The synthesis of CD-ring modified 1α,25-dihydroxy vitamin D analogues: Six-membered D-ring analogues II

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 11, 1997, Pages 1465-1468

  Linclau, B ^a   De Clercq, P ^a   Vandewalle, M ^a   Bouillon, R ^b   Verstuyf, A ^b  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CALCITRIOL DERIVATIVE; VITAMIN D RECEPTOR;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CELL DIFFERENTIATION; CELL PROLIFERATION; CONFORMATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; REACTION ANALYSIS; SWINE;

EID: 0031007933     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00243-6     Document Type: Article

References (22)

1. Bouillon, R.; Van Baden, H. Saudi Med. J. 1989, 10, 260.
2. DeLuca, H.F.; Burmester, J.; Darwish, H.; Krisinger, J. Comprehensive Medicinal Chemistry, Pergamon Press, New York 1990, vol. 3, 1129.
3. Bouillon, R.; Okamura, W.H.; Norman, A.W. Endocrine Reviews 1995, 16, 200.
4. (a) Bouillon, R.; De Clercq, P.; Pirson, P.; Vandewalle, M. Novel structural analogues of vitamin D; patent PCT/EP 93.202037.3; priority date 09-07-1993;
5. (b) Sabbe, K.; D'Halleweyn, C.; De Clercq, P.; Vandewalle, M.; Bouillon, R.; Verstuyf, A. Bioorg. Med. Chem. Lett. 1996, 6, 1697;
6. (c) Gui-Dong, Zhu; Yongjun, Chen; Xiaoming, Zhou; Vandewalle, M.; De Clercq, P.; Bouillon, R.; Verstuyf, A. Bioorg. Med. Chem. Lett. 1996, 6, 1703;
7. (d) For an analogous approach see Kutner, A.; Zhao, H.; Fitak, H.; Wilson, S.R. Biorganic Chem. 1995,23, 22.
8. Linclau, B.; De Clercq, P.; Vandewalle, M.; Bouillon, R.; Verstuyf, A. Biorg. Med. Chem. Lett. 1997 proceeding paper.
9. (a) Uskokovic, M.R.; Baggiolini, E.; Shiuey, S.J.; Iacobelli, J.; Hennessy, B.; Kiegiel, J.; Daniewski, A.R.; Pizzolato, G.; Courtney, L.F.; Horst, R.L.; Vitamin D Gene Regulation, Structure-Function Analysis and Clinical Application. Berlin : Walter de Gruyter, 1991, 139;
10. (b) Chen, T.C.; Persons, K.; Uskokovic, M.R.; Horst, R.L.; Holick, M.F. J. Nutr. Biochem. 1993, 4, 49.
11. Chapuis, C.; Brauchli, R. Helv. Chim. Acta 1992, 75, 1527.
12. Dauben, W.G.; Brookhart, T. J. Am. Chem. Soc. 1981, 703, 1293; Schmuff, N.R.; Trost, B.M. J. Org. Chem. 1983, 48, 1404; Ibuka, T.; Taga, T.; Nishii, S.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1988, 342.
13. Dauben, W.G.; Brookhart, T. J. Am. Chem. Soc. 1981, 703, 1293; Schmuff, N.R.; Trost, B.M. J. Org. Chem. 1983, 48, 1404; Ibuka, T.; Taga, T.; Nishii, S.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1988, 342.
14. Dauben, W.G.; Brookhart, T. J. Am. Chem. Soc. 1981, 703, 1293; Schmuff, N.R.; Trost, B.M. J. Org. Chem. 1983, 48, 1404; Ibuka, T.; Taga, T.; Nishii, S.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1988, 342.
15. Danheiser, R.L.; Nowick, J.S. J. Org. Chem. 1991, 56, 1176.
16. Black, T.H.; Eisenbeis, S.A.; McDermott, T.S.; Maluleka, S.L. Tetrahedron, 1990, 46, 2307.
17. Wu, W.-L.; Wu Y.-L. J. Org. Chem. 1993, 58, 3586.
18. Lythgoe, B.; Moran, T.A.; Nambudiry, M.E.N.; Tideswell, J.; Wright, P.W. J. Chem. Soc., Perkin Trans I 1978, 580; Kocienski, P.J.; Lythgoe, B. J. Chem. Soc., Perkin Trans. I 1978, 1290.
19. Lythgoe, B.; Moran, T.A.; Nambudiry, M.E.N.; Tideswell, J.; Wright, P.W. J. Chem. Soc., Perkin Trans I 1978, 580; Kocienski, P.J.; Lythgoe, B. J. Chem. Soc., Perkin Trans. I 1978, 1290.
20. Baggiolini, E.G.; Iacobelli, J.A.; Hennessy, B.M.; Batcho, A.D.; Sereno, J.F.; Uskokovic, M.R. J.Org. Chem. 1986, 51, 3098.
21. Binderup, L.; Latini, S.; Binderup, E.; Bretting, C.; Calverley, M.; Hansen, K. Biochem. Pharmacol. 1991, 42, 1569.
22. Bouillon, R.; Allewaert, K.; Van Leeuwen, J.P.T.M.; Tan, B.K.; Xiang, D.Z.; De Clercq, P.; Vandewalle, M.; Pols, H.A.P.; Bos, M.P.; Van Baelen, H.; Birken häger, J.C. J. Biol. Chem. 1992, 267, 3044.