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Synthesis and biological activity of previtamin D3 analogues with A-ring modifications

Authors :
Sánchez-Abella, Laura
Fernández, Susana
Verstuyf, Annemieke
Verlinden, Lieve
Gotor, Vicente
Ferrero, Miguel
Source :
Bioorganic & Medicinal Chemistry. Dec2008, Vol. 16 Issue 24, p10244-10250. 7p.
Publication Year :
2008

Abstract

Abstract: Synthesis of two novel 6-s-cis analogues of 1α,25-dihydroxyvitamin D3 are described using shikimic acid and its 4-epi isomer as versatile chiral starting materials. These derivatives contain a 2β-(3′-hydroxypropoxy) moiety or a 2β,3β-epoxy group into 1α,25-(OH)2-19-nor-pre-D3. The synthesized analogues were found to be not suitable for binding to the vitamin D receptor and showed weak binding affinity toward the vitamin D-binding protein. The new derivatives failed to inhibit cell proliferation. [Copyright &y& Elsevier]

Details

Language :
English
ISSN :
09680896
Volume :
16
Issue :
24
Database :
Academic Search Index
Journal :
Bioorganic & Medicinal Chemistry
Publication Type :
Academic Journal
Accession number :
35502836
Full Text :
https://doi.org/10.1016/j.bmc.2008.10.053