A-Ring-Modified 2-Hydroxyethylidene Previtamin D3 Analogues: Synthesis and Biological Evaluation
Autor(es) y otros:
Palabra(s) clave:
Previtamin D analogues
A-ring modified
Biological assays
Fecha de publicación:
Editorial:
Wiley
Versión del editor:
Citación:
Descripción física:
Resumen:
To investigate the biological profile of the previtamin form of vitamin D, we have synthesized new analogues of 19-nor-1α,25-dihydroxyprevitamin D3 bearing a 2-hydroxyethylidene moiety at the A-ring. The target compounds were prepared by convergent synthesis employing the 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 starting material for the synthesis of the A-ring precursors. The binding affinity to Vitamin D Receptor (VDR) and Vitamin D Binding Protein (DBP), and MCF-7 cell antiproliferative activity have been evaluated.
To investigate the biological profile of the previtamin form of vitamin D, we have synthesized new analogues of 19-nor-1α,25-dihydroxyprevitamin D3 bearing a 2-hydroxyethylidene moiety at the A-ring. The target compounds were prepared by convergent synthesis employing the 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 starting material for the synthesis of the A-ring precursors. The binding affinity to Vitamin D Receptor (VDR) and Vitamin D Binding Protein (DBP), and MCF-7 cell antiproliferative activity have been evaluated.
Patrocinado por:
Financial support by the Spanish Ministerio de Ciencia e Innovación (MICINN) (Projects CTQ2011-24237 and CTQ2014-55015-P) and Principado de Asturias (Project FC-15-GRUPIN14-002) are gratefully acknowledged. A. H.-M. thanks the Spanish Ministerio de Educación for a pre-doctoral FPU fellowship.
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