A concise and efficient route to 2α-(ω-hydroxyalkoxy)-1α,25-dihydroxyvitamin D3: Remarkably high affinity to vitamin D receptor

Organic Letters

Volumn 2, Issue 17, 2000, Pages 2619-2622

  Kittaka, Atsushi ^a   Suhara, Yoshitomo ^a   Takayanagi, Hitoshi ^a   Fujishima, Toshie ^a   Kurihara, Masaaki ^b   Takayama, Hiroaki ^a  

^a TEIKYO UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CALCITRIOL; CALCITRIOL RECEPTOR; DRUG DERIVATIVE; PALLADIUM;

ANIMAL; ARTICLE; CATTLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; IN VITRO STUDY; METABOLISM; STEREOISOMERISM; SYNTHESIS; THYMUS;

ANIMALS; CALCITRIOL; CATTLE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PALLADIUM; RECEPTORS, CALCITRIOL; STEREOISOMERISM; THYMUS GLAND;

EID: 0034710456     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006222j     Document Type: Article

References (32)

1. This paper is dedicated (by A.K.) to Prof. Dr. A. Eschenmoser on the occasion of his 75th birthday.
2. (a) Vitamin D; Feldman, D., Glorieux, F. H., Pike, J. W., Eds.; Academic Press: New York, 1997.
3. (b) Ettinger, R. A.; DeLuca, H. F. Adv. Drug Res. 1996, 28, 269-312.
4. Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr. Rev. 1995, 16, 200-257.
5. (a) Miyamoto, K.; Murayama, E.; Ochi, K.; Watanabe, H.; Kubodera, N. Chem. Pharm. Bull. 1993, 41, 1111-1113.
6. (b) Hatakeyama, S.; Ikeda, T.; Maeyama, J.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawase, A.; Kubodera, N. Bioorg. Med. Chem. Lett. 1997, 7, 2871-2874.
7. (c) Moriarty, R. M.; Brumer, H. Tetrahedron Lett. 1995, 36, 9265-9268.
8. (d) Takahashi, T.; Nakazawa, M. Synlett 1993, 37-39.
9. (e) Takahashi, T.; Nakazawa, M.; Sakamoto, Y.; Houk, K. N. Tetrahedron Lett. 1993, 34, 4075-4078.
10. For biological activities of a series of 2β-substituted analogues, see: (f) Tsugawa, N.; Nakagawa, K.; Kurobe, M.; Ono, Y.; Kubodera, N.; Ozono, K.; Okano, T. Biol. Pharm. Bull. 2000, 23, 66-71.
11. Syntheses of 19-nor and 2-(4-hydroxybutyl) analogues of ED-71 were reported, see: (g) Sicinski, R. F.; Perlman, K. L.; DeLuca, H. F. J. Med. Chem. 1994, 37, 3730-3738.
12. (h) Posner, G. H.; Johnson, N. J. Org. Chem. 1994, 59, 7855-7861.
13. (a) Konno, K.; Maki, S.; Fujishima, T.; Liu, Z.-P.; Miura, D.; Chokki, M.; Takayama, H. Bioorg. Med. Chem. Lett. 1998, 8, 151-156.
14. (b) Nakagawa, K.; Kurobe, M.; Ozono, K.; Konno, K.; Fujishima, T.; Takayama, H.; Okano, T. Biochem. Pharmcol. 2000, 59, 691-702.
15. Suhara, Y.; Nihei, K.; Tanigawa, H.; Fujishima, T.; Konno, K.; Nakagawa, K.; Okano, T.; Takayama, H. Bioorg. Med. Chem. Lett. 2000, 10, 1129-1132.
16. (a) Umesono, K.; Murakami, K. K.; Thompson, C. C.; Evans, R. M. Cell 1991, 65, 1255-1266.
17. (b) DeLuca, H. F.; Zierold, C. Nutr. Rev. 1998, 56, 54-75.
18. (c) Takeyama, K.; Masuhiro, Y.; Fuse, H.; Endoh, H.; Murayama, A.; Kitanaka, S.; Suzawa, M.; Yanagisawa, J.; Kato, S. Mol. Cell. Biol. 1999, 19, 1049-1055.
19. (d) Yanagisawa, J.; Yanagi, Y.; Masuhiro, Y.; Suzawa, M.; Watanabe, M.; Kashiwagi, K.; Toriyabe T.; Kawabata, M.; Miyazono, K.; Kato, S. Science 1999, 283, 1317-1321.
20. Wiggins, L. S. Methods Carbohydr. Chem. 1963, 2, 188-191.
21. Beau, J.-M.; Aburaki, S.; Pougny, J.-R.; Sinay, P. J. Am. Chem. Soc. 1983, 105, 621-622.
22. (a) Hanessian, S. Methods Carbohydr. Chem. 1972, 6, 183-189.
23. (b) Hanessian, S.; Plessas, N. R. J. Org. Chem. 1969, 34, 1035-1044.
24. In the case of n = 1, recovered 9 (23%) and a mixture of diols (15%), which could be quantitatively recycled to the tris-O-TBDMS derivative 9, were obtained. Then, the recovered 9 and the recycled 9 were combined and desilylated again. Overall yield of 10 for these three steps was 72%. For n = 0 and 2, this recycled step was also applied and overall yields were noted in Scheme 1.
25. (a) Bernotas, R. C.; Pezzone, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305-311.
26. (b) Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990-2016.
27. Trost, B. M.; Dumas, J.; Villa, M. J. Am. Chem. Soc. 1992, 114, 9836-9845.
28. Imae, Y.; Manaka, A.; Yoshida, N.; Ishimi, Y.; Shinki, T.; Abe, E.; Suda, T.; Konno, K.; Takayama, H.; Yamada, S. Biochim. Biophys. Acta 1994, 1213, 302-308.
29. (a) Rochel, N.; Wultz, J. M.; Mitschler, A.; Klaholz, B.; Moras, D. Mol. Cell 2000, 5, 173-179.
30. (b) Yamamoto, K.; Masuno, H.; Choi, M.; Nakashima, K.; Taga, T.; Ooizumi, H.; Umesono, K.; Sicinska, W.; VanHooke, J.; DeLuca, H. F.; Yamada, S. PNAS 2000, 97, 1467-1472.
31. (c) Norman, A. W.; Adams, D.; Collins, E. D.; Okamura, W. H.; Fletterick, R. J. J. Cell. Biochem. 1999, 74, 323-333.
32. Calculated by MacroModel ver. 6.5 (Schrodinger, Inc.) on a SGI O2 Workstation. The C17 steroidal side chain was omitted for the calculation.