and 3d showed IC50 < 20 µM, while 3j, 3m, 5a–5f exhibited IC50 < 50. These newly synthesized β-lactams were also tested against S. aureus, E. coli, P. aeruginosa, C. albicans and C. glabrata and showed no activity below 125 µg/mL.

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Acknowledgments

Funding for this research was generously provided by the Shiraz University Research Council (Grant No. 93-GR-SC-23).

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Authors and Affiliations

  1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran

    Aliasghar Jarrahpour & Pouria Shirvani

  2. UMR-MD3 Relation hôte-parasites, Physiopathologie & Pharmacologie, Faculté de pharmacie, Aix-Marseille Université, Bd Jean Moulin, 13385, Marseille, France

    Véronique Sinou & Christine Latour

  3. Centre de Recherche en Cancérologie de Marseille (CRCM), CNRS, UMR7258, Institut PaoliCalmettes, Inserm, U1068, Faculté de Pharmacie, Aix-Marseille Université, UM 105, 27 Bd Jean Moulin, 13385, Marseille Cedex 05, France

    Jean M. Brunel

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  1. Aliasghar Jarrahpour
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  3. Véronique Sinou
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Correspondence to Aliasghar Jarrahpour.

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Jarrahpour, A., Shirvani, P., Sinou, V. et al. Synthesis and biological evaluation of some new β-lactam-triazole hybrids. Med Chem Res 25, 149–162 (2016). https://doi.org/10.1007/s00044-015-1474-x

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  • DOI: https://doi.org/10.1007/s00044-015-1474-x

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