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

A1 Originalartikel i en vetenskaplig tidskrift (referentgranskad)


Interna författare/redaktörer


Publikationens författare: Tiina Saloranta, István Zupkó, Jani Rahkila, Gyula Schneider, János Wölfling, Reko Leino
Förläggare: ELSEVIER SCIENCE INC
Publiceringsår: 2012
Tidskrift: Steroids
Tidskriftsakronym: STEROIDS
Volym: 77
Nummer: 1-2
Artikelns första sida, sidnummer: 110
Artikelns sista sida, sidnummer: 117
Antal sidor: 8
ISSN: 0039-128X


Abstrakt

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.


Nyckelord

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

Senast uppdaterad 2020-20-02 vid 05:36