2-Substituted-16-ene-22-thia-1α,25-dihydroxy-26,27-dimethyl-19-norvitamin D3 analogs: Synthesis, biological evaluation, and crystal structure

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 14, 2008, Pages 6949-6964

  Shimizu, Masato ^a   Miyamoto, Yukiko ^a   Takaku, Hajime ^a   Matsuo, Mayumi ^a   Nakabayashi, Makoto ^a   Masuno, Hiroyuki ^a   Udagawa, Nobuyuki ^b   DeLuca, Hector F ^c   Ikura, Teikichi ^a   Ito, Nobutoshi ^a  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^b MATSUMOTO DENTAL UNIVERSITY   (Japan)

^c UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

16 Ene 22 thia 19 norvitamin D; Crystal structure; Structure activity relationships; Transcriptional activity; VDR binding affinity

Indexed keywords

1ALPHA,25 DIHYDROXY 2 (2 HYDROXYETHYLIDENE) 16 ENE 22 THIA 26,27 DIMETHYL 19,24 DINORVITAMIN D3; 1ALPHA,25 DIHYDROXY 2ALPHA(2 HYDROXYETHOXY) 16 ENE 22 THIA 24 HOMO 26,27 DIMETHYL 19 NORVITAMIN D3; 1ALPHA,25 DIHYDROXY 2ALPHA(2 HYDROXYETHOXY) 16 ENE 22 THIA 26,27 DIMETHYL 19 NORVITAMIN D3; 1ALPHA,25 DIHYDROXY 2ALPHA(2 HYDROXYETHOXY) 16 ENE 22 THIA 26,27 DIMETHYL 19,24 DINORVITAMIN D3; 1ALPHA,25 DIHYDROXY 2BETA(2 HYDROXYETHOXY) 16 ENE 22 THIA 24 HOMO 26,27 DIMETHYL 19 NORVITAMIN D3; 1ALPHA,25 DIHYDROXY 2BETA(2 HYDROXYETHOXY) 16 ENE 22 THIA 26,27 DIMETHYL 19 NORVITAMIN D3; 1ALPHA,25 DIHYDROXY 2BETA(2 HYDROXYETHOXY) 16 ENE 22 THIA 26,27 DIMETHYL 19,24 DINORVITAMIN D3; 1ALPHA,2ALPHA,25 TRIHYDROXY 2BETA METHYL 16 ENE 22 THIA 26,27 DIMETHYL 19,24 DINORVITAMIN D3 TERT BUTYLDIMETHYLSILYL ETHER; 1ALPHA,2BETA,25 TRIHYDROXY 2 ALPHA METHYL 16 ENE 22 THIA 26,27 DIMETHYL 19,24 DINORVITAMIN D3 TERT BUTYLDIMETHYLSILYL ETHER; COLECALCIFEROL DERIVATIVE; UNCLASSIFIED DRUG; VITAMIN D RECEPTOR;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HORMONE BINDING; HYDROGEN BOND; IN VITRO STUDY; LIGAND BINDING; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION; TRANSCRIPTION INITIATION;

AMINO ACIDS; ANIMALS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; HYDROPHOBICITY; PROTEIN CONFORMATION; RATS; RECEPTORS, CALCITRIOL; STRUCTURE-ACTIVITY RELATIONSHIP; VITAMIN D; WATER;

RATTUS; THIA;

EID: 47349130775     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.05.043     Document Type: Article

References (32)

1. In: Feldman D., lorrieux F.H., and Pike J.W. (Eds). Vitamin D (1997), Academic, New York
2. Abe E., Miyaura C., Sakagami H., Takeda M., Konno K., Yamazaki T., Yoshiki S., and Suda T. Proc. Natl. Acad. Sci. U.S.A. 78 (1981) 4990
3. Yamada S., Shimizu M., and Yamamoto K. Med. Res. Rev. 23 (2003) 89
4. Perlman K.L., Sicinski R.R., Schnoes H.K., and DeLuca H.F. Tetrahedron Lett. 31 (1990) 1823
5. Perlman K.L., Swenson R.E., Paaren H.E., Schnoes H.K., and DeLuca H.F. Tetrahedron Lett. 32 (1991) 7663
6. Sicinski R.R., Prahl J.M., Smith C.M., and DeLuca H.F. J. Med. Chem. 41 (1998) 4662
7. Shevde N.K., Plum L.A., Clagett-Dame M., Yamamoto H., Pike J.W., and DeLuca H.F. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 13487
8. Vanhooke J.L., Benning M.M., Bauer C.B., Pike J.W., and DeLuca H.F. Biochemistry 43 (2004) 4101
9. Takaku H., Miyamoto Y., Asami S., Shimazaki M., Yamada S., Yamamoto K., Udagawa N., DeLuca H.F., and Shimizu M. Bioorg. Med. Chem. 16 (2008) 1796
10. Shimizu M., Iwasaki Y., Shibamoto Y., Sato M., DeLuca H.F., and Yamada S. Bioorg. Med. Chem. Lett. 13 (2003) 809
11. Shimizu M., Yamamoto K., Mihori M., Iwasaki Y., Morizono D., and Yamada S. J. Steroid Biochem. Mol. Biol. 89-90 (2004) 75
12. Shimizu M., Iwasaki Y., Shimazaki M., Amano Y., Yamamoto K., Reischl W., and Yamada S. Bioorg. Med. Chem. Lett. 15 (2005) 1451
13. Shimizu M., Miyamoto Y., Kobayashi E., Shimazaki M., Yamamoto K., Wolfgang R., and Yamada S. Bioorg. Med. Chem. 14 (2006) 4277
14. Shimazaki M., Miyamoto Y., Yamamoto K., Yamada S., Takami M., Shinki T., Udagawa N., and Shimizu M. Bioorg. Med. Chem. 14 (2006) 4645
15. Kobayashi E., Shimazaki M., Miyamoto Y., Masuno H., Yamamoto K., DeLuca H.F., Yamada S., and Shimizu M. Bioorg. Med. Chem. 15 (2007) 1475
16. Sato M., Nakamichi Y., Nakamura M., Sato N., Ninomiya T., Muto A., Nakamura H., Iwasaki Y., Kobayashi E., Shimizu M., DeLuca H.F., Takahashi N., and Udagawa N. Bone 40 (2007) 293
17. Honda A., Mori Y., Otomo S., Ishizuka S., and Ikekawa N. Steroid 56 (1991) 142
18. Strugnell S.A., Hill J.J., McCaslin D.R., Wiefling B.A., Royer C.A., and DeLuca H.F. Arch. Biochem. Biophys. 364 (1999) 42
19. Rochel N., Wurtz J.M., Mitschler A., Klaholz B., and Moras D. Mol. Cell 5 (2000) 173
20. Tocchini-Valentini G., Rochel N., Wurtz J.M., Mitschler A., and Moras D. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 5491
21. Tocchini-Valentini G., Rochel N., Wurtz J.M., and Moras D. J. Med. Chem. 47 (2004) 1956
22. Eelen G., Verlinden L., Rochel N., Claessens F., De Clercq P., Vandewalle M., Tocchini-Valentini G., Moras D., Bouillon R., and Verstuyf A. Mol. Pharmacol. 67 (2005) 1566
23. Hourai S., Fujishima T., Kittaka A., Suhara Y., Takayama H., Rochel N., and Moras D. J. Med. Chem. 49 (2006) 5199
24. Ciesielski F., Rochel N., and Moras D. J. Steroid Biochem. Mol. Biol. 103 (2007) 235
25. Vanhooke J.L., Tade B.P., Benning M.M., Plum L.A., and DeLuca H.F. Arch. Biochem. Biophys. 460 (2007) 161
26. ochel N., Hourai S., Pérez-Garcia X., Rumbo A., Mourino A., and Moras D. Arch. Biochem. Biophys. 460 (2007) 172
27. Peleg S., Sastry M., Collins E.D., Bishop J.E., and Norman A.W. J. Biol. Chem. 270 (1995) 10551
28. Hansen C.M., Hamberg K.J., Binderup E., and Binderup L. Curr. Pharm. Des. 6 (2000) 803
29. Choi M., Yamamoto K., Masuno H., Nakashima K., Taga T., and Yamada S. Bioorg. Med. Chem. 9 (2001) 1721
30. Koga T., Nishihara T., Fujiwara T., Nishizawa T., Okahashi N., Noguchi T., and Hamada S. Infect. Immun. 47 (1985) 638
31. Suda T., Jimi E., Nakamura I., and Takahashi N. Methods Enzymol. 282 (1997) 223
32. Li X., Udagawa N., Itoh K., Suda K., Murase Y., Nishihara T., Suda T., and Takahashi N. Endocrinology 143 (2002) 3105