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

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    8 Citations (Scopus)

    Abstract

    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.
    Original languageUndefined/Unknown
    Pages (from-to)110–117
    Number of pages8
    JournalSteroids
    Volume77
    Issue number1-2
    DOIs
    Publication statusPublished - 2012
    MoE publication typeA1 Journal article-refereed

    Keywords

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

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