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Design, synthesis, activity evaluation and QSAR studies of novel antimalarial 1,2,3-triazolo-β-lactam derivatives

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Abstract

This paper describes the synthesis of some new β-lactam derivatives containing the 1,2,3-triazole moiety. All the compounds were evaluated for their in vitro antimicrobial and antimalarial activities. Moderate to excellent antimalarial activities were encountered. The results showed that compounds 5a, 5c, 5f, 5i exhibited the most potent antimalarial activity with IC50 values of 0.85, < 0.97, < 0.97, 1.81 µM against chloroquine-resistant P. falciparum K1 strain. A QSAR study highlights the structure–activity relationships that correlate the observed antimalarial activities with changes in the compounds’ structural features.

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Acknowledgements

The authors would like to thank the Shiraz University Research Council for financial support (Grant No. 96-GR-SC-23).

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Authors and Affiliations

  1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71946-84795, Iran

    Aliasghar Jarrahpour, Malihe Aye & Javad Ameri Rad

  2. Research Center for Health Sciences, Institute of Health, Department of Occupational Health Engineering, School of Health, Shiraz University of Medical Sciences, Shiraz, Iran

    Saeed Yousefinejad

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

    Véronique Sinou & Christine Latour

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

    Jean Michel Brunel

  5. Center for Molecular Diversity in Drug Design, Discovery, and Delivery, Department of Chemistry, University of South Florida, CHE 207, 4202 East Fowler Avenue, Tampa, FL, 33620, USA

    Edward Turos

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  1. Aliasghar Jarrahpour
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Correspondence to Aliasghar Jarrahpour.

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Jarrahpour, A., Aye, M., Rad, J.A. et al. Design, synthesis, activity evaluation and QSAR studies of novel antimalarial 1,2,3-triazolo-β-lactam derivatives. J IRAN CHEM SOC 15, 1311–1326 (2018). https://doi.org/10.1007/s13738-018-1330-2

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  • DOI: https://doi.org/10.1007/s13738-018-1330-2

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