Inhibitors of 25-hydroxyvitamin D3-1α-hydroxylase: A-ring oxa analogs of 25-hydroxyvitamin D31

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5617-5625

  Daniel, Dilon ^a   Middleton, Rondo ^b   Henry, Helen L ^b   Okamura, William H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 DEOXY 25 HYDROXY A HOMO 2 OXAVITAMIN D3; COLECALCIFEROL DERIVATIVE; ENZYME INHIBITOR; OXYGENASE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CHICKEN; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; KIDNEY; NONHUMAN;

EID: 0029763337     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960498g     Document Type: Article

References (33)

1. (a) Studies of Vitamin D (Calciferol) and Its Analogues. 50. Part 49: Fernàndez, S.; Ferrero, M.; Gotor, V.; Okamura, W. H. Selective Acylation of A-Ring Precursors of Vitamin D Using Enzymes in Organic Solvents J. Org. Chem. 1995, 60, 6057-6061.
2. 3-1α-Hydroxylase: A-Ring Analogs. In Vitamin D, A Pluripotent Steroid Hormone: Structural Studies, Molecular Endocrinology and Clinical Applications; Norman, A. W., Bouillon, R., Thomasset, M., Eds.; Walter de Gruyter: Berlin, 1994; pp 35-36.
3. (a) Bouillon, R.; Okamura, W. H.; Norman, A. W. Structure-Function Relationships in the Vitamin D Endocrine System. Endocrine Rev. 1995, 16, 200-257.
4. (b) Zhu, G.-D.; Okamura, W. H. Synthesis of Vitamin D (Calciferol). Chem. Rev. 1995, 95, 1877-1952.
5. (a) Henry, H. L. Vitamin D Hydroxylases J. Cell. Biochem. 1992, 49, 4-9.
6. (b) Henry, H. L.; Tang, C.; Blanchard, R.; Marchetto, G. S. Regulation of the Ferredoxin Component of Renal Hydroxylases at Transcriptional and Postranslational Levels and of the Protein Inhibitor of Cyclic AMP-dependent Kinase. J. Steroid Biochem. Molec. Biol. 1995, 53, 595-598.
7. 3 and Its 1β-Epimer: Synthesis and Biological Evaluation. J. Org. Chem. 1992, 57, 3846-3854.
8. 3. J. Am. Chem. Soc. 1982, 104, 6105-6109.
9. (c) Enas, J. D.; Shen, G.-Y.; Okamura, W. H. [1,7]-Sigmatropic Hydrogen Shifts of A-Norvitamin D Analogues: Ring Size and Substituent Effects on the Previtamin D - Vitamin D Equilibrium. J. Am. Chem. Soc. 1991, 113, 3873-3881.
10. (d) Enas, J. D.; Palenzuela, J. A.; Okamura, W. H. A-Homo-11-hydroxy-3-deoxy- vitamin D: Ring Size and π-Facial Selectivity Effects on the [1,7]-Sigmatropic Hydrogen Shift of Previtamin D to Vitamin D. J. Am. Chem. Soc. 1991, 113, 1355-1363.
11. (e) Unsuccessful attempts (Okamura, W. H.; Maestro, M.; Mourino, A. Unpublished observations) to prepare 5b are summarized in: Maestro, M. A. Synthesis of Analogs and Inhibitors of Vitamin D. Ph.D. Thesis, Department of Chemistry, University of Santiago de Compostela, Spain, 1989.
12. 3 Metabolism in Cultured Kidney Cells. J. Steroid Biochem. Molec. Biol. 1991, 38, 775-779.
13. (b) Barrack, S. A.; Gibbs, R. A.; Okamura, W. H. Potential Inhibitors of Vitamin D Metabolism: An Oxa Analogue of Vitamin D. J. Org. Chem. 1988, 53, 1790-1796.
14. (c) Okamura, W. H.; Shen, G.-Y.; Barrack, S. A.; Henry, H. L. Vitamin D Analogues: Potential Inhibitors of Vitamin D Metabolism. In Vitamin D: Molecular, Cellular and Clinical Endocrinology; Norman, A. W., Schaefer, K., Grigoleit, H.-G., Herrath, D. v., Eds.; Walter de Gruyter: Berlin, New York, 1988; pp 12-21.
15. (a) Okamura, W. H.; Midland, M. M.; Hammond, M. W.; Abd.Rahman, N.; Dormanen, M. C.; Nemere, I.; Norman, A. W. Chemistry and Conformation of Vitamin D Molecules. J. Steroid Biochem. Molec. Biol. 1995, 53, 603-613.
16. 3 Based on the Provitamin D Skeleton. Ann. N.Y. Acad. Sci. 1995, 761, 344-348.
17. 3. J. Am. Chem. Soc. 1991, 113, 6958-6966.
18. 3 (As a 6-s-Cis Analog) Stimulates Non-genomic But Not Genomic Biological Responses. J. Biol. Chem. 1993, 268, 13811-13819.
19. 3 Analogues: Stereoselective Preparation of 6β-Vitamin D Vinylallenes and a Concise Enynol Synthesis for Preparing the A-Ring. J. Org. Chem. 1989, 54, 4072-4083.
20. (a) 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.
21. (b) Trost, B. M.; Dumas, J. New Strategy for the Total Synthesis of 1α-Hydroxyvitamin D Derivatives. J. Am. Chem. Soc. 1992, 114, 1924-1925.
22. (c) Trost, B. M.; Dumas, J. Palladium-catalyzed Alkylative Cyclization Useful in Synthesis of Vitamin D and Analogs. PCT Int. 16, 022, 1993, US, 831, 687, 1992; Chem. Abstr. 1994, 120, 107474f.
23. (c) Trost, B. M.; Dumas, J. Palladium-catalyzed Alkylative Cyclization Useful in Synthesis of Vitamin D and Analogs. PCT Int. 16, 022, 1993, US, 831, 687, 1992; Chem. Abstr. 1994, 120, 107474f.
24. 3 via Diastereoselective Isopropylation and Alkylative Enyne Cyclization. Tetrahedron 1995, 51, 5543-5556.
25. (e) Trost, B. M.; Hanson, P. R. A Practical Asymmetric Synthesis of a 1,7-Enyne A-Ring Synthon En Route Toward the Total Synthesis of Vitamin D Analogues. Tetrahedron Lett. 1994, 35, 8119-8122.
26. 3.) Chem. Ber. 1957, 90, 664-673.
27. 3 to Its 1,25-Dihydroxy Metabolite. Tetrahedron Lett. 1991, 32, 6057.
28. 3: Synthesis, Isomerization to Previtamins, and Biological Studies. J. Med. Chem. 1994, 37, 2387.
29. (a) Harvey, D. F.; Lund, K. P.; Neil, D. A. Cyclization Reactions of Molybdenum and Chromium Carbene Complexes with 1,6- and 1,7-Enynes: Effect of Tether Length and Composition. J. Am. Chem. Soc. 1992, 114, 8424-8434.
30. (b) Padwa, A.; Krumpe, K. E.; Kassir, J. M. Rhodium Carbenoid Mediated Cyclizations of o-Alkynyl-Substituted α-Diazoacetophenones. J. Org. Chem. 1992, 57, 4940-4948.
31. (c) Billington, D. C.; Willison, D. A Simple Organocobalt Mediated Synthesis of Substituted 3-Oxabicyclo[3.3.0]oct-6-en-7-ones. Tetrahedron Lett. 1984, 25, 4041-4044.
32. Lee, G. C. M.; Tobias, B.; Holmes, J. M.; Harcourt, D. A.; Garst, M. E. A New Synthesis of Substituted Fulvenes. J. Am. Chem. Soc. 1990, 112, 9330-9336.
33. Silverman, R. B. Mechanism-based Enzyme Inactivation: Chemistry and Enzymology; CRC Press, Inc.: Boca Raton, FL, 1980; Vol. 1, pp 3-30.