Synthesis of CD-ring modified 1α,25-dihydroxy vitamin D analogues: C-ring analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 14, 1996, Pages 1703-1708

  Zhu, Gui Dong ^a   Chen, Yongjun ^a   Zhou, Xiaoming ^a   Vandewalle, Maurits ^a   De Clercq, Pierre J ^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; VITAMIN D BINDING PROTEIN; VITAMIN D DERIVATIVE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CALCIUM BLOOD LEVEL; CELL PROLIFERATION; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INTESTINE; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SWINE;

ANIMALIA; SUS SCROFA;

EID: 0030598677     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00301-0     Document Type: Article

References (29)

1. 1. Bouillon, R.; Van Baelen, H. Saudi Med. J. 1989, 10, 260.
2. 2. DeLuca, H.F.; Burmester, J.; Darwish, H.; Krisinger, J. Comprehensive Medicinal Chemistry, Pergamon Press, New York 1990, vol. 3, 1129.
3. 3. Bouillon, R.; Okamura, W.H.; Norman, A.W. Endocrine Reviews 1995, 76, 200.
4. 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) A similar concept was reported by A. Kutner at the 9th Vitamin D Workshop, Orlando, USA (28/04 - 02/05 1994). See Kutner, A.; Wilson, S.R.; Zhao, H.; Fitak, H. Chodymski, H.; Halkes, S.J. Polish Patent Appl. No P302010, 1994.
6. (b) A similar concept was reported by A. Kutner at the 9th Vitamin D Workshop, Orlando, USA (28/04 - 02/05 1994). See Kutner, A.; Wilson, S.R.; Zhao, H.; Fitak, H. Chodymski, H.; Halkes, S.J. Polish Patent Appl. No P302010, 1994.
7. 5. For the synthesis of "E-ring" analogues, see : Sabbe, K.; D'Hallewyn, C.; De Clercq, P.; Vandewalle, M.; Bouillon, R.; Verstuyf, A. Bioorg. Med. Chem. Lett. 1996, 6, 1697.
8. 6. For a review, see : Norman, A. W. Vitamin D, the Calcium Homeostatic Steroid Hormone, Academic Press: New York, 1979; pp. 37. Havinga, E. Experientia 1973, 29, 1181.
9. 6. For a review, see : Norman, A. W. Vitamin D, the Calcium Homeostatic Steroid Hormone, Academic Press: New York, 1979; pp. 37. Havinga, E. Experientia 1973, 29, 1181.
10. 7. Grieco, P.A.; Yokoyama, Y.; Gilman, S.; Ohfune, Y. J. Chem. Soc. 1977, 870. 8. Chapleo, C. B.; Hallett, P.; Lythgoe, B.; Waterhouse, I.; Wright, P. W. J. Chem. Soc. Perkin I, 1977, 1211.
11. 7. Grieco, P.A.; Yokoyama, Y.; Gilman, S.; Ohfune, Y. J. Chem. Soc. 1977, 870. 8. Chapleo, C. B.; Hallett, P.; Lythgoe, B.; Waterhouse, I.; Wright, P. W. J. Chem. Soc. Perkin I, 1977, 1211.
12. 9. Ireland, R. E.; Wipf, P.; Jia-Ning Xiang J. Org. Chem. 1991, 56, 3572.
13. 10. Lythgoe, B.; Moran, T.A.; Nambudiry, M.E.N.; Tideswell, J.; Wright, P.W. J. Chem. Soc., Perkin Trans I 1978, 590; Kocienski, P.J.; Lythgoe, V. J. Chem. Soc., Perkin Trans. I 1978, 1290.
14. 10. Lythgoe, B.; Moran, T.A.; Nambudiry, M.E.N.; Tideswell, J.; Wright, P.W. J. Chem. Soc., Perkin Trans I 1978, 590; Kocienski, P.J.; Lythgoe, V. J. Chem. Soc., Perkin Trans. I 1978, 1290.
15. 11. Baggiolini, E.G.; Iacobelli, J.A.; Hennessy, B.M.; Batcho, A.D.; Sereno, J.F.; Uskokovic, M.R. J. Org. Chem. 1986, 51, 3098.
16. 12. (a) Perlman, K.L.; Sicinski, R.R.; Schnoes, H.K.; DeLuca, H.F. Tetrahedron Lett. 1990, 31, 1823;
17. (b) Perlman, K.L.; Swenson, R.E.; Paaren, H.E.; Schnoes, H.K.; DeLuca, H.F. Tetrahedron Lett. 1991, 32, 7663.
18. 13. Corey, E. J. J. Am. Chem. Soc. 1972, 94, 6190; also see : Roush, W. R.; Palkowitz, A. D.; Palmer, M. A. J. Org. Chem. 1987, 52, 316.
19. 13. Corey, E. J. J. Am. Chem. Soc. 1972, 94, 6190; also see : Roush, W. R.; Palkowitz, A. D.; Palmer, M. A. J. Org. Chem. 1987, 52, 316.
20. 14. Gilbert, J. C.; Weerasooriya, U. J. Org. Chem., 1979, 44, 4997.
21. 15. Lipshutz, B. H.; Wilhelm, R. S.; Kozlowki, J. Tetrahedron Lett. 1982, 23, 3755; Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. J. Org. Chem. 1984, 48, 3938.
22. 15. Lipshutz, B. H.; Wilhelm, R. S.; Kozlowki, J. Tetrahedron Lett. 1982, 23, 3755; Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. J. Org. Chem. 1984, 48, 3938.
23. 16. Noyori, R.; Suzuki, M.; Kawagishi, T. Tetrahedron Lett. 1980, 21, 1249; Hooz, J.; Layton, R. B. Can. J. Chem. 1970, 48, 1626.
24. 16. Noyori, R.; Suzuki, M.; Kawagishi, T. Tetrahedron Lett. 1980, 21, 1249; Hooz, J.; Layton, R. B. Can. J. Chem. 1970, 48, 1626.
25. 17. Magnus, P.; Quaglioto, D. J. Org. Chem. 1985, 50, 1621; Magnus, P. private communication.
26. 17. Magnus, P.; Quaglioto, D. J. Org. Chem. 1985, 50, 1621; Magnus, P. private communication.
27. 18. Semmelhack, M. F.; Yamashita, A.; Tomesch, J. C.; Hirotsu, K. J. Am. Chem. Soc. 1978, 100, 5565.
28. 19. Pérez-Sestelo, J.; Mascareñas, J.L.; Mouriño, A. Tetrahedron Lett. 1994, 275.
29. 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.