Synthesis of new simplified hemiasterlin derivatives with α,β-unsaturated carbonyl moiety

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Abstract

In this Letter, we report a convenient and efficient method for the synthesis of new simplified derivatives of hemiasterlin in which the α,α-dimethylbenzylic moiety A is replaced by α,β-unsaturated aryl groups as Michael acceptor. Most of these derivatives have a strong cytotoxic activity on three human tumor cell lines (KB, Hep-G2 and MCF7). Analogs 17b and 17f showed a high cytotoxicity against KB and Hep-G2 cancer cell lines comparable to paclitaxel and ellipticine.

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Acknowledgment

This work was financially supported in part by scientific research and technological development project (code: ĐT.NCCB-ĐHUD.2011-G/07).

References and notes (12)

  • R. Talpir et al.

    Tetrahedron Lett.

    (1994)
  • W.R. Gamble et al.

    Bioorg. Med. Chem.

    (1999)
  • J.E. Coleman et al.

    Tetrahedron

    (1995)
  • Y. Yamazaki et al.

    J. Med. Chem.

    (2012)
  • R.M. Herbst et al.

    Org. Synth.

    (1939)
    C. Thomas et al.

    Tetrahedron Lett.

    (2010)
    M.A. Mesaik et al.

    Bioorg. Med. Chem.

    (2004)
    T.V. RajanBabu et al.

    J. Org. Chem.

    (1997)
    M. Cutolo et al.

    Tetrahedron Lett.

    (1983)
    (f)Baell, J. B.; Garrett, T. P. J.; Hogarth, P. M.; Mattews, B. R.; McCarthy, T. D.; Pietersz, G. A....S.D. Sawant et al.

    J. Appl. Chem.

    (2013)
    M. Blanco-Lomas et al.

    Eur. J. Org. Chem.

    (2013)
    I. Funes-Ardoiz et al.

    Tetrahedron

    (2013)
  • J.A. Murphy et al.

    Org. Lett.

    (2005)
There are more references available in the full text version of this article.

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