Details

Autor(en) / Beteiligte

• Hernández‐Martín, Alba
• Fernández, Susana
• Verstuyf, Annemieke
• Verlinden, Lieve
• Ferrero, Miguel

Titel

A‐Ring‐Modified 2‐Hydroxyethylidene Previtamin D 3 Analogues: Synthesis and Biological Evaluation

Ist Teil von

• European journal of organic chemistry, 2017-01, Vol.2017 (3), p.504-513

Erscheinungsjahr

2017

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• To investigate the biological profile of the previtamin form of vitamin D, we synthesized new analogues of 19‐ nor ‐1α,25‐dihydroxyprevitamin D 3 bearing a 2‐hydroxyethylidene moiety at the A‐ring. The target compounds were prepared by convergent synthesis using a Sonogashira coupling between an A‐ring enyne synthon and a CD‐ring/side‐chain vinyl triflate. We have demonstrated the versatility of shikimic acid as a starting material for the synthesis of the A‐ring precursors. The binding affinity to vitamin D receptor (VDR) and human vitamin D binding protein (hDBP), and the MCF‐7 cell antiproliferative activity were evaluated.