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

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 11, 1997, Pages 1461-1464

  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; ARTICLE; BINDING AFFINITY; CALCIUM BLOOD LEVEL; CELL DIFFERENTIATION; CELL PROLIFERATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; NORMAL HUMAN; REACTION ANALYSIS;

EID: 0030925585     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00242-4     Document Type: Article

References (20)

1. Bouillon, R.; Van Baelen, 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. Bioorganic Chem. 1995, 23, 22.
8. Binderup, L.; Latini, S.; Binderup, E.; Bretting, C.; Calverley, M.; Hansen, K. Biochem. Pharmacol. 1991, 42, 1569.
9. Chapuis, C.; Brauchli, R. Helv. Chim. Acta 1992, 75, 1527.
10. 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.
11. 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.
12. Baggiolini, E.G.; Iacobelli, J.A.; Hennessy, B.M.; Batcho, A.D.; Sereno, J.F.; Uskokovic, M.R. J. Org. Chem. 1996, 57, 3098.
13. Wicha, J.; Bal, K. J. Chem. Soc., Perkins Trans, I 1978, 1282.
14. Lindau, B.; Vandewalle, M.; Syntlett 1995, 10, 1063.
15. Still, W.C; Mohamadi, F.; Richards, N.G.J.; Guida, W.C.; Lipton, M.; Liskang, R.; Chang, G.; Hendrickson, T., De Gunst, F.; Hasel, W.; MacroModel V3.0, Department of Chemistry, Colombia University, New York, NY 10027, USA.
16. Marshall, J.A.; Garofalo, A.W. J. Org. Chem. 1993, 58, 3675.
17. Corey, E.J.; Chaykovski, M. J. Am. Chem. Soc. 1965, 87, 1353.
18. 1H-NMR (500 MHz) : J value for 14-H (after double irradiation of 8-H); 13, m (Δ J = 10Hz); 14, 12.52 and 3.72 Hz; 21, 12.40 and 3.78 Hz; 27, 12.47 and 3.84 Hz; 28, m (Δ J = 10Hz).
19. Lipshutz, B.H.; Harvey, D.F. Synth. Commun. 1982, 72, 267.
20. 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.; Birkenhäger, J.C. J. Biol. Chem. 1992, 267, 3044.