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

Demin, S.ël.; Van Haver, D.; Vandewalle, M.; De Clercq, P.J.; Bouillon, R.; Verstuyf, A.

Bioorganic and Medicinal Chemistry Letters 14(15): 3885-3888


ISSN/ISBN: 0960-894X
PMID: 15225690
DOI: 10.1016/j.bmcl.2004.05.067
Accession: 012609984

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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.