Synthesis and biological activity of 22-oxa CD-ring modified analogues of 1α,25-dihydroxyvitamin D3: Spiro[5.5]undecane CF-ring analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 15, 2004, Pages 3889-3892

  Schepens, Wim ^a   Van Haver, Dirk ^a   Vandewalle, Maurits ^a   De Clercq, Pierre J ^a   Bouillon, Roger ^b   Verstuyf, Annemieke ^b  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CALCITRIOL DERIVATIVE; VITAMIN D RECEPTOR;

ARTICLE; BINDING AFFINITY; CHEMICAL MODEL; CIRCULAR DICHROISM; DRUG ACTIVITY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; GENOMICS;

CALCITRIOL; GENE EXPRESSION REGULATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 3042594206     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.05.058     Document Type: Article

References (21)

1. Vitamin D; Feldman, D., Glorieux, F. H., Eds.; Academic Press: San Diego, USA, 1997; 1285 pp
2. Proceedings of the Eleventh Workshop on Vitamin D; Norman, A. W., Bouillon, R., Thomasset, M., Eds.; University of California: Riverside, USA, 2000; pp 1-992, and the previous 10 volumes in this series
3. Bouillon R., Okamura W.H., Norman A.W. Endocr. Rev. 16:1995;200-257
4. Murayama E., Miyamoto K., Kubodera M., Mori T., Matsunaga I. Chem. Pharm. Bull. (Tokyo). 34:1986;4410-4413
5. Abe J., Morikawa M., Miyamoto K., Kaiko S., Fukushima M., Miyaura C., Abe E., Suda T., Nishii Y. FEBS Lett. 226:1987;58-62
6. Nishii Y., Okano T. Steroids. 66:2001;137-146
7. Binderup L., Latini S., Binderup E., Bretting C., Calverley M., Hansen K. Biochem. Pharmacol. 42:1991;1569-1575
8. Perlman K.L., Sicinski R.R., Schnoes H.K., DeLuca H.F. Tetrahedron Lett. 31:1990;1823-1824
9. Bouillon R.; De Clercq P.; Pirson P.; Vandewalle M. Novel Structural Analogues of Vitamin D, Patent PCT/EP 93, 202037, 3, 1993; Chem. Abstr. 1996, 122, 314933m
10. Zhu G.-D., Okamura W.H. Chem. Rev. 95:1995;1877-1952
11. Posner G.H., Kahraman M. Eur. J. Org. Chem. 2000;3889-3895
12. Sabbe K., D'Halleweyn C., De Clercq P., Vandewalle M., Bouillon R., Verstuyf A. Bioorg. Med. Chem. Lett. 6:1996;1697-1702
13. Chen Y.-J., Gao L.J., Murad I., Verstuyf A., Verlinden L., Verboven C., Bouillon R., Viterbo D., Milanesio M., Van Haver D., Vandewalle M., De Clercq P.J. Org. Biomol. Chem. 1:2003;257-267. and references cited therein.
14. 3 analogues with an intact D-ring, but a connection between positions 18 and 20, see: Cornella I., Pérez Sestelo J., Mouriño A., Sarandeses L.A. J. Org. Chem. 67:2002;4707-4714
15. Varela C., Nilsson K., Torneiro M., Mouriño A. Helv. Chim. Acta. 85:2002;3251-3261
16. Harding K.E., Cooper J.L., Puckett P.M. J. Org. Chem. 44:1979;2834-2838
17. Kociensky P.J., Lythgoe B., Waterhouse I. J. Chem. Soc., Perkin Trans. 1. 1980;1045-1050
18. Perlman K.L., Swenson R.E., Paaren H.E., Schnoes H.K., DeLuca H.F. Tetrahedron Lett. 32:1991;7663-7666
19. Baggiolini E.G., Iacobelli J.A., Hennesy B.M., Uskokovic M.R. J. Am. Chem. Soc. 104:1982;2945-2948
20. 3, rt). Starting from the vitamin as well as the previtamin the same equilibrium composition was reached and was found to be in favour of previtamin 18a (25:75), but the equilibration was very slow (about 90 days starting from 4a)
21. 3) δ 5.87 (AB, J=12.4 Hz, 1H), 5.70 (AB, J=12.4 Hz, 1H), 5.64 (br s, 1H), 4.19 (br s, 1H), 4.14-4.09 (m, 1H), 3.79 (br s, 1H), 3.70 (t, J=5.7 Hz, 2H), 3.32 (tt, J=8.0, 4.0 Hz, 1H), 2.44 (dd, J=16.7, 4.7 Hz, 1H), 2.08-2.03 (m, 3H), 1.86 (AB, J=16.9 Hz, 1H), 1.82 (AB, J=16.9 Hz, 1H), 1.72 (s, 3H), 1.76-1.41 (m, 14H), 1.24 (s, 6H), 1.14-0.90 (m, 2H) ppm