Design and synthesis of a 1α,25-dihydroxyvitamin D3 dimer as a potential chemical inducer of vitamin D receptor dimerization

Organic Letters

Volumn 1, Issue 7, 1999, Pages 1005-1007

  Sestelo, José Pérez ^a   Mouriño, Antonio ^b   Sarandeses, Luis A ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CALCITRIOL; CALCITRIOL RECEPTOR;

ARTICLE; CHEMISTRY; DIMERIZATION; METABOLISM; PROTEIN BINDING; SYNTHESIS;

CALCITRIOL; DIMERIZATION; PROTEIN BINDING; RECEPTORS, CALCITRIOL;

EID: 0008166622     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990878z     Document Type: Article

References (19)

1. 3 (1b) by two specific enzymatic hydroxylations.
2. For a general review of vitamin D chemistry and biology, see: (a) Vitamin D: Chemistry, Biology and Clinical Applications of the Steroid Hormone; Norman, A. W., Bouillon, R., Thomasset, M., Eds; Vitamin D Workshop, Inc.: Riverside, CA, 1997.
3. (b) Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877.
4. Freedman, L. P.; Lemon, B. D. In Vitamin D; Feldman, D., Glorieux, F. H., Pike, J. W., Eds.; Academic Press: San Diego, 1997; Chapter 9, pp 127-148.
5. (a) Driver, S. T.; Schreiber, S. L. J. Am. Chem. Soc. 1997, 119, 5106.
6. (b) Ho, S. N.; Biggar, S. R.; Spencer, D. M.; Schreiber, S. L.; Crabtree, G. R. Nature 1996, 382, 822.
7. Spencer, D. M.; Wandless, T. J.; Schreiber, S. L.; Crabtree, G. R. Science 1993, 262, 1019.
8. (a) Pruschy, M. N.; Spencer, D. M.; Kapoor, T. M.; Miyaki, H.; Crabtree, G. R.; Schreiber, S. L. Chem. Biol. 1994, 1, 163.
9. (b) Beishaw, P. J.; Spencer, D. M.; Crabtree, G. R.; Schreiber, S. L. Chem. Biol. 1996, 3, 731.
10. Calverley, M. J.; Jones, J. In Antitumor Steroids; Blickenstaff, R. T., Ed.; Academic Press: San Diego, 1992; Chapter 7, pp 193-270.
11. Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocrine Rev. 1995, 16, 200.
12. Olefin metathesis has proved to be useful for homodimerization, see: Clark, T. D.; Gadhiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364 and ref 4a.
13. Lythgoe, B.; Moran, T. A.; Nambudiry, M. E. N.; Ruston, S.; Tideswell, J.; Wright, P. W. Tetrahedron Lett. 1975, 3863.
14. (a) Torneiro, M.; Fall, Y.; Castedo, L.; Mourino, A. Tetrahedron Lett. 1992, 33, 105.
15. (b) D'Halleweyn, C.; Van Haver, D.; Van der Eycken, J.; De Clerq, P.; Vandewalle, M. Bioorg. Med. Chem. Lett. 1992, 2, 477.
16. Mascareñas, J. L.; Pérez Sestelo, J.; Castedo, L.; Mouriño, A. Tetrahedron Lett. 1991, 32, 2813.
17. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
18. Mouriño, A.; Torneiro, M.; Vitale, C.; Fernández, S.; Pérez Sestelo, J.; Anné, S.; Gregorio, C. Tetrahedron Lett. 1997, 38, 4713.
19. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.