6-s-cis locked analogues of the steroid hormone 1α,25-dihydroxyvitamin D3. Synthesis of novel A-ring stereoisomeric 1,25-dihydroxy-3-epi-19-nor-previtamin D3 derivatives

Journal of Organic Chemistry

Volumn 65, Issue 18, 2000, Pages 5647-5652

  Díaz, Mónica ^a   Ferrero, Miguel ^a   Fernández, Susana ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1ALPHA,25 DIHYDROXY 3 EPI 19 NORPREVITAMIN D3; 1BETA,25 DIHYDROXY 3 EPI 19 NORPREVITAMIN D3; CALCITRIOL DERIVATIVE; STEROID HORMONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOISOMERISM; STEREOSPECIFICITY;

CALCITRIOL; CHOLECALCIFEROL; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY;

EID: 0041705664     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000443l     Document Type: Article

References (32)

1. (a) Lowe, K. E.; Maiyar, A. C.; Norman, A. W. Crit. Rev. Eukar. Gene Exp. 1992, 2, 65.
2. (b) Pike, J. W. Annu. Rev. Nutr. 1991, 11, 189-216.
3. (c) Norman, A. W., Bouillon, R., Thomasset, M., Eds. Vitamin D: Gene Regulation, Structure-Function Analysis and Clinical Application; Walter de Gruyter: Berlin, 1991.
4. (d) Norman, A. W. Vitamin D: The calcium Homeostatic Steroid Hormone; Academic Press: New York, 1979.
5. (a) Norman, A. W., Bouillon, R., Thomasset, M., Eds. Vitamin D, A Pluripotent Steroid Hormone: Structural Studies, Molecular Endocrinology, and Clinical Applications; Walter de Gruyter: Berlin, 1994.
6. (b) Uskokovic, M. R. Bioorg. Med. Chem. Lett. 1993, 3, 1783-1896.
7. (a) Norman, A. W.; Nemere, I.; Zhou, L. X.; Bishop, J. E.; Lowe, K. E.; Maiyar, A. C.; Collins, E. D.; Taoka, T.; Sergeev, I.; Farach-Carson, M. C. J. Steroid Biochem. Mol. Biol. 1992, 41, 231-240.
8. (b) Deboland, A. R.; Nemere, I.; Norman, A. W. Biochem. Biophys. Res. Commun. 1990, 166, 217-222.
9. (a) Nemere, I.; Norman A. W. Endocrinology 1986, 119, 1406-1408.
10. (b) Nemere, I.; Yoshimoto, Y.; Norman A. W. Endocrinology 1984, 115, 1476-1483.
11. (a) Ettinger, R. A.; DeLuca, H. F. Adv. Drug. Res. 1996, 28, 269-312.
12. (b) Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocrine Rev. 1995, 16, 200-257.
13. Curtin, M. L.; Okamura, W. H. J. Am. Chem. Soc. 1991, 113, 6958-6966.
14. Norman, A. W.; Okamura, W. H.; Farach-Carson, M. C.; Allewaert, K.; Branisteanu, D.; Nemere, I.; Muralidharan, K. R.; Bouillon, R. J. Biol. Chem. 1993, 268, 13811-13819.
15. Okamura, W. H.; Midland, M. M.; Norman, A. W.; Hammond, M. W.; Dormanen, M. C.; Nemere, I. Ann. N.Y. Acad. Sci. 1995, 761, 344-348.
16. (a) Okamura, W. H.; Midland, M. M.; Hammond, M. W.; Rahman, N. A.; Dormanen, M. C.; Nemere, I.; Norman, A. W. J. Steroid Biochem. Mol. Biol. 1995, 53, 603-613.
17. (b) Dormanen, M. C.; Bishop, J. E.; Hammond, M. W.; Okamura, W. H.; Nemere, I.; Norman, A. W. Biochem. Biophys. Res. Commun. 1994, 201, 394-401.
18. (a) Díaz, M.; Ferrero, M.; Fernández, S.; Gotor, V. Tetrahedron Lett. 2000, 41, 775-779.
19. (b) Ferrero, M.; Fernández, S.; Gotor, V. J. Org. Chem. 1997, 62, 4358-4363.
20. (c) Fernández, S.; Díaz, M.; Ferrero, M.; Gotor, V. Tetrahedron Lett. 1997, 38, 5225-5228.
21. (d) Fernández, S.; Ferrero, M.; Gotor, V.; Okamura, W. H. J. Org. Chem. 1995, 60, 6057-6061.
22. Thompson, S. H. J.; Mahon, M. F.; Molloy, K. C.; Hadley, M. S.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1995, 379-383.
23. Barton, D. H. R.; Motherwell, W. B. Pure Appl. Chem. 1981, 53, 15-31.
24. Sarandeses, L. A.; Mascareñas, J. L.; Castedo, L.; Mouriño, A. Tetrahedron Lett. 1992, 33, 5445-5448.
25. (a) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127-164.
26. (b) Mitsunobu, O. Synthesis 1981, 1-28.
27. (a) Mascareñas, J. L.; Sarandeses, L. A.; Castedo, L.; Mouriño, A. Tetrahedron 1991, 47, 3485-3498.
28. (b) Barrack, S. A.; Gibbs, R. A.; Okamura, W. H. J. Org. Chem. 1988, 53, 1790-1796.
29. (a) Maynard, D. F.; Trankle, W. G.; Norman, A. W.; Okamura, W. H. J. Med. Chem. 1994, 37, 2387-2393.
30. (b) Also see refs 6, 10a, and 15b.
31. Inhoffen, H. H.; Quinkert, G.; Schüzt, S.; Kampe, D.; Domagk, G. F. Chem. Ber. 1957, 90, 664-673.
32. 13C NMR spectra in the Supporting Information.