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Synthesis of 2-ethyl-19-nor analogs of 1α,25-dihydroxyvitamin D₃

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Abstract
The synthesis of two new A-ring precursors, useful for the convergent assembly of 2α-ethyl and 2β-ethyl derivatives of 19-nor-1α,25-dihydroxyvitamin D3, is described. These building blocks were prepared in 14 steps from quinic acid, which led to a new and practical synthesis of 2α-ethyl-14-epi-19-nor-20-epi-23-yne-1,25(OH)2D3, an analog that shows a remarkably low calcemic effect in mice, while retaining the ability to promote cell differentiation and to inhibit cell proliferation in a number of human cancer cell lines.
Keywords
Medicinal chemistry, Drug discovery, Stereocontrolled synthesis, Chiral pool, Vitamins, VITAMIN-D, 1, 25-DIHYDROXYVITAMIN D-3, BIOLOGICAL-ACTIVITIES, CANCER CELLS, GROWTH, 2-METHYL, SYSTEM

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Chicago
Laplace, Duchan, Michel Van Overschelde, Pierre De Clercq, Annemieke Verstuyf, and Johan Winne. 2013. “Synthesis of 2-ethyl-19-nor Analogs of 1α,25-dihydroxyvitamin D₃.” European Journal of Organic Chemistry (4): 728–735.
APA
Laplace, D., Van Overschelde, M., De Clercq, P., Verstuyf, A., & Winne, J. (2013). Synthesis of 2-ethyl-19-nor analogs of 1α,25-dihydroxyvitamin D₃. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (4), 728–735.
Vancouver
1.
Laplace D, Van Overschelde M, De Clercq P, Verstuyf A, Winne J. Synthesis of 2-ethyl-19-nor analogs of 1α,25-dihydroxyvitamin D₃. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2013;(4):728–35.
MLA
Laplace, Duchan, Michel Van Overschelde, Pierre De Clercq, et al. “Synthesis of 2-ethyl-19-nor Analogs of 1α,25-dihydroxyvitamin D₃.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 4 (2013): 728–735. Print.
@article{3256661,
  abstract     = {The synthesis of two new A-ring precursors, useful for the convergent assembly of 2α-ethyl and 2β-ethyl derivatives of 19-nor-1α,25-dihydroxyvitamin D3, is described. These building blocks were prepared in 14 steps from quinic acid, which led to a new and practical synthesis of 2α-ethyl-14-epi-19-nor-20-epi-23-yne-1,25(OH)2D3, an analog that shows a remarkably low calcemic effect in mice, while retaining the ability to promote cell differentiation and to inhibit cell proliferation in a number of human cancer cell lines.},
  author       = {Laplace, Duchan and Van Overschelde, Michel and De Clercq, Pierre and Verstuyf, Annemieke and Winne, Johan},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {Medicinal chemistry,Drug discovery,Stereocontrolled synthesis,Chiral pool,Vitamins,VITAMIN-D,1,25-DIHYDROXYVITAMIN D-3,BIOLOGICAL-ACTIVITIES,CANCER CELLS,GROWTH,2-METHYL,SYSTEM},
  language     = {eng},
  number       = {4},
  pages        = {728--735},
  title        = {Synthesis of 2-ethyl-19-nor analogs of 1α,25-dihydroxyvitamin D₃},
  url          = {http://dx.doi.org/10.1002/ejoc.201201261},
  year         = {2013},
}

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