Synthesis and biological activity of 22-oxa CD-ring modified analogues of 1alpha,25-dihydroxyvitamin D3: cis-perhydrindane CE-ring analogues

The synthesis and biological activity of novel CD-ring modified analogues of 22-oxa-1alpha,25-dihydroxyvitamin D(3), lacking the D-ring and featuring a connection between C-12 and C-21 (cis-perhydrindane CE-ring analogues), is described. The synthesis of the CE-ring system follows Meyers' metho...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2004-08, Vol.14 (15), p.3885-3888
Main Authors: Demin, Samuël, Van Haver, Dirk, Vandewalle, Maurits, De Clercq, Pierre J, Bouillon, Roger, Verstuyf, Annemieke
Format: Article
Language:English
Subjects:
Breast Neoplasms
Calcitriol - analogs & derivatives
Calcitriol - chemical synthesis
Calcitriol - chemistry
Calcitriol - pharmacology
Cell Division - drug effects
Cell Line, Tumor
Female
Humans
Models, Molecular
Molecular Conformation
Stereoisomerism
Structure-Activity Relationship
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Summary:The synthesis and biological activity of novel CD-ring modified analogues of 22-oxa-1alpha,25-dihydroxyvitamin D(3), lacking the D-ring and featuring a connection between C-12 and C-21 (cis-perhydrindane CE-ring analogues), is described. The synthesis of the CE-ring system follows Meyers' methodology for the preparation of enantiomerically pure hydrinden-2-ones. The analogues show a complete lack of binding affinity for the vitamin D receptor (pig nVDR) and of antiproliferative activity (MCF-7 cells), as compared to calcitriol.
ISSN:0960-894X