Total synthesis of 25-hydroxy-16,23E-diene vitamin D3 and 1 alpha,25-dihydroxy-16,23E-diene vitamin D3: separation of genomic and nongenomic vitamin D activities

Separation of genomic and nongenomic vitamin D activities was achieved by structural modification of 1,25-dihydroxy vitamin D3 by introduction of 16 and 23E double bonds. The modified compound 3, lacking a 1 alpha-hydroxy group, exhibits only nongenomic activity. Its 1 alpha-hydroxy relative 4 expre...

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Veröffentlicht in:	Bioorganic & medicinal chemistry 1998-11, Vol.6 (11), p.2051-2059
Hauptverfasser:	Kabat, M M, Burger, W, Guggino, S, Hennessy, B, Iacobelli, J A, Takeuchi, K, Uskoković, M R
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Calcifediol - pharmacology Calcitriol - pharmacology Calcium - metabolism Calcium Channels - drug effects Calcium Channels - physiology Cell Line Cell Membrane - drug effects Cell Membrane - physiology Cells, Cultured Cholecalciferol - analogs & derivatives Cholecalciferol - chemical synthesis Cholecalciferol - chemistry Cholecalciferol - pharmacology Indicators and Reagents Intestines Membrane Potentials - drug effects Membrane Potentials - physiology Mice Models, Molecular Molecular Conformation Molecular Structure Osteoblasts - drug effects Osteoblasts - metabolism Receptors, Calcitriol - metabolism Signal Transduction Space life sciences Transcription, Genetic - drug effects
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Beschreibung
Zusammenfassung:	Separation of genomic and nongenomic vitamin D activities was achieved by structural modification of 1,25-dihydroxy vitamin D3 by introduction of 16 and 23E double bonds. The modified compound 3, lacking a 1 alpha-hydroxy group, exhibits only nongenomic activity. Its 1 alpha-hydroxy relative 4 expresses fully both genomic and non-genomic activities. A total synthesis of analogues 3 and 4 is described.
ISSN:	0968-0896
DOI:	10.1016/S0968-0896(98)00164-3