Synthesis and biological activities of 2α-chloro-1-epicalcitriol and 1- epicalcitriol

Steroids

Volumn 63, Issue 1, 1998, Pages 28-36

  Schönecker, Bruno ^a   Reichenbächer, Manfred ^a   Gliesing, Sabine ^a   Gonschior, Manuela ^a   Griebenow, Sirid ^a   Scheddin, Dietmar ^b   Mayer, Hubert ^b  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

Author keywords

A ring derivatives; Affinity studies; Diequatorial 1 ,2 epoxide cleavage; Vitamin D; Vitamin D binding protein; Vitamin D responsive element

Indexed keywords

1 EPICALCITRIOL; 2ALPHA CHLORO 1 EPICALCITRIOL; COLECALCIFEROL DERIVATIVE; UNCLASSIFIED DRUG; VITAMIN D BINDING PROTEIN; VITAMIN D RECEPTOR;

ADIPOCYTE; ANIMAL CELL; ARTICLE; BINDING AFFINITY; CALCIUM HOMEOSTASIS; CELL CULTURE; CELL DIFFERENTIATION; DNA SYNTHESIS; MOUSE; NONHUMAN; RECEPTOR BINDING; SYNTHESIS; TRANSCRIPTION REGULATION; VITAMIN D METABOLISM;

ADIPOCYTES; ANIMALS; CALCITRIOL; CELL COUNT; CELL DIFFERENTIATION; CELL DIVISION; CELL LINE; FIBROBLASTS; HUMANS; MICE; STEREOISOMERISM;

ANIMALIA; MURINAE;

EID: 0031962860     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(97)00106-2     Document Type: Article

References (25)

1. Itin PH, Pittelkow MR, Kumar R. Effects of vitamin D metabolites on proliferation and differentiation of cultured human epidermal keratinocytes grown in serum-free or defined culture medium. Endocrinology. 135:1994;1793-1798.
2. 3 regulation of growth, morphology, and fibronectin in a human osteosarcoma cell line. J Cell Phys. 123:1985;401-409.
3. 3 modulates bone marrow macrophage precursor proliferation and differentiation. J Biol Chem. 262:1987;15922-15929.
4. 3 induces differentiation of osteoclast-like cells from human bone marrow cultures. Biochem Biophys Res Commun. 176:1991;1189-1195.
5. 3, KH 1060. Endocrinology. 136:1995;866-872.
6. Okamura WH, Palenzuela JA, Plumet J, Midland MM. Vitamin D structure-function analyses and the design of analogs . J Cell Biochem. 49:1992;10-18.
7. Binderup L, Bramm E. Effects of a novel vitamin D analogue MC 903 on cell proliferation and differentiation in vitro and on calcium metabolism in vivo. Biochem Pharm. 37:1988;889-895.
8. 3 stimulated transcaltachia (the rapid hormonal stimulation of intestinal calcium transport). Biochem Biophys Res Commun. 189:1992;1450-1456.
9. 3. Stereocontrolled total synthesis via intramolecular and intermolecular Diels-Alder cycloadditions. Preliminary biological testing. J Org Chem. 60:1995;4617-4628.
10. Ahrens M, Ankenbauer T, Schröder D, Hollnagel A, Mayer H, Gross G. Expression of human bone morphogenetic proteins-2 or -4 in murine mesenchymal progenitor C3H10T 1 2 cells induced differentiation into distinct mesenchymal cell lineages. DNA Cell Biol. 12:1993;871-880.
11. 3. Steroids. 61:1996;598-608.
12. Wittmann S, Krieg R, Prousa R, Schönecker B, Droescher P. Transformation of (20S)-20-(hydroxymethyl)pregna-1,4-dien-3-one into (20S)-20-(p-toluenesulfonyloxymethyl)pregna-1,4-dien-3β-ol and -3α-ol, intermediates of vitamin D derivatives. J Prakt Chem. 338:1996;214-219.
13. 3. Bioorg Med Chem Lett. 3:1993;1849-1854.
14. Schönecker B, Droescher P, Adam G, Marquardt V, Walther D, Fischer R, Prousa R (1992). Ausgangsverbindungen zur Herstellung von Calcitriol sowie dessen Abkömmlingen, Verfahren zur Herstellung dieser Ausgangsverbindungen sowie Zwischenprodukte für dieses Verfahren. PCT/DE 92/00128. Chem Abstr (1993) 118:124879.
15. Reichenbächer M, Gliesing S, Lange C, Gonschior M, Schönecker B. Ein effektives Verfahren zur Herstellung von 1α,25-Dihydroxy-cholecalciferol (Calcitriol) aus 1α,3β,25-Trihydroxy-cholesta-5,7-dien (Procalcitriol). J Prakt Chem. 338:1996;634-641.
16. Reichenbächer M, Gliesing S, Hopf G. Eine verbesserte Apparatur für die Flash-Chromatographie. J Prakt Chem. 333:1991;779-784.
17. Ponsold K. Stickstoffhaltige Steroide, IV Darstellung von Azidohydrinen und vicinalen Aminoalkoholen aus Epoxysterinen . Chem Ber. 96:1963;1855-1864.
18. Glotter E, Krinsky P. Neighbouring group effects in the acid-catalysed opening of steroidal epoxides. J Chem Soc Perkin Trans 1. 1978;413-419.
19. 3. Chem Pharm Bull (Tokyo). 32:1984;3525-3531.
20. Eyley SC, Williams DH. Photolytic productions of vitamin D. The preparative value of a photo-sensitizer. J Chem Soc, Chem Commun. 1975;858.
21. 3. J Org Chem. 58:1993;1895-1899.
22. Thompson EB. Membrane transporters of steroid hormones. Curr Biol. 5:1995;730-732.
23. 3 and its analogs. J Bone Min Res. 9:1994;1277-1288.
24. Hulme EC, Birdsall NJM. Strategy and tactics in receptor-binding studies. Hulme EC. Receptor-Ligand Interactions A Practical Approach . 1992;63-176 IRL Press, Oxford, New York, Tokyo.
25. Okamura WH, Midland MM, Hammond MW, Rahman NA, Dormanen MC, Nemere I, Norman AW. Conformation and related topological features of Vitamin D: structure-function relationships. Norman AW, Bouillon R, Thomasset M. Vitamin D, a Pluripotent Steroid Hormone Structural, Molecular Endocrinology and Clinical Applications . 1994;12-19 Walter de Gruyter, Berlin, New York.