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Synthesis and evaluation of biological activities of tripodal imines and β-lactams attached to the 1,3,5-triazine nucleus

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Abstract

A novel collection of tripodal β-lactam derivatives with 1,3,5-triazine as the central core is presented for the first time. The diastereoselective synthesis of tris-β-lactams was achieved via a [2 + 2] cycloaddition reaction between s-triazine-based tris-imines and activated aryloxyacetic acid derivatives. All the s-triazine hybrids were identified by FT-IR, 1H NMR, 13C NMR spectroscopies and elemental analysis, and found to have all-cis relative stereochemistry of the three β-lactams rings. The intermediate imines displayed moderate in vitro inhibitory activity against MCF-7 and HeLa cancer cell lines. The tris-β-lactams were tested against four kinds of bacteria including Gram-negative bacteria, E. coli and P. aeruginosa, a Gram-positive S. aureus and one capsulated Gram-negative K. pneumonia by the Kirby–Bauer disc diffusion method. Two compounds have shown moderate antibacterial activity against S. aureus, but not against the other bacteria, or fungal isolates C. albicans and A. fumigatus. The tris-β-lactams displayed good inhibitory behavior against the K562 human leukemia cell line, and antioxidant properties as radical scavengers.

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Acknowledgements

The authors would like to thank the Shiraz University Research Council for financial support (Grant No. 97-GR-SC-23).

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Authors and Affiliations

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

    Mohammad Bashiri & Aliasghar Jarrahpour

  2. Diagnostic Laboratory Science and Technology Research Center, School of Paramedical Science, Shiraz University of Medical Sciences, 71348-14336, Shiraz, Iran

    Banafsheh Rastegari

  3. Central Research Laboratory, Shiraz University of Medical Sciences, 71348-14336, Shiraz, Iran

    Aida Iraji

  4. Department of Medical Biotechnology, School of Advanced Medical Sciences and Technologies, Shiraz University of Medical Sciences, 71348-14336, Shiraz, Iran

    Cambyz Irajie

  5. Autoimmune Diseases Research Center, Shiraz University of Medical Sciences, 71348-14336, Shiraz, Iran

    Zahra Amirghofran

  6. Department of Immunology, Shiraz University of Medical Sciences, 71348-14336, Shiraz, Iran

    Zahra Amirghofran & Saeed Malek-Hosseini

  7. Shiraz HIV/AIDS Research, Center, Institute of Health, Shiraz University of Medical Sciences, 71348-14336, Shiraz, Iran

    Mohammad Motamedifar

  8. Department of Bacteriology and Virology, School of Medicine, Shiraz University of Medical Sciences, 71348-14336, Shiraz, Iran

    Mohammad Motamedifar & Mahtab Haddadi

  9. Department of Medical Mycology and Parasitology, School of Medicine, Shiraz University of Medical Sciences, 71348-14336, Shiraz, Iran

    Kamiar Zomorodian & Zahra Zareshahrabadi

  10. Department of Chemistry, Center for Molecular Diversity in Drug Design, Discovery, and Delivery, University of South Florida, 4202 E. Fowler Avenue, CHE 205, Tampa, FL, 33620, USA

    Edward Turos

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  1. Mohammad Bashiri
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  2. Aliasghar Jarrahpour
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Correspondence to Aliasghar Jarrahpour.

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Bashiri, M., Jarrahpour, A., Rastegari, B. et al. Synthesis and evaluation of biological activities of tripodal imines and β-lactams attached to the 1,3,5-triazine nucleus. Monatsh Chem 151, 821–835 (2020). https://doi.org/10.1007/s00706-020-02592-8

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  • DOI: https://doi.org/10.1007/s00706-020-02592-8

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