Structure-activity relationship studies on vitamin D lactam derivatives as vitamin D receptor antagonist

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 15, 2008, Pages 4287-4290

  Cho, Kaori ^a   Uneuchi, Fumito ^a   Kato Nakamura, Yuko ^b   Namekawa, Jun ichi ^b   Ishizuka, Seiichi ^b   Takenouchi, Kazuya ^b   Nagasawa, Kazuo ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b TEIJIN LTD   (Japan)

Author keywords

Antagonist; DLAM; SAR; Vitamin D; Vitamin D receptor

Indexed keywords

CALCITRIOL; FUNCTIONAL GROUP; LACTAM DERIVATIVE; PHENYL GROUP; PROTEIN INHIBITOR; VITAMIN D RECEPTOR;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG BINDING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

CALCITRIOL; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; HUMANS; INHIBITORY CONCENTRATION 50; LACTAMS; MOLECULAR STRUCTURE; RECEPTORS, CALCITRIOL; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; VITAMIN D;

EID: 47849099038     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.06.095     Document Type: Article

References (28)

1. In: Feldman D., Glorieux F.H., and Pike J.W. (Eds). Vitamin D. 2nd ed. (2005), Academic Press, New York
2. Holick, M. F., Ed. Vitamin D Physiology, Molecular Biology and Clinical Applications; Humana Press: Totowa, NJ, 1999.
3. Bouillon R., Okamura W.H., and Norman A.W. Endocr. Rev. 16 (1995) 200
4. Mangelsdorf Ds.J., Thummel C., Beato M., Herrlich P., Schutz G., Umesono K., Blumgerg B., Kastner P., Mark M., Chambon P., and Evans R.M. Cell 83 (1995) 835
5. Björklund S., Almouzni G., Davidson I., and Nightingale K.P. Cell 96 (1999) 759
6. Brzozowski A.M., Pike A.C.W., Dauter Z., Hubbard R.D., Bonn T., Engström O., Öhman L., Greene G.L., Gustafsson J.-Å., and Carlquist M. Nature 389 (1997) 753
7. Carlberg C. J. Cell. Biochem. 88 (2003) 274
8. Miura D., Manabe K., Ozono K., Saito M., Gao Q., Norman A.W., and Ishizuka S. J. Biol. Chem. 274 (1999) 16392
9. Ozono K., Saito M., Miura D., Michigami T., Nakajima S., and Ishizuka S. J. Biol. Chem. 274 (1999) 32376
10. Takenouchi K., Sogawa R., Manabe K., Saitoh H., Gao Q., Miura D., and Ishizuka S. J. Steroid Biochem. Mol. Biol. 89-90 (2004) 31
11. Bula C.M., Bishop J.E., Ishizuka S., and Norman A.W. Mol. Endocrinol. 11 (2000) 1788
12. Ishizuka S., Miura D., Osono K., Chokki M., Mimura H., and Norman A.W. Endocrinol. 142 (2001) 59
13. Carlberg C. Mol. Pharmacol. 59 (2001) 1478
14. Saito N., Matsunaga T., Saito H., Anzai M., Takenouchi K., Miura D., Namekawa J., Ishizuka S., and Kittaka A. J. Med. Chem. 49 (2006) 7063
15. Herdick M., Steinmeyer A., and Carlberg C. J. Biol. Chem. 275 (2000) 16506
16. Herdick M., Steinmeyer A., and Carlberg C. Chem. Biol. 7 (2000) 885
17. Bury Y., Steinmeyer A., and Carlberg C. Mol. Pharmacol. 58 (2000) 1067
18. Väisänen S., Peräkylä M., Käsrkkäinen J.I., Steinmeyer A., and Carlberg C. J. Mol. Biol. 315 (2002) 229
19. Tocchini-Valentini G., Rochel N., Wurtz J.M., and Moras D. J. Med. Chem. 47 (2004) 1956
20. Igarashi M., Yoshimoto N., Yamamoto K., Shimizu M., Ishizawa M., Makishima M., DeLuca H.F., and Yamada S. Arch. Biochem. Biophys. 460 (2007) 240
21. Kato Y., Hashimoto Y., and Nagasawa K. Molecules 8 (2003) 488
22. Kato Y., Nakano Y., Sano H., Tanatani A., Kobayashi H., Shimazawa R., Koshino H., Hashimoto Y., and Nagasawa K. Bioorg. Med. Chem. Lett. 14 (2004) 2579
23. Nakano Y., Kato Y., Imai K., Ochiai E., Namekawa J., Ishizuka S., Takenouchi K., Tanatani A., Hashimoto Y., and Nagasawa K. J. Med. Chem. 49 (2006) 2398
24. 7c.
25. 3) δ 6.38-6.32 (m, 4H), 6.01 (d, J = 11.0 Hz, 1H), 5.33 (s, 1H), 4.99 (s, 1H), 4.90 (d, J = 14.9 Hz, 1H), 4.43 (br s, 1H), 4.23 (br s, 1H), 3.96-3.88 (m, 5H), 3.51 (m, 1H), 2.82 (dd, J = 12.1, 4.0 Hz, 1H), 2.60 (dd, J = 13.5, 3.3 Hz, 1H), 2.38-2.29 (m, 3H), 2.07-0.96 (m, 36H), 0.89 (d, J = 6.6 Hz, 3H), 0.50 (s, 3H).
26. Ishizuka S., Bannai K., Naruchi T., and Hashimoto Y. Steroids 37 (1981) 2715
27. Collins S.J., Ruscetti F.W., Gallagher R.E., and Gallo R.C. J. Exp. Med. 149 (1979) 969
28. 4b.