Increasing the amphiphilicity of an estradiol based steroid structure by Barbier-allylation - ring-closing metathesis - dihydroxylation sequence

Tiina Saloranta, István Zupkó, Jani Rahkila, Gyula Schneider, János Wölfling, Reko Leino

    Forskningsoutput: TidskriftsbidragArtikelVetenskapligPeer review

    8 Citeringar (Scopus)

    Sammanfattning

    Polyhydroxylated steroids, such as brassinosteroids, phytoecdysteroids and steroid saponins, are structurally attractive compounds possessing a number of interesting biological properties. Accordingly, development of synthetic procedures to build steroid based structures mimicking the naturally occurring hydrophilic steroids is of topical interest. In the present work, a D-secoestrone derivative was modified further by Barbier-allylation - ring-closing metathesis - dihydroxylation sequence with the aim to prepare steroid based structures with limited hydrophilicity. A straightforward synthesis route was developed with the isolated yield for each step ranging from good to excellent. All compounds prepared were fully characterized by NMR spectroscopic techniques and completely assigned H-1 and C-13 spectra are reported herein. Finally, the effects of the synthesized amphiphilic steroid derivatives on the proliferation of cancer cells are reported and discussed. (C) 2011 Elsevier Inc. All rights reserved.
    OriginalspråkOdefinierat/okänt
    Sidor (från-till)110–117
    Antal sidor8
    TidskriftSteroids
    Volym77
    Utgåva1-2
    DOI
    StatusPublicerad - 2012
    MoE-publikationstypA1 Tidskriftsartikel-refererad

    Nyckelord

    • Amphiphilicity
    • Barbier-allylation
    • Dihydroxylation
    • Estradiol
    • Ring-closing metathesis

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