A family of substituted hydrazonoisoxazolones with potential biological properties

Carlos Bustos, Elies Molins, Juan Guillermo Cárcamo, Marcelo N. Aguilar, Christian Sánchez, Ignacio Moreno-Villoslada, Hiroyuki Nishide, Ximena Zarate, Eduardo Schott

    Research output: Contribution to journalArticle

    3 Citations (Scopus)

    Abstract

    The synthesis, characterization and biological study of a new 3,4,5-trisubstituted isoxazolones have been reported, whereby a series of (Z)-3-methyl-4-(2-(R-phenyl)hydrazinylidene)isoxazol-5(4H)-ones were prepared by the reaction of a β-diketohydrazone with hydroxylammonium chloride. All the products were characterized using EA, UV-Vis, FT-IR, 1H-NMR, 13C-NMR spectroscopy and HMBC. The crystalline and molecular structures of three compounds were solved by X-ray diffraction methods. Density functional theory (DFT) and time-dependent DFT (TDDFT) calculations were performed to obtain a better explanation of the observed experimental behaviour of these newly synthetized compounds. Furthermore, the reports of cytotoxicity and an antiproliferative effect in human promyelocytic leukaemia cells, HL-60, was tested by the MTT reduction method, showing that most of the newly synthetized compounds had important antineoplastic activity. The most active isoxazolones were used in reverse transcription polymerase chain reaction (RT-PCR) experiments to determine the effect on the expression levels on mRNA encoding using the anti-apoptotic, Bcl 2, pro-apoptotic, Bax, and the proliferation inhibition, p21WAF-1, proteins. Therefore, it was possible to fully characterize the complete library of 15 isoxazolones and to show that most of them are antineoplastic trough an apoptotic pathway.

    Original languageEnglish
    Pages (from-to)2156-2167
    Number of pages12
    JournalNew Journal of Chemistry
    Volume40
    Issue number3
    DOIs
    Publication statusPublished - 2016

    Fingerprint

    Antineoplastic Agents
    Density functional theory
    Hydroxylamine
    Polymerase chain reaction
    Transcription
    Cytotoxicity
    Molecular structure
    Nuclear magnetic resonance spectroscopy
    Nuclear magnetic resonance
    Crystalline materials
    Proteins
    X ray diffraction
    Messenger RNA
    Experiments
    azastene

    ASJC Scopus subject areas

    • Chemistry(all)
    • Catalysis
    • Materials Chemistry

    Cite this

    Bustos, C., Molins, E., Cárcamo, J. G., Aguilar, M. N., Sánchez, C., Moreno-Villoslada, I., ... Schott, E. (2016). A family of substituted hydrazonoisoxazolones with potential biological properties. New Journal of Chemistry, 40(3), 2156-2167. https://doi.org/10.1039/c5nj02604k

    A family of substituted hydrazonoisoxazolones with potential biological properties. / Bustos, Carlos; Molins, Elies; Cárcamo, Juan Guillermo; Aguilar, Marcelo N.; Sánchez, Christian; Moreno-Villoslada, Ignacio; Nishide, Hiroyuki; Zarate, Ximena; Schott, Eduardo.

    In: New Journal of Chemistry, Vol. 40, No. 3, 2016, p. 2156-2167.

    Research output: Contribution to journalArticle

    Bustos, C, Molins, E, Cárcamo, JG, Aguilar, MN, Sánchez, C, Moreno-Villoslada, I, Nishide, H, Zarate, X & Schott, E 2016, 'A family of substituted hydrazonoisoxazolones with potential biological properties', New Journal of Chemistry, vol. 40, no. 3, pp. 2156-2167. https://doi.org/10.1039/c5nj02604k
    Bustos C, Molins E, Cárcamo JG, Aguilar MN, Sánchez C, Moreno-Villoslada I et al. A family of substituted hydrazonoisoxazolones with potential biological properties. New Journal of Chemistry. 2016;40(3):2156-2167. https://doi.org/10.1039/c5nj02604k
    Bustos, Carlos ; Molins, Elies ; Cárcamo, Juan Guillermo ; Aguilar, Marcelo N. ; Sánchez, Christian ; Moreno-Villoslada, Ignacio ; Nishide, Hiroyuki ; Zarate, Ximena ; Schott, Eduardo. / A family of substituted hydrazonoisoxazolones with potential biological properties. In: New Journal of Chemistry. 2016 ; Vol. 40, No. 3. pp. 2156-2167.
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