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A-Ring-Modified 2-Hydroxyethylidene Previtamin D3 Analogues: Synthesis and Biological Evaluation

Author:
Hernández Martín, AlbaUniovi authority; Fernández González, SusanaUniovi authority; Verstuyf, Annemieke; Verlinden, Lieve; Ferrero Fuertes, MiguelUniovi authority
Subject:

Previtamin D analogues

A-ring modified

Biological assays

Publication date:
2017
Editorial:

Wiley

Publisher version:
http://dx.doi.org/10.1002/ejoc.201601263
Citación:
European Journal of Organic Chemistry, 3, p. 504-513 (2017); doi:10.1002/ejoc.201601263
Descripción física:
p. 504-513
Abstract:

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.

URI:
http://hdl.handle.net/10651/40136
ISSN:
1434-193X; 1099-0690
DOI:
10.1002/ejoc.201601263
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.

Id. Proyecto:

MICINN/CTQ2011-24237

MICINN/CTQ2014-55015-P

Principado de Asturias/FC-15-GRUPIN14-002

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