Advanced search

Development of Analogues of 1 alpha,25-Dihydroxyvitamin D-3 with Biased Side-Chain Orientation: C20 Methylated Des-C,D-homo Analogues

(2009) EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 11(Sp. Iss. SI). p.1720-1737
Author
Organization
Abstract
The discovery that 1 alpha,25-dihydroxyvitamin D-3 is effective in the inhibition of cellular proliferation and in the induction of cellular differentiation has led to a search for analogues in which these activities and the classical calcemic activity of the hormone are dissociated. In this context, the synthesis and biological evaluation are reported for six CD-ring modified structural analogues that were conceived so as to enforce a particular orientation of the 25-hydroxylated side chain. The analogues are characterized by the absence of the C-ring and the presence of an unnatural six-membered D-ring. The biased side-chain orientations are realized through the stereocontrolled incorporation of methyl substituents at positions C13/C20 and C16/C20. Comparison of the results of the biological evaluation and conformational analysis of the side chain confirms the existence of a relationship between inhibition of MCF-7 breast cancer cell proliferation and side chain geometry. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Keywords
Vitamins, Conformation analysis, Structure-activity relationships, Calcitriol

Citation

Please use this url to cite or link to this publication:

Chicago
Vrielynck, Freek, Dirk Van Haver, Maurits Vandewalle, Lieve Verlinden, Annemieke Verstuyf, Roger Bouillon, Gianluca Croce, and Pierre De Clercq. 2009. “Development of Analogues of 1 alpha,25-Dihydroxyvitamin D-3 with Biased Side-Chain Orientation: C20 Methylated Des-C,D-homo Analogues.” Ed. Haymo Ross. European Journal of Organic Chemistry 11 (Sp. Iss. SI): 1720–1737.
APA
Vrielynck, F., Van Haver, D., Vandewalle, M., Verlinden, L., Verstuyf, A., Bouillon, R., Croce, G., et al. (2009). Development of Analogues of 1 alpha,25-Dihydroxyvitamin D-3 with Biased Side-Chain Orientation: C20 Methylated Des-C,D-homo Analogues. (H. Ross, Ed.)EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 11(Sp. Iss. SI), 1720–1737.
Vancouver
1.
Vrielynck F, Van Haver D, Vandewalle M, Verlinden L, Verstuyf A, Bouillon R, et al. Development of Analogues of 1 alpha,25-Dihydroxyvitamin D-3 with Biased Side-Chain Orientation: C20 Methylated Des-C,D-homo Analogues. Ross H, editor. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. Wiley-VCH; 2009;11(Sp. Iss. SI):1720–37.
MLA
Vrielynck, Freek et al. “Development of Analogues of 1 alpha,25-Dihydroxyvitamin D-3 with Biased Side-Chain Orientation: C20 Methylated Des-C,D-homo Analogues.” Ed. Haymo Ross. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 11.Sp. Iss. SI (2009): 1720–1737. Print.
@article{667759,
  abstract     = {The discovery that 1 alpha,25-dihydroxyvitamin D-3 is effective in the inhibition of cellular proliferation and in the induction of cellular differentiation has led to a search for analogues in which these activities and the classical calcemic activity of the hormone are dissociated. In this context, the synthesis and biological evaluation are reported for six CD-ring modified structural analogues that were conceived so as to enforce a particular orientation of the 25-hydroxylated side chain. The analogues are characterized by the absence of the C-ring and the presence of an unnatural six-membered D-ring. The biased side-chain orientations are realized through the stereocontrolled incorporation of methyl substituents at positions C13/C20 and C16/C20. Comparison of the results of the biological evaluation and conformational analysis of the side chain confirms the existence of a relationship between inhibition of MCF-7 breast cancer cell proliferation and side chain geometry. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)},
  author       = {Vrielynck, Freek and Van Haver, Dirk and Vandewalle, Maurits and Verlinden, Lieve and Verstuyf, Annemieke and Bouillon, Roger and Croce, Gianluca and De Clercq, Pierre},
  editor       = {Ross, Haymo},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {Vitamins,Conformation analysis,Structure-activity relationships,Calcitriol},
  language     = {eng},
  number       = {Sp. Iss. SI},
  pages        = {1720--1737},
  publisher    = {Wiley-VCH},
  title        = {Development of Analogues of 1 alpha,25-Dihydroxyvitamin D-3 with Biased Side-Chain Orientation: C20 Methylated Des-C,D-homo Analogues},
  url          = {http://dx.doi.org/10.1002/ejoc.200801183},
  volume       = {11},
  year         = {2009},
}

Altmetric
View in Altmetric
Web of Science
Times cited: