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

Research output: Contribution to journalArticle

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 1H and 13C spectra are reported herein. Finally, the effects of the synthesized amphiphilic steroid derivatives on the proliferation of cancer cells are reported and discussed.

Original languageEnglish
Pages (from-to)110-117
Number of pages8
JournalSteroids
Volume77
Issue number1-2
DOIs
Publication statusPublished - Jan 2012

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

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