Design and synthesis of potent vitamin D receptor antagonists with A-ring modifications: Remarkable effects of 2α-methyl introduction on antagonistic activity

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 17, 2003, Pages 3621-3631

  Fujishima, Toshie ^a   Kojima, Yoshinori ^a   Azumaya, Isao ^b   Kittaka, Atsushi ^a   Takayama, Hiroaki ^a  

^a TEIKYO UNIVERSITY   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,24 TRIHYDROXY 26,27 CYCLO 9,10 SECOCHOLESTA 5,7,10(19),22 TETRAENE 25 CARBOXYLIC ACID BUTYL ESTER; 20 EPICALCITRIOL; 22 OXACALCITRIOL; 2ALPHA METHYL 1ALPHA,25 DIHYDROVITAMIN D3; BUTYL 26,27 CYCLO 1,3,24 TRIHYDROXY 2 METHYL 9,10 SECO 5,7,10(19),22 CHOLESTATETRAENE 25 CARBOXYLATE; BUTYL 26,27 CYCLO 1,3,24 TRIHYDROXY 9,10 SECO 5,7,10(19),22 CHOLESTATETRAENE 25 CARBOXYLATE; CALCIPOTRIOL; RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG; VITAMIN D RECEPTOR ANTAGONIST;

ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CELL DIFFERENTIATION; CELL STRAIN HL 60; CHEMICAL MODIFICATION; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; HYBRIDIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RECEPTOR AFFINITY; X RAY ANALYSIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0042122298     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00371-7     Document Type: Article

References (64)

1. (a) Vitamin D Physiology, Molecular Biology, and Clinical Applications. Holick M. F., Ed.; Humana Press: Totowa, 1999. (b) Ettinger R.A., DeLuca H.F. Adv. Drug. Res. 28:1996;269 (c) Bouillon R., Okamura W.H., Norman A.W. Endocr. Rev. 16:1995;200.
2. (a) Vitamin D Physiology, Molecular Biology, and Clinical Applications. Holick M. F., Ed.; Humana Press: Totowa, 1999. (b) Ettinger R.A., DeLuca H.F. Adv. Drug. Res. 28:1996;269 (c) Bouillon R., Okamura W.H., Norman A.W. Endocr. Rev. 16:1995;200.
3. (a) Vitamin D Physiology, Molecular Biology, and Clinical Applications. Holick M. F., Ed.; Humana Press: Totowa, 1999. (b) Ettinger R.A., DeLuca H.F. Adv. Drug. Res. 28:1996;269 (c) Bouillon R., Okamura W.H., Norman A.W. Endocr. Rev. 16:1995;200.
4. Evans R.M. Science. 240:1988;889.
5. (a) Rochel N., Wurtz J.M., Mitschler A., Klaholz B., Moras D. Mol. Cell. 5:2000;173 (b) Tocchini-Valentini G., Rochel N., Wurtz J.M., Mitschler A., Moras D. Proc. Natl. Acad. Sci. U.S.A. 98:2001;5491.
6. (a) Rochel N., Wurtz J.M., Mitschler A., Klaholz B., Moras D. Mol. Cell. 5:2000;173 (b) Tocchini-Valentini G., Rochel N., Wurtz J.M., Mitschler A., Moras D. Proc. Natl. Acad. Sci. U.S.A. 98:2001;5491.
7. (a) Takeyama K., Masuhiro Y., Fuse H., Endoh H., Murayama A., Kitanaka S., Suzawa M., Yanagisawa J., Kato S. Mol. Cell. Biol. 19:1999;1049 (b) Kodera Y., Takeyama K., Murayama A., Suzawa M., Masuhiro Y., Kato S. J. Biol. Chem. 275:2000;33201 (c) Fujishima T., Kittaka A., Yamaoka K., Takeyama K., Kato S., Takayama H. Org. Biomol. Chem. 1:2003;1863.
8. (a) Takeyama K., Masuhiro Y., Fuse H., Endoh H., Murayama A., Kitanaka S., Suzawa M., Yanagisawa J., Kato S. Mol. Cell. Biol. 19:1999;1049 (b) Kodera Y., Takeyama K., Murayama A., Suzawa M., Masuhiro Y., Kato S. J. Biol. Chem. 275:2000;33201 (c) Fujishima T., Kittaka A., Yamaoka K., Takeyama K., Kato S., Takayama H. Org. Biomol. Chem. 1:2003;1863.
9. (a) Takeyama K., Masuhiro Y., Fuse H., Endoh H., Murayama A., Kitanaka S., Suzawa M., Yanagisawa J., Kato S. Mol. Cell. Biol. 19:1999;1049 (b) Kodera Y., Takeyama K., Murayama A., Suzawa M., Masuhiro Y., Kato S. J. Biol. Chem. 275:2000;33201 (c) Fujishima T., Kittaka A., Yamaoka K., Takeyama K., Kato S., Takayama H. Org. Biomol. Chem. 1:2003;1863.
10. (a) Carlberg C. J. Cell. Biochem. 88:2003;274 (b) Väisänen S., Peräkylä M., Kärkkäinen J., Steinmeyer A., Carlberg C. J. Mol. Biol. 315:2002;229 (c) Xu H.E., Stanley T.B., Montana V.G., Lambert M.H., Shearer B.G., Cobb J.E., McKee D.D., Galardi C.M., Plunket K.D., Nolte R.T., Parks D.J., Moore J.T., Kiliewer S.A., Willson T.M., Stimmel J.B. Nature. 415:2002;813 (d) Schapira M., Raaka B.M., Samuels H.H., Abagyan R. Proc. Natl. Acad. Sci. U.S.A. 97:2000;1008.
11. (a) Carlberg C. J. Cell. Biochem. 88:2003;274 (b) Väisänen S., Peräkylä M., Kärkkäinen J., Steinmeyer A., Carlberg C. J. Mol. Biol. 315:2002;229 (c) Xu H.E., Stanley T.B., Montana V.G., Lambert M.H., Shearer B.G., Cobb J.E., McKee D.D., Galardi C.M., Plunket K.D., Nolte R.T., Parks D.J., Moore J.T., Kiliewer S.A., Willson T.M., Stimmel J.B. Nature. 415:2002;813 (d) Schapira M., Raaka B.M., Samuels H.H., Abagyan R. Proc. Natl. Acad. Sci. U.S.A. 97:2000;1008.
12. (a) Carlberg C. J. Cell. Biochem. 88:2003;274 (b) Väisänen S., Peräkylä M., Kärkkäinen J., Steinmeyer A., Carlberg C. J. Mol. Biol. 315:2002;229 (c) Xu H.E., Stanley T.B., Montana V.G., Lambert M.H., Shearer B.G., Cobb J.E., McKee D.D., Galardi C.M., Plunket K.D., Nolte R.T., Parks D.J., Moore J.T., Kiliewer S.A., Willson T.M., Stimmel J.B. Nature. 415:2002;813 (d) Schapira M., Raaka B.M., Samuels H.H., Abagyan R. Proc. Natl. Acad. Sci. U.S.A. 97:2000;1008.
13. (a) Carlberg C. J. Cell. Biochem. 88:2003;274 (b) Väisänen S., Peräkylä M., Kärkkäinen J., Steinmeyer A., Carlberg C. J. Mol. Biol. 315:2002;229 (c) Xu H.E., Stanley T.B., Montana V.G., Lambert M.H., Shearer B.G., Cobb J.E., McKee D.D., Galardi C.M., Plunket K.D., Nolte R.T., Parks D.J., Moore J.T., Kiliewer S.A., Willson T.M., Stimmel J.B. Nature. 415:2002;813 (d) Schapira M., Raaka B.M., Samuels H.H., Abagyan R. Proc. Natl. Acad. Sci. U.S.A. 97:2000;1008.
14. (a) Murayama E., Miyamoto K., Kubodera N., Mori T., Matsunaga I. Chem. Pharm. Bull. 34:1986;4410 (b) Abe J., Nakano T., Nishii Y., Matsumoto T., Ogata E., Ikeda K. Endocrinology. 129:1991;832.
15. (a) Murayama E., Miyamoto K., Kubodera N., Mori T., Matsunaga I. Chem. Pharm. Bull. 34:1986;4410 (b) Abe J., Nakano T., Nishii Y., Matsumoto T., Ogata E., Ikeda K. Endocrinology. 129:1991;832.
16. Calverley M.J. Tetrahedron. 43:1987;4609.
17. (a) Binderup L., Latini S., Binderup E., Bretting C., Calverley M.J., Hansen K. Biochem. Pharmacol. 42:1991;1569 (b) Dilworth F.J., Calverley M.J., Makin H.L., Jones G. ibid. 47:1994;987.
18. (a) Binderup L., Latini S., Binderup E., Bretting C., Calverley M.J., Hansen K. Biochem. Pharmacol. 42:1991;1569 (b) Dilworth F.J., Calverley M.J., Makin H.L., Jones G. ibid. 47:1994;987.
19. (a) Norman A.W., Bouillon R., Farach-Carson M.C., Bishop J.E., Zhou L.-X., Nemere L., Zhao J., Muralidoharan K.R., Okamura W.H. J. Biol. Chem. 268:1993;20022 (b) Muralidoharan K.R., de Lera A.R., Isaeff S.D., Norman A.W., Okamura W.H. J. Org. Chem. 58:1993;1895 (c) Bischof M.G., Siu-Caldera M.-L., Weiskopf A., Vouros P., Cross H.S., Peterlik M., Reddy G.S. Exp. Cell. Res. 241:1998;194.
20. (a) Norman A.W., Bouillon R., Farach-Carson M.C., Bishop J.E., Zhou L.-X., Nemere L., Zhao J., Muralidoharan K.R., Okamura W.H. J. Biol. Chem. 268:1993;20022 (b) Muralidoharan K.R., de Lera A.R., Isaeff S.D., Norman A.W., Okamura W.H. J. Org. Chem. 58:1993;1895 (c) Bischof M.G., Siu-Caldera M.-L., Weiskopf A., Vouros P., Cross H.S., Peterlik M., Reddy G.S. Exp. Cell. Res. 241:1998;194.
21. (a) Norman A.W., Bouillon R., Farach-Carson M.C., Bishop J.E., Zhou L.-X., Nemere L., Zhao J., Muralidoharan K.R., Okamura W.H. J. Biol. Chem. 268:1993;20022 (b) Muralidoharan K.R., de Lera A.R., Isaeff S.D., Norman A.W., Okamura W.H. J. Org. Chem. 58:1993;1895 (c) Bischof M.G., Siu-Caldera M.-L., Weiskopf A., Vouros P., Cross H.S., Peterlik M., Reddy G.S. Exp. Cell. Res. 241:1998;194.
22. (a) Konno K., Maki S., Fujishima T., Liu Z.-P., Miura D., Chokki M., Takayama H. Bioorg. Med. Chem. Lett. 8:1998;151 (b) Fujishima T., Liu Z.-P., Miura D., Chokki M., Ishizuka S., Konno K., Takayama H. ibid. 8:1998;2145 (c) Konno K., Fujishima T., Maki S., Liu Z.-P., Miura D., Chokki M., Ishizuka S., Yamaguchi K., Kan Y., Kurihara M., Miyata N., Smith C., DeLuca H.F., Takayama H. J. Med. Chem. 43:2000;4247 (d) Fujishima T., Konno K., Nakagawa K., Kurobe M., Okano T., Takayama H. Bioorg. Med. Chem. 8:2000;123 (e) Nakagawa K., Kurobe M., Ozono K., Konno K., Fujishima T., Takayama H., Okano T. Biochem. Pharmacol. 59:2000;691 (f) Nakagawa K., Kurobe M., Konno K., Fujishima T., Takayama H., Okano T. ibid. 60:2000;1937.
23. (a) Konno K., Maki S., Fujishima T., Liu Z.-P., Miura D., Chokki M., Takayama H. Bioorg. Med. Chem. Lett. 8:1998;151 (b) Fujishima T., Liu Z.-P., Miura D., Chokki M., Ishizuka S., Konno K., Takayama H. ibid. 8:1998;2145 (c) Konno K., Fujishima T., Maki S., Liu Z.-P., Miura D., Chokki M., Ishizuka S., Yamaguchi K., Kan Y., Kurihara M., Miyata N., Smith C., DeLuca H.F., Takayama H. J. Med. Chem. 43:2000;4247 (d) Fujishima T., Konno K., Nakagawa K., Kurobe M., Okano T., Takayama H. Bioorg. Med. Chem. 8:2000;123 (e) Nakagawa K., Kurobe M., Ozono K., Konno K., Fujishima T., Takayama H., Okano T. Biochem. Pharmacol. 59:2000;691 (f) Nakagawa K., Kurobe M., Konno K., Fujishima T., Takayama H., Okano T. ibid. 60:2000;1937.
24. (a) Konno K., Maki S., Fujishima T., Liu Z.-P., Miura D., Chokki M., Takayama H. Bioorg. Med. Chem. Lett. 8:1998;151 (b) Fujishima T., Liu Z.-P., Miura D., Chokki M., Ishizuka S., Konno K., Takayama H. ibid. 8:1998;2145 (c) Konno K., Fujishima T., Maki S., Liu Z.-P., Miura D., Chokki M., Ishizuka S., Yamaguchi K., Kan Y., Kurihara M., Miyata N., Smith C., DeLuca H.F., Takayama H. J. Med. Chem. 43:2000;4247 (d) Fujishima T., Konno K., Nakagawa K., Kurobe M., Okano T., Takayama H. Bioorg. Med. Chem. 8:2000;123 (e) Nakagawa K., Kurobe M., Ozono K., Konno K., Fujishima T., Takayama H., Okano T. Biochem. Pharmacol. 59:2000;691 (f) Nakagawa K., Kurobe M., Konno K., Fujishima T., Takayama H., Okano T. ibid. 60:2000;1937.
25. (a) Konno K., Maki S., Fujishima T., Liu Z.-P., Miura D., Chokki M., Takayama H. Bioorg. Med. Chem. Lett. 8:1998;151 (b) Fujishima T., Liu Z.-P., Miura D., Chokki M., Ishizuka S., Konno K., Takayama H. ibid. 8:1998;2145 (c) Konno K., Fujishima T., Maki S., Liu Z.-P., Miura D., Chokki M., Ishizuka S., Yamaguchi K., Kan Y., Kurihara M., Miyata N., Smith C., DeLuca H.F., Takayama H. J. Med. Chem. 43:2000;4247 (d) Fujishima T., Konno K., Nakagawa K., Kurobe M., Okano T., Takayama H. Bioorg. Med. Chem. 8:2000;123 (e) Nakagawa K., Kurobe M., Ozono K., Konno K., Fujishima T., Takayama H., Okano T. Biochem. Pharmacol. 59:2000;691 (f) Nakagawa K., Kurobe M., Konno K., Fujishima T., Takayama H., Okano T. ibid. 60:2000;1937.
26. (a) Konno K., Maki S., Fujishima T., Liu Z.-P., Miura D., Chokki M., Takayama H. Bioorg. Med. Chem. Lett. 8:1998;151 (b) Fujishima T., Liu Z.-P., Miura D., Chokki M., Ishizuka S., Konno K., Takayama H. ibid. 8:1998;2145 (c) Konno K., Fujishima T., Maki S., Liu Z.-P., Miura D., Chokki M., Ishizuka S., Yamaguchi K., Kan Y., Kurihara M., Miyata N., Smith C., DeLuca H.F., Takayama H. J. Med. Chem. 43:2000;4247 (d) Fujishima T., Konno K., Nakagawa K., Kurobe M., Okano T., Takayama H. Bioorg. Med. Chem. 8:2000;123 (e) Nakagawa K., Kurobe M., Ozono K., Konno K., Fujishima T., Takayama H., Okano T. Biochem. Pharmacol. 59:2000;691 (f) Nakagawa K., Kurobe M., Konno K., Fujishima T., Takayama H., Okano T. ibid. 60:2000;1937.
27. (a) Konno K., Maki S., Fujishima T., Liu Z.-P., Miura D., Chokki M., Takayama H. Bioorg. Med. Chem. Lett. 8:1998;151 (b) Fujishima T., Liu Z.-P., Miura D., Chokki M., Ishizuka S., Konno K., Takayama H. ibid. 8:1998;2145 (c) Konno K., Fujishima T., Maki S., Liu Z.-P., Miura D., Chokki M., Ishizuka S., Yamaguchi K., Kan Y., Kurihara M., Miyata N., Smith C., DeLuca H.F., Takayama H. J. Med. Chem. 43:2000;4247 (d) Fujishima T., Konno K., Nakagawa K., Kurobe M., Okano T., Takayama H. Bioorg. Med. Chem. 8:2000;123 (e) Nakagawa K., Kurobe M., Ozono K., Konno K., Fujishima T., Takayama H., Okano T. Biochem. Pharmacol. 59:2000;691 (f) Nakagawa K., Kurobe M., Konno K., Fujishima T., Takayama H., Okano T. ibid. 60:2000;1937.
28. (a) Fujishima T., Liu Z.-P., Konno K., Nakagawa K., Okano T., Yamaguchi K., Takayama H. Bioorg. Med. Chem. 9:2001;525 (b) Fujishima T., Konno K., Nakagawa K., Tanaka M., Okano T., Kurihara M., Miyata N., Takayama H. Chem. Biol. 8:2001;1011 (c) Suhara Y., Kittaka A., Kishimoto S., Calverley M.J., Fujishima T., Saiso N., Sugiura T., Waku K., Takayama H. Bioorg. Med. Chem. Lett. 12:2002;3255.
29. (a) Fujishima T., Liu Z.-P., Konno K., Nakagawa K., Okano T., Yamaguchi K., Takayama H. Bioorg. Med. Chem. 9:2001;525 (b) Fujishima T., Konno K., Nakagawa K., Tanaka M., Okano T., Kurihara M., Miyata N., Takayama H. Chem. Biol. 8:2001;1011 (c) Suhara Y., Kittaka A., Kishimoto S., Calverley M.J., Fujishima T., Saiso N., Sugiura T., Waku K., Takayama H. Bioorg. Med. Chem. Lett. 12:2002;3255.
30. (a) Fujishima T., Liu Z.-P., Konno K., Nakagawa K., Okano T., Yamaguchi K., Takayama H. Bioorg. Med. Chem. 9:2001;525 (b) Fujishima T., Konno K., Nakagawa K., Tanaka M., Okano T., Kurihara M., Miyata N., Takayama H. Chem. Biol. 8:2001;1011 (c) Suhara Y., Kittaka A., Kishimoto S., Calverley M.J., Fujishima T., Saiso N., Sugiura T., Waku K., Takayama H. Bioorg. Med. Chem. Lett. 12:2002;3255.
31. (a) Herdick M., Steinmeyer A., Carlberg C. J. Biol. Chem. 275:2000;16506 (b) Herdick M., Steinmeyer A., Carlberg C. Chem. Biol. 7:2000;885 (c) Bury Y., Steinmeyer A., Carlberg C. Mol. Pharmacol. 58:2000;1067 (d) Toell A., Gonzalez M.M., Ruf D., Steinmeyer A., Ishizuka S., Carlberg C. ibid. 59:2001;1478.
32. (a) Herdick M., Steinmeyer A., Carlberg C. J. Biol. Chem. 275:2000;16506 (b) Herdick M., Steinmeyer A., Carlberg C. Chem. Biol. 7:2000;885 (c) Bury Y., Steinmeyer A., Carlberg C. Mol. Pharmacol. 58:2000;1067 (d) Toell A., Gonzalez M.M., Ruf D., Steinmeyer A., Ishizuka S., Carlberg C. ibid. 59:2001;1478.
33. (a) Herdick M., Steinmeyer A., Carlberg C. J. Biol. Chem. 275:2000;16506 (b) Herdick M., Steinmeyer A., Carlberg C. Chem. Biol. 7:2000;885 (c) Bury Y., Steinmeyer A., Carlberg C. Mol. Pharmacol. 58:2000;1067 (d) Toell A., Gonzalez M.M., Ruf D., Steinmeyer A., Ishizuka S., Carlberg C. ibid. 59:2001;1478.
34. (a) Herdick M., Steinmeyer A., Carlberg C. J. Biol. Chem. 275:2000;16506 (b) Herdick M., Steinmeyer A., Carlberg C. Chem. Biol. 7:2000;885 (c) Bury Y., Steinmeyer A., Carlberg C. Mol. Pharmacol. 58:2000;1067 (d) Toell A., Gonzalez M.M., Ruf D., Steinmeyer A., Ishizuka S., Carlberg C. ibid. 59:2001;1478.
35. (a) Miura D., Manabe K., Ozono K., Saito M., Gao Q., Norman A.W., Ishizuka S. J. Biol. Chem. 274:1999;16392 (b) Miura D., Manabe K., Ozono K., Saito M., Gao Q., Norman A.W., Ishizuka S. ibid. 274:1999;33376.
36. (a) Miura D., Manabe K., Ozono K., Saito M., Gao Q., Norman A.W., Ishizuka S. J. Biol. Chem. 274:1999;16392 (b) Miura D., Manabe K., Ozono K., Saito M., Gao Q., Norman A.W., Ishizuka S. ibid. 274:1999;33376.
37. (a) Menaa C., Barsony J., Reddy S.V., Cornish J., Cundy T., Roodman G.D. J. Bone Miner. Res. 15:2000;228 (b) Kurihara N., Reddy S.V., Menaa C., Anderson D., Roodman G.D. J. Clin. Invest. 105:2000;607 (c) Menaa C., Reddy S.V., Kurihara N., Maeda H., Anderson D., Cundy T., Cornish J., Singer F.R., Bruder J.M., Roodman G.D. ibid. 105:2000;1833 (d) Leach R.J., Roodman G.D. J. Clin. Endocrinol. Metab. 86:2001;24 (e) Reddy S.V., Kurihara N., Menaa C., Landucci G., Forthal D., Koop B.A., Windle J.J., Roodman G.D. Endocrinology. 142:2001;2898 (f) Friedrichs W.E., Reddy S.V., Bruder J.M., Cundy T., Cornish J., Singer F.R., Roodman G.D. J. Bone Miner. Res. 17:2002;145.
38. (a) Menaa C., Barsony J., Reddy S.V., Cornish J., Cundy T., Roodman G.D. J. Bone Miner. Res. 15:2000;228 (b) Kurihara N., Reddy S.V., Menaa C., Anderson D., Roodman G.D. J. Clin. Invest. 105:2000;607 (c) Menaa C., Reddy S.V., Kurihara N., Maeda H., Anderson D., Cundy T., Cornish J., Singer F.R., Bruder J.M., Roodman G.D. ibid. 105:2000;1833 (d) Leach R.J., Roodman G.D. J. Clin. Endocrinol. Metab. 86:2001;24 (e) Reddy S.V., Kurihara N., Menaa C., Landucci G., Forthal D., Koop B.A., Windle J.J., Roodman G.D. Endocrinology. 142:2001;2898 (f) Friedrichs W.E., Reddy S.V., Bruder J.M., Cundy T., Cornish J., Singer F.R., Roodman G.D. J. Bone Miner. Res. 17:2002;145.
39. (a) Menaa C., Barsony J., Reddy S.V., Cornish J., Cundy T., Roodman G.D. J. Bone Miner. Res. 15:2000;228 (b) Kurihara N., Reddy S.V., Menaa C., Anderson D., Roodman G.D. J. Clin. Invest. 105:2000;607 (c) Menaa C., Reddy S.V., Kurihara N., Maeda H., Anderson D., Cundy T., Cornish J., Singer F.R., Bruder J.M., Roodman G.D. ibid. 105:2000;1833 (d) Leach R.J., Roodman G.D. J. Clin. Endocrinol. Metab. 86:2001;24 (e) Reddy S.V., Kurihara N., Menaa C., Landucci G., Forthal D., Koop B.A., Windle J.J., Roodman G.D. Endocrinology. 142:2001;2898 (f) Friedrichs W.E., Reddy S.V., Bruder J.M., Cundy T., Cornish J., Singer F.R., Roodman G.D. J. Bone Miner. Res. 17:2002;145.
40. (a) Menaa C., Barsony J., Reddy S.V., Cornish J., Cundy T., Roodman G.D. J. Bone Miner. Res. 15:2000;228 (b) Kurihara N., Reddy S.V., Menaa C., Anderson D., Roodman G.D. J. Clin. Invest. 105:2000;607 (c) Menaa C., Reddy S.V., Kurihara N., Maeda H., Anderson D., Cundy T., Cornish J., Singer F.R., Bruder J.M., Roodman G.D. ibid. 105:2000;1833 (d) Leach R.J., Roodman G.D. J. Clin. Endocrinol. Metab. 86:2001;24 (e) Reddy S.V., Kurihara N., Menaa C., Landucci G., Forthal D., Koop B.A., Windle J.J., Roodman G.D. Endocrinology. 142:2001;2898 (f) Friedrichs W.E., Reddy S.V., Bruder J.M., Cundy T., Cornish J., Singer F.R., Roodman G.D. J. Bone Miner. Res. 17:2002;145.
41. (a) Menaa C., Barsony J., Reddy S.V., Cornish J., Cundy T., Roodman G.D. J. Bone Miner. Res. 15:2000;228 (b) Kurihara N., Reddy S.V., Menaa C., Anderson D., Roodman G.D. J. Clin. Invest. 105:2000;607 (c) Menaa C., Reddy S.V., Kurihara N., Maeda H., Anderson D., Cundy T., Cornish J., Singer F.R., Bruder J.M., Roodman G.D. ibid. 105:2000;1833 (d) Leach R.J., Roodman G.D. J. Clin. Endocrinol. Metab. 86:2001;24 (e) Reddy S.V., Kurihara N., Menaa C., Landucci G., Forthal D., Koop B.A., Windle J.J., Roodman G.D. Endocrinology. 142:2001;2898 (f) Friedrichs W.E., Reddy S.V., Bruder J.M., Cundy T., Cornish J., Singer F.R., Roodman G.D. J. Bone Miner. Res. 17:2002;145.
42. (a) Menaa C., Barsony J., Reddy S.V., Cornish J., Cundy T., Roodman G.D. J. Bone Miner. Res. 15:2000;228 (b) Kurihara N., Reddy S.V., Menaa C., Anderson D., Roodman G.D. J. Clin. Invest. 105:2000;607 (c) Menaa C., Reddy S.V., Kurihara N., Maeda H., Anderson D., Cundy T., Cornish J., Singer F.R., Bruder J.M., Roodman G.D. ibid. 105:2000;1833 (d) Leach R.J., Roodman G.D. J. Clin. Endocrinol. Metab. 86:2001;24 (e) Reddy S.V., Kurihara N., Menaa C., Landucci G., Forthal D., Koop B.A., Windle J.J., Roodman G.D. Endocrinology. 142:2001;2898 (f) Friedrichs W.E., Reddy S.V., Bruder J.M., Cundy T., Cornish J., Singer F.R., Roodman G.D. J. Bone Miner. Res. 17:2002;145.
43. (a) Higashi T., Kikuchi R., Miura K., Shimada K., Hiyamizu H., Ooi H., Iwabuchi Y., Hatakeyama S., Kubodera N. Biol. Pharm. Bull. 22:1999;767 (b) Siu-Caldera M., Sunita Rao D., Astecker N., Weiskopf A., Vouros P., Konno K., Fujishima T., Takayama H., Peleg S., Reddy G.S. J. Cell. Biochem. 82:2001;599 (c) Sunita Rao D., Siu-Caldera M.-L., Sekimoto H., Gennaro L., Vouros P., Takayama H., Konno K., Fujishima T., Reddy G.S. Biol. Pharm. Bull. 25:2002;845.
44. (a) Higashi T., Kikuchi R., Miura K., Shimada K., Hiyamizu H., Ooi H., Iwabuchi Y., Hatakeyama S., Kubodera N. Biol. Pharm. Bull. 22:1999;767 (b) Siu-Caldera M., Sunita Rao D., Astecker N., Weiskopf A., Vouros P., Konno K., Fujishima T., Takayama H., Peleg S., Reddy G.S. J. Cell. Biochem. 82:2001;599 (c) Sunita Rao D., Siu-Caldera M.-L., Sekimoto H., Gennaro L., Vouros P., Takayama H., Konno K., Fujishima T., Reddy G.S. Biol. Pharm. Bull. 25:2002;845.
45. (a) Higashi T., Kikuchi R., Miura K., Shimada K., Hiyamizu H., Ooi H., Iwabuchi Y., Hatakeyama S., Kubodera N. Biol. Pharm. Bull. 22:1999;767 (b) Siu-Caldera M., Sunita Rao D., Astecker N., Weiskopf A., Vouros P., Konno K., Fujishima T., Takayama H., Peleg S., Reddy G.S. J. Cell. Biochem. 82:2001;599 (c) Sunita Rao D., Siu-Caldera M.-L., Sekimoto H., Gennaro L., Vouros P., Takayama H., Konno K., Fujishima T., Reddy G.S. Biol. Pharm. Bull. 25:2002;845.
46. For reviews of synthesis of vitamin D compounds, see:(a) Zhu G.-D., Okamura W.H. Chem. Rev. 95:1995;1877 (b) Dai H., Posner G.H. Synthesis. 1994;1383.
47. For reviews of synthesis of vitamin D compounds, see:(a) Zhu G.-D., Okamura W.H. Chem. Rev. 95:1995;1877 (b) Dai H., Posner G.H. Synthesis. 1994;1383.
48. (a) Trost B.M., Dumas J., Villa M. J. Am. Chem. Soc. 114:1992;9836 (b) Trost B.M., Dumas J. ibid. 114:1992;1924.
49. (a) Trost B.M., Dumas J., Villa M. J. Am. Chem. Soc. 114:1992;9836 (b) Trost B.M., Dumas J. ibid. 114:1992;1924.
50. (a) Okamoto M., Fujii T., Tanaka T. Tetrahedron. 51:1995;5543 (b) Daniel D., Middleton R., Henry H.L., Okamura W.H. J. Org. Chem. 61:1996;5617 (c) Ikeda M., Takahashi K., Dan A., Koyama K., Kubota K., Tanaka T., Hayashi M. Bioorg. Med. Chem. 8:2000;2157.
51. (a) Okamoto M., Fujii T., Tanaka T. Tetrahedron. 51:1995;5543 (b) Daniel D., Middleton R., Henry H.L., Okamura W.H. J. Org. Chem. 61:1996;5617 (c) Ikeda M., Takahashi K., Dan A., Koyama K., Kubota K., Tanaka T., Hayashi M. Bioorg. Med. Chem. 8:2000;2157.
52. (a) Okamoto M., Fujii T., Tanaka T. Tetrahedron. 51:1995;5543 (b) Daniel D., Middleton R., Henry H.L., Okamura W.H. J. Org. Chem. 61:1996;5617 (c) Ikeda M., Takahashi K., Dan A., Koyama K., Kubota K., Tanaka T., Hayashi M. Bioorg. Med. Chem. 8:2000;2157.
53. The A-ring enyne synthons, 15a and 15b, correspond to (3S,4S,5R)- and (3S,4S,5S)-bis[(tert-butyldimethylsilyl)oxy]-4-methyloct-1-en-7-yne: See refs 10a-c.
54. Fernández B., Pérez J.A.M., Granja J.R., Castedo L., Mourinõ A. J. Org. Chem. 57:1992;3173.
55. Taber D.F., Hennessy M.J., Louey J.P. J. Org. Chem. 57:1992;436.
56. Ohtani I., Kusumi T., Kashman Y., Kakisawa H. J. Am. Chem. Soc. 113:1991;4092.
57. Harada N., Iwabuchi J., Yokota Y., Uda H., Nakanishi K. J. Am. Chem. Soc. 103:1981;5590.
58. The exciton theory predicts that, if the two long axes of benzoate and double-bond chromophores constitute a positive exciton chirality, i.e., right-handed screwness, the Cotton effect at 230 nm is positive. On the other hand, if the allylic benzoate constitutes a negative exciton chirality, the Cotton effect should be negative: see ref 23.
59. The side-chain conformations of 18a,b were calculated using model compounds having a 9-(trimethylsilyl)oxy group, instead of the 9-(tert-butyldimethylsilyl)oxy group, and methyl ester at the C25 position, instead of butyl ester. The Monte Carlo conformational searches based on the MMFF 94 force field were performed using Spartan '02 for Linux, Wavefunction, Inc.
60. Ogawa S., Shibasaki M. Tetrahedron Lett. 25:1984;663.
61. Imae Y., Manaka A., Yoshida N., Ishimi Y., Shinki T., Abe E., Suda T., Konno K., Takayama H., Yamada S. Biochim. Biophys. Acta. 1213:1994;302.
62. Wurtz, J.-M.; Guillot, B.; Moras, D. In Vitamin D: Chemistry, Biology and Clinical Applications of the Steroid Hormone: Proceedings of the 10th Workshop on Vitamin D. Norman, A. W., Bouillon, R., Thomasset, M. Eds.; University of California, Printing and Reprographics: Riverside, 1997; p 165.
63. Abe E., Miyaura C., Sakagami C., Takeda H., Konno K., Yamazaki K., Yashiki T., Suda T. Proc. Natl. Acad. Sci. U.S.A. 78:1981;4990.
64. Collins S.J., Ruscetti F.W., Gallagher R.E., Gallo R.C. J. Exp. Med. 149:1979;969.