Recent results on A-ring modification of 1α,25-dihydroxyvitamin D3: Design and synthesis of VDR-agonists and antagonists with high biological activity

Current Topics in Medicinal Chemistry

Volumn 6, Issue 12, 2006, Pages 1273-1288

  Saito, Nozomi ^a   Honzawa, Shinobu ^a   Kittaka, Atsushi ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

B seco steroidal; CD ring lactones; Docking; HL 60 Cell Differentiation; Palladium coupling

Indexed keywords

1,3,24 TRIHYDROXY 26,27 CYCLO 9,10 SECOCHOLESTA 5,7,10(19),22 TETRAENE 25 CARBOXYLIC ACID BUTYL ESTER; 2 METHYLENE 19 NORCALCITRIOL; 20 EPICALCITRIOL; 2ALPHA (OMEGA HYDROXYALKYL) 20 EPICALCITRIOL DERIVATIVE; 2ALPHA (OMEGA HYDROXYPROPOXY)CALCITRIOL; 2BETA (3 HYDROXYPROPOXY)CALCITRIOL; CALCITRIOL DERIVATIVE; COLECALCIFEROL DERIVATIVE; GLUCOSE; QUINIC ACID; TEI 9647; TEI 9648; UNCLASSIFIED DRUG; VITAMIN D RECEPTOR AGONIST; VITAMIN D RECEPTOR ANTAGONIST; ZK 168281;

BONE DISEASE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; DRUG DESIGN; DRUG INDICATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; OLEFINATION; PSORIASIS; REVIEW; SECONDARY HYPERPARATHYROIDISM; STRUCTURE ANALYSIS;

CALCITRIOL; MOLECULAR STRUCTURE; RECEPTORS, CALCITRIOL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33746326524     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802606777864953     Document Type: Review

References (119)

1. Vitamin D; Feldman, D.; Pike, J. W.; Glorieux, F. H.; Eds.; Elsevier Academic Press: New York, 2005.
2. Bouillon, R.; Okamura, W. H.; Norman, A. W. Structure-Function Relationships in the Vitamin D Endocrine System. Endocr. Rev. 1995, 16, 200-257.
3. Ettinger, R. A.; DeLuca, H. F. The Vitamin D Endocrine System and Its Therapeutic Potential. Adv. Drug Res. 1996, 28, 269-312.
4. Evans, R. M. The Steroid and Thyroid Hormone Receptor Superfamily. Science 1988, 240, 889-895.
5. 2Na
6. Yanagisawa, J.; Yanagi, Y.; Masuhiro, Y.; Suzawa, M.; Watanabe, M.; Kashiwagi, K.; Toriyabe, T.; Kawabata, M.; Miyazono, K.; Kato, S. Convergence of Transforming Growth Factor-β and Vitamin D Signaling Pathways on SMAD Transcriptional Coactivators. Science 1999, 283, 1317-1321.
7. Rochel, N.; Wurtz, J. M.; Mitschler, A.; Klaholz, B.; Moras, D. The Crystal Structure of the Nuclear Receptor for Vitamin D Bound to Its Natural Ligand. Mol. Cell 2000, 5, 173-179.
8. For PPAR-γ, see: Nolte, R. T.; Wisely, G. B.; Westin, S.; Cobb, J. E.; Lambert, M. H.; Kurokawa, R.; Rosenfeld, M. G.; Willson, T. M.; Glass, C. K.; Milburn, M. V. Ligand Binding and Co-activator Assembly of the Peroxisome Proliferator-activated Receptor-γ Nature 1998, 395, 137-143.
9. For ER, see: Shiau, A. K.; Barstad, D.; Loria, P. M.; Cheng, L.; Kushner, P. J.; Agard, D. A.; Greene, G. L. The Structural Basis of Estrogen Receptor/Coactivator Recognition and the Antagonism of This Interaction by Tamoxifen. Cell 1998, 95, 927-937.
10. 3. Science 1974, 186, 939-941.
11. 3 by High-resolution Proton Magnetic Resonance Spectroscopy. J. Am. Chem. Soc. 1975, 97, 4980-4985.
12. Okamura, W. H.; Norman, A. W.; Wing, R. M. Vitamin D: Concerning the Relationship between Molecular Topology and Biological Function. Proc. Natl. Acad. Sci. USA 1974, 71, 4194-4197.
13. 13C NMR Analysis of the Conformational. Equilibrium of the A-Ring. Bioorg. Chem. 1991, 19, 327-332.
14. 3 by Nuclear Magnetic Resonance. Bioorg. Chem. 1990, 18, 19-29.
15. 3. J. Org. Chem. 1995, 60, 1828-1833.
16. 3. Bioorg. Med. Chem. Lett. 1998, 8, 151-156.
17. 3 and Their 20-Epimers: Unique Activity Profiles Depending on the Stereochemistry of the A-Ring and at C-20. J. Med. Chem. 2000, 43, 4247-4265.
18. 3: Transactivation of Target Genes and Modulation of Differentiation in Human Promyelocytic Leukemia (HL-60) Cells. Biochem. Pharmacol. 2000, 59, 691-702.
19. 3 Analogues. Bioorg. Med. Chem. Lett. 2000, 10, 1129-1132.
20. 3 Analogues and Their Docking to Vitamin D Receptors. J. Org. Chem. 2001, 66, 8760-8771.
21. 3 Analogues with a Double Side Chain: Marked Cell Differentiation Activity. Bioorg. Med. Chem. Lett. 2002, 12, 3255-3258.
22. 3. Bioorg. Med. Chem. Lett. 2003, 13, 3503-3506.
23. 3 Analogs. In Vitamin D Analogs in Cancer Prevention and Therapy, Recent Results in Cancer Research 164; Reichrath, J., Friedrich, M., Tilgen, W.; Eds.; Springer-Verlag: Berlin Heidelberg, 2003; pp. 289-317.
24. 3 Analogues Bearing a Hydroxyalkoxy Group at the 2β-Position. Chem. Pharm. Bull. 1993, 41, 1111-1113.
25. 3. Biol. Pharm. Bull. 2000, 23, 66-71.
26. 3 Analogs Substituted at the 2β-Position and Their Preventive Effects on Bone Mineral Loss in Ovariectomized Rats. Chem. Pharm. Bull. 1997, 45, 1626-1630.
27. 3 Analogues. Bioorg. Med. Chem. Lett. 1994, 4, 1523-1526.
28. Kubodera, N. Development of OCT and ED-71. In Vitamin D; Feldman, D.; Pike, J. W.; Glorieux, F. H.; Eds.; Elsevier Academic Press: New York, 2005, Chapter 86, pp. 1525-1541.
29. 3 complex, see: Verboven, C.; Rabijns, A.; De Maeyer, M.; Van Baelen, H.; Bouillon, R.; De Ranter C. A Structural Basis for the Unique Binding Features of the Human Vitamin D-Binding Protein. Nature Struct. Biol. 2002, 9, 131-136.
30. 3: Remarkably High Affinity to Vitamin D Receptor. Org. Lett. 2000, 2, 2619-2622.
31. 3 Analogues, Including 2-epi-ED-71 and Their 20-Epimers with HL-60 Cell Differentiation Activity. J. Org. Chem. 2004, 69, 7463-7471.
32. 3 Accessible to Vitamin D Receptor Mutant Related to Hereditary Vitamin D-Resistant Rickets. Chem. Pharm. Bull. 2003, 51, 357-358.
33. 3 Analogs of an Osteoporosis Drug. J. Org. Chem. 1994, 59, 7855-7861.
34. 3. Stereocontrolled Total Synthesis via Intramolecular and Intermolecular Diels-Alder Cycloadditions. Preliminary Biological Testing. J. Org. Chem. 1995, 60, 4617-4628.
35. 3. Bioorg. Med Chem. Lett. 1998, 8, 2145-2148.
36. 3 Analogues: A Novel Class of Potent Regulators of Cell Growth and Immune Responses. Biochem. Pharm 1991, 42, 1569-1575.
37. 3 is due to Reduced Catabolism and Altered Protein Binding. Biochem. Pharm. 1994, 47, 987-993.
38. 3 and Its 20-Epimer. Bioorg. Med. Chem. 2000, 8, 123-134.
39. Trost, B. M.; Dumas, J.; Villa, M. New Strategies for the Synthesis of Vitamin D Metabolites via Pd-Catalyzed Reactions. J. Am. Chem. Soc. 1992, 114, 9836-9845.
40. Wiggins, L. F. Ethylene Oxide-Type Anhydrosugars. Methods Carbohydr. Chem. 1963, 2, 188-191.
41. Beau, J.-M.; Aburaki, S.; Pougny, J-R.; Sinäy, P. Total Synthesis of (+)-Methyl Pseudomonate C from Carbohydrates. J. Am. Chem. Soc. 1983, 105, 621-622.
42. Hanessian, S. Methyl 4-O-Benzoyl-6-bromo-6-deoxyhexopyranosides. Methods Carbohydr. Chem. 1972, 6, 183-189.
43. Hanessian, S.; Plessas, N. R. The Reaction of O-Benzylidene Sugars with N-Bromosuccinimide. II. Scope and Synthetic Utility in the Methyl 4,6-O-Benzylidenehexopyranoside Series. J. Org. Chem. 1969, 34, 1035-1044.
44. Bemotas, R. C.; Pezzone, M. A.; Ganem, B. Synthesis of (+)-1,5-Dideoxy-1, 5-imino-D-galactitol, a Potent α-D-Garactosidase Inhibitor. Carbohydr. Res. 1987, 167, 305-311.
45. Bernet, B.; Vasella, A. Carbocyclische Verbindungen aus Monosacchariden. I. Umsetzungen in der Glucosereihe. Helv. Chim. Acta 1979, 62, 1990-2016.
46. 3 Analogues Utilizing Grignard Reaction Towards Methyl 2,3-Anhydro-4, 6-O-benzylidene-α-D-manno-pyranoside. Heterocycles 2003, 61, 327-338.
47. 3 using a THF solvent, see ref. 21.
48. Inch, T. D.; Lewis, G. J. The Synthesis of Branched-Chain, Deoxy Sugars by Sugar Epoxide-Grignard Reagent Reactions. Carbohydr. Res. 1970, 15, 1-10.
49. 3 Analogues Possessing Aromatic Ring on 2α-Position. Tetrahedron 2005, 61, 11253-11263.
50. 3 Lactones Using Ruthenium-Catalyzed Intermolecular Enyne Metathesis: Potent Vitamin D Receptor Antagonists. Synthesis 2005 (15), 2533-2543.
51. 3-26,23-lactones and Their 2α-Functionalized Analogues as Highly Potent VDR Antagonists. Tetrahedron 2004, 60, 7951-7961.
52. Imae, Y.; Manaka, A.; Yoshida, N.; Ishimi, Y.; Shinki, T.; Abe, E.; Suda, T.; Konno, K.; Takayama, H.; Yamada, S. Biological Activities of 24-Fluoro-1α,25-Dihydroxyvitamin D-2 and Its 24-Epimer. Biochim. Biophys. Acta 1994, 1213, 302-308.
53. 3 with Side-Chain Modifications. Bioorg. Med. Chem. 2001, 9, 525-535.
54. Collins, S. J.; Ruscetti, F. W.; Gallagher, R. E.; Gallo, R. C. Normal Functional Characteristics of Cultured Human Promyelocytic Leukemia Cells (HL-60) After Induction of Differentiation by Dimethylsulfoxide. J. Exp. Med. 1979, 149, 969-974.
55. 3. Chem. Pharm. Bull. 1991, 39, 3221-3224.
56. Tocchini-Valentini, G.; Rochel, N.; Wurtz, J. M.; Mitschler, A.; Moras, D. Crystal Structures of the Vitamin D Receptor Complexed to Superagonist 20-Epi Ligands. Proc. Natl. Acad. Sci. USA 2001, 98, 5491-5496.
57. 3. J. Med. Chem. 2002, 45, 1825-1834.
58. 3 Analog with Two Side Chains. In Vitamin D: Chemistry, Biology, and Clinical Applications of the Steroid Hormone; Norman, A. W.; Bouillon, R.; Thomasset, M.; Eds.; University of California: Riverside Calif., 1997; pp. 19-21.
59. Kurek-Tyrlik, A.; Makaev, F. Z.; Wicha, J.; Zhabinskii, V.; Calverley, M. J. Pivoting 20-Normal and 20-Epi Calcitriols: Synthesis and Crystal Structure of a "Double Side Chain" Analogue. In Vitamin D: Chemistry, Biology, and Clinical Applications of the Steroid Hormone; Norman, A. W.; Bouillon, R.; Thomasset, M.; Eds.; University of California: Riverside Calif., 1997; pp. 30-31.
60. 3 with Two Side Chains: Interaction with Its Nuclear Receptor and Cellular Actions. J. Med. Chem. 2000, 43, 2719-2730.
61. 3, A Novel Vitamin D-related Compound with Potential Therapeutic Activity. Tetrahedron Lett. 1990, 31, 1823-1824.
62. Perlman, K. L.; Swenson, R. E.; Paaren, H. E.; Schnoes, H. K.; DeLuca, H. F. Novel Synthesis of 19-Norvitamin D Compounds. Tetrahedron Lett. 1991, 32, 7663-7666.
63. 3: Synthesis, Conformational Analysis, Biological Activities, and Docking to the Modeled rVDR Ligand Binding Domain. J. Med. Chem. 2002, 45, 3366-3380.
64. Mikami, K.; Osawa, A.; Isaka, A.; Sawa, E.; Shimizu, M.; Terada, M.; Kubodera, N.; Nakagawa, K.; Tsugawa, N.; Okano, T. "Symmetry" in the Synthesis of the A-Ring of a Vitamin D Hybrid Analogue with Significant Transactivation Activity: A Combinatorial Sequence of Regioselective Propiolate-Ene, Catalytic Enantioselective Epoxidation and Carbonyl-Ene Cyclization Reactions. Tetrahedron Lett. 1998, 39, 3359-3362.
65. 3 A-Ring Analogs in Cancer Cell Differentiation and Apoptosis. Chem. Biol. 2000, 7, 173-184.
66. 3- J. Med. Chem. 1994, 37, 3730-3738.
67. 3 Compounds of High Biological Activity: Synthesis and Biological Evaluation of 2-Hydroxymethyl, 2-Methyl and 2-Methylene Analogues. J. Med. Chem. 1998, 41, 4662-4674.
68. 3. In Vitamin D; Feldman, D.; Pike, J. W.; Glorieux, F. H.; Eds.; Elsevier Academic Press: New York, 2005, Chapter 87, pp. 1543-1555.
69. 3 Selectively Induces Bone Formation. Proc. Natl. Acad. Sci. USA 2002, 99, 13487-13491.
70. 3 with 3'-Alkoxypropylidene Moiety at C-2: Synthesis, Biological Activity and Conformational Analysis. J. Steroid Biochem. Mol. Biol. 2004, 89-90, 25-30.
71. Plum, L. A.; Prahl, J. M.; Ma, X.; Sicinski, R. R.; Gowlugari, S.; Clagett-Dame, M.; DeLuca, H. F. Biologically Active Noncalcemic Analogs of 1α,25-Dihydroxyvitamin D with an Abbreviated Side Chain Containing No Hydroxyl. Proc. Natl. Acad. Sci. USA 2004, 101, 6900-6904.
72. 3: Synthesis, Biological Activities and Docking to the Ligand Binding Domain of the Rat Vitamin D Receptor. J. Steroid Biochem. Mol. Biol. 2004, 89-90, 13-17.
73. 3 Analogues. Synlett 2003, 1175-1179.
74. 3 with Julia Olefination: High Potency in Induction of Differentiation on HL-60 Cells. J. Org. Chem. 2003, 68, 7407-7415.
75. Mikaimi, K.; Koizumi Y.; Osawa, A.; Terada, M.; Takayama, H.; Nakagawa, K.; Okano, T. BINOL-Ti-Catalized Carbonyl-Ene Cyclization by Tuning the 6-Br-Ligand for the Synthesis of 2-Methyl-19-nor-22-oxa Vitamin D Analogue with Significant Differentiation Activity. Synlett 1999, 1899-1902.
76. Shimizu, M.; Iwasaki, Y.; Shibamoto, Y.; Sato, M.; DeLuca, H. F.; Yamada, S. Novel Synthesis of 2-Substituted 19-Norvitamin D A-Ring Phosphine Oxide from D-Glucose as a Building Block Bioorg. Med. Chem. Lett. 2003, 13, 809-812.
77. Shimizu, M.; Yamamoto, K.; Mihori, M.; Iwasaki, Y.; Morizono, D.; Yamada, S. Two-dimensional Alanine Scanning Mutational Analysis of the Interaction between the Vitamin D Receptor and Its Ligands: Studies of A-Ring Modified 19-Norvitamin D Analogs. J. Steroid Biochem. Mol. Biol. 2004, 89-90, 75-81.
78. Zhou, X.; Zhu, G.-D.; Van Haver, D.; Vandewalle, M.; De Clercq, P. J.; Verstuyf, A.; Bouillon, R. Synthesis, Biological Activity, and Conformational Analysis of Four Seco-D-15,19-bisnor-1α,25-dihydroxyvitamin D Analogues, Diastereomeric at C17 and C20. J. Med. Chem. 1999, 42, 3539-3556.
79. 3 to its 1,25-Dihydroxy Metabolite. Tetrahedron Lett. 1991, 32, 6057-6060.
80. 3. Bioorg. Med. Chem. Lett. 1995, 5, 159-162.
81. 3 Derivative. Tetrahedron 2001, 57, 681-694.
82. Baudin, J. B.; Hareau, G.; Julia, S. A.; Ruel, O. A Direct Synthesis of Olefins by Reaction of Carbonyl Compounds With Lithio Derivatives of 2-[Alkyl- or (2'-Alkenyl)- or Benzyl-sulfonyl]-Benzothiazoles. Tetrahedron Lett. 1991, 32, 1175-1178.
83. 3: A-Ring Structural Motif that Modulates Interactions of Vitamin D Receptor with Transcriptional Coactivators. Org. Biomol. Chem. 2003, 1, 1863-1869.
84. 3, the Potent Inducers of Cell Differentiation. J. Steroid Biochem. Mol. Biol. 2004, 89-90, 89-92.
85. 3: Chemistry and Biology. Bioorg. Med. Chem. 2002, 10, 2353-2365.
86. 3 with Two Substituents at C-2: Synthesis and Biological Activity. Bioorg. Med. Chem. Lett. 2005, 15, 1451-1455.
87. 3 analogs, see: Zhu, G.-D.; Okamura, W. H. Synthesis of Vitamin D (Calciferol). Chem. Rev. 1995, 95, 1877-1952.
88. 3. Biochemistry 1984, 23, 1473-1478.
89. 3 under Physiological Conditions. Vitamin D: Molecular, Cellular and Clinical Endocrinology; Norman, A. W.; Schaefer, K.; Grigoleit, H. G.; von Herrath, D.; Eds.; Walter de Gruyter: Berlin, 1988, pp. 143-144.
90. 3. J. Biol. Chem. 1999, 274, 16392-16399.
91. 3 Analogue Toward Vitamin D Receptor Function. J. Biol. Chem. 1999, 274, 32376-32381.
92. 3-26,23-lactone Analogs Antagonize Differentiation of Human Leukemia Cells (HL-60 Cells) but not of Human Acute Promyelocytic Leukemia Cells (NB4 Cells). FEBS Lett. 1999, 460, 297-302.
93. 3 in Human Promyelocytic Leukemia (HL-60) Cells. Arch. Biochem. Biophys. 2000, 380, 92-102.
94. 3. Endocrinol. 2001, 142, 59-67.
95. 3. Steroids 2001, 66, 227-237.
96. 3 Receptor for the Partial Agonism of Carboxylic Ester Antagonists. J. Mol. Biol. 2002, 315, 229-238.
97. Carlberg, C. Molecular Basis of the Selective Activity of Vitamin D Analogues. J. Cell. Biochem. 2003, 88, 274-281.
98. Recent review on the function of VDR in response to 1 and other synthetic ligands, see: Carlberg, C. Current Understanding of the Function of the Nuclear Vitamin D Receptor in Response to Its Natural and Synthetic Ligands. In VitaminD Analogs in Cancer Prevention and Therapy, Recent Results in Cancer Research 164; Reichrath, J., Friedrich, M., Tilgen, M.; Eds.; Springer: Berlin, 2003; pp. 29-42.
99. Carlberg, C. Ligand-Mediated Conformational Changes of the VDR Are Required for Gene Transactivation. J. Steroid Biochem. Mol. Biol. 2004, 89-90, 227-232.
100. 3-26,23S-lactone Antagonizes the Nuclear Vitamin D Receptor by Mediating a Unique Noncovalent Conformational Change. Mol. Endocrinol. 2000, 14, 1788-1796.
101. Ochiai, E.; Miura, D.; Eguchi, H.; Takenouchi, K.; Harada, Y.; Azuma, Y.; Kamimura, T.; Ishizuka, S. Antagonistic Actions of TEI-9647 Depend on the Primary Structure of AF-2 domain of Vitamin D Receptors. J. Bone Miner. Res. 2003, 18 (suppl. 2), S103.
102. Ochiai, E.; Miura, D.; Eguchi, H.; Ohara, S.; Takenouchi, K.; Azuma, Y.; Kamimura, T.; Norman, A. W.; Ishizuka, S. Molecular Mechanism of the Vitamin D Antagonistic Actions of (23S)-25-Dehydro-1α-hydroxyvitamin D3-26,23-lactone Depends on the Primary Structure of the Carboxyl-Terminal Region of the Vitamin D Receptor. Mol. Endocrinol. 2005, 19, 1147-1157.
103. Peräkylä, M.; Molnár, F.; Carlberg, C. A Structural Basis for the Species-Specific Antagonism of 26,23-Lactones on Vitamin D Signaling. Chem. Biol. 2004, 11, 1147-1156.
104. 3 Antagonists. J. Steroid Biochem. Mol. Biol. 2004, 89-90, 31-34.
105. Some biologically active natural products having an α-methylene-γ-lactone structure react with the thiol group of cysteine to give the corresponding cysteine adduct: Kupchan, S. M.; Fessler, D. C.; Eakin, M. A.; Giacobbe, T. J. Reactions of alpha Methylene Lactone Tumor Inhibitors with Model Biological Nucleophiles. Science 1970, 168, 376-378.
106. 3-26,23-lactones. Org. Biomol. Chem. 2003, 1, 4396-4402.
107. 3 Library in the Solid-Phase. J. Am. Chem. Soc. 2001, 123, 3716-3722.
108. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. High-Field FT NMR Application of Mosher's Method. The Absolute Configurations of Marine Terpenoids. J. Am. Chem. Soc. 1991, 113, 4092-4096.
109. Eisman, J. A.; Hamstra, A. J.; Kream, B. E.; DeLuca H. F. A Sensitive, Precise, and Convenient Method for Determination of 1,25-Dihydroxyvitamin D in Human Plasma. Arch. Biochem. Biophys. 1976, 176, 235-243.
110. Inaba, M.; DeLuca, H. F. Stabilization of 1,25-Dihydroxyvitamin D-3 Receptor in the Human Leukemia Cell Line, HL-60, with Diisopropylfluorophosphate. Biochim. Biophys. Acta 1989, 1010, 20-27.
111. Fujishima, T.; Kojima, Y.; Azumaya, I.; Kittaka, A.; Takayama, H. Design and Synthesis of Potent Vitamin D Receptor Antagonists with A-Ring Modifications: Remarkable Effects of 2α-Methyl Introduction on Antagonistic Activity. Bioorg. Med. Chem. 2003, 11, 3621-3631.
112. Recent reviews on Paget's bone disease, see: Reddy, S. V. Etiology of Paget's Disease and Osteoclast Abnormalities. J. Cell Biochem. 2004, 93, 688-696.
113. Roodman, G. D.; Windle, J. J. Paget Disease of Bone. J. Clin. Invest. 2005, 115, 200-208.
114. Reddy, S. V.; Kurihara, N.; Menaa, C.; Roodman, G. D. Paget's Disease of Bone: a Disease of the Osteoclast. Rev. Endocr. Metab. Disord. 2001, 2, 195.
115. 3 and Their 20-Epimers: Possible Binding Modes of Potent A-Ring Analogues to Vitamin D Receptor. Chem. Biol. 2001, 8, 1011-1024.
116. 3 Analogues Containing Amide Bond. Bioorg. Med. Chem. Lett. 2002, 12, 3533-3536.
117. Swamy, N.; Addo, J. K.; Ray, R. Development of an Affinity-driven Cross-linker: Isolation of a Vitamin D Receptor Associated Factor. Bioorg. Med. Chem. Lett. 2000, 10, 361-364.
118. 3 Faces Outward in the Vitamin D Sterol-Binding Pocket of Vitamin D-Binding Protein. Bioorg. Med. Chem. Lett. 2002, 12, 279-281.
119. 3. Bioorg. Med. Chem. 2004, 12, 5443-5451.