Synthesis and Biological Activity of 22-Oxa CD-Ring Modified Analogues of 1α,25-Dihydroxyvitamin D3: cis-Perhydrindane CE-Ring Analogues
| Autor: | Roger Bouillon, Maurits Vandewalle, Dirk Van Haver, Pierre J. De Clercq, Wim Schepens, Annemieke Verstuyf |
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| Rok vydání: | 2004 |
| Předmět: |
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Molecular Calcitriol 1α 25 dihydroxyvitamin d3 Stereochemistry medicine.medical_treatment Clinical Biochemistry Molecular Conformation Pharmaceutical Science Breast Neoplasms Stereoisomerism Ring (chemistry) Biochemistry Chemical synthesis Calcitriol receptor Steroid Structure-Activity Relationship Cell Line Tumor Drug Discovery polycyclic compounds medicine Humans Structure–activity relationship Molecular Biology Chemistry Organic Chemistry Biological activity General Medicine Molecular Medicine Female Cell Division medicine.drug |
| Zdroj: | ChemInform. 35 |
| ISSN: | 1522-2667 0931-7597 |
| Popis: | The synthesis and biological activity of novel CD-ring modified analogues of 22-oxa-1α,25-dihydroxyvitamin D3, 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. |
| Databáze: | OpenAIRE |
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