2-Alkylidene analogs of 19-nor-1α,25-(OH)2D3: Synthesis and biological activity

Polish Journal of Chemistry

Volumn 80, Issue 4, 2006, Pages 573-585

  Siciński, Rafał R ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

19 norvitamins D; Calcemic activity; Vitamin D analogs; Vitamins D

Indexed keywords

EID: 33646008265     PISSN: 01375083     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Conference Paper

References (59)

1. Reichle H., Koeffler H.P. and Norman A.W., N. Engl. J. Med., 320, 980 (1989).
2. Blunt J.W., DeLuca H.F. and Schnoes H.K., Biochemistry, 7, 3317 (1968).
3. Holick M.F., Schnoes H.K., DeLuca H.F., Suda T. and Cousins R.J., Biochemistry, 10, 2799 (1971).
4. Norman A.W., Vitamin D, the Calcium Homeostatic Steroid Hormone, Ed. Academic Press, New York 1979, p. 37.
5. DeLuca H.F. and Schnoes H.K., Annu. Rev. Biochem., 53, 411 (1983).
6. DeLuca H.F., FASEB J., 2, 224 (1988).
7. Bouillon R., Okamura W.H. and Norman A.W., Endocr. Rev., 16, 200 (1995).
8. Jones G., Strugnell S.A. and DeLuca H.F., Physiol. Rev., 78, 1193 (1998).
9. Feldman D., Glorieux F.H. and Pike J.W., (Eds.), Vitamin D; Academic Press: San Diego, 1997.
10. First International Conference on Chemistry and Biology of Vitamin D Analogues, Steroids, 66 (special issue), 127 (2001).
11. Dai H. and Posner G.H., Synthesis, 1383 (1994).
12. Zhu G. and Okamura W.H., Chem. Rev., 95, 1877 (1995).
13. Posner G.H. and Kahraman M., Eur. J. Org. Chem., 3889 (2003).
14. Kabat M.M. and Radinov R., Curr. Opin. Drug Discovery Dev., 4, 808 (2001).
15. Perlman K.L., Siciński R.R., Schnoes H.K. and DeLuca H.F., Tetrahedron Lett., 31, 1823 (1990).
16. Paaren H.E., DeLuca H.F. and Schnoes H.K., J. Org. Chem., 45, 3253 (1980).
17. Paaren H.E., Schnoes H.K. and DeLuca H.F., J. Org. Chem., 48, 3819 (1983).
18. Bouillon R., Sarandeses L.A., Allewaert K., Zhao J., Mascarenas J.L., Mourino A., Vrielynck S., De Clercq P. and Vandewalle M., J. Bone Miner. Res., 8, 1009 (1993).
19. Perlman K.L. and DeLuca H.F., Tetrahedron Lett., 33, 2937 (1992).
20. Huang P., Sabbe K., Pottie M. and Vandewalle M., Tetrahedron Lett., 36, 8299 (1995).
21. Zhou S., Anne S. and Vandewalle M., Tetrahedron Lett., 37, 7637 (1996).
22. Mikami K., Osawa A., Isaka A., Sawa E., Shimizu M., Terada M., Kubodera N., Nakagawa K., Tsugawa N. and Okano T., Tetrahedron Lett., 39, 3359 (1998).
23. Evans S.R.T., Schwartz A.M., Shchepotin E.I., Uskokovic M. and Shchepotin I.B., Clin. Cancer Res., 4, 2869 (1998).
24. Kubota T., Koshizuka K., Koike M., Uskokovic M., Miyoshi I. and Koeffler H.P., Cancer Res., 58, 3370 (1998).
25. Van Gool M., Zhao X., Sabbe K. and Vandewalle M., Eur. J. Org. Chem., 2241 (1999).
26. Lee N.E., Williard P.G., Brown A.J., Campbell M.J., Koeffler H.P., Peleg S., Rao D.S. and Reddy G.S., Steroids, 65, 252 (2000).
27. Slatopolsky E., Finch J., Ritter C., Denda M., Morrissey J., Brown A. and DeLuca H.F., Am. J. Kidney Dis., 26, 852 (1995).
28. Llach F., Dialys. Transpl., 30, 654 (2001).
29. Pai A.B., Lin S., Arruda J.A.L. and Lau A.H., Int. J. Artif. Organs, 26, 484 (2003).
30. Perlman K.L., Swenson R.E., Paaren H.E., Schnoes H.K. and DeLuca H.F., Tetrahedron Lett., 32, 7663 (1991).
31. Siciński R.R., Perlman K.L. and DeLuca H.F., J. Med. Chem., 37, 3730 (1994).
32. Wecksler W.R. and Norman A.W., Steroids, 35, 419 (1980).
33. Siciński R.R., Prahl J.M., Smith C.M. and DeLuca H.F., J. Med. Chem., 41, 4662 (1998).
34. Kiegiel J., Wovkulich P.M. and Uskokovic M.R., Tetrahedron Lett., 32, 6057 (1991).
35. Siciński R.R. and DeLuca H.F., Bioorg. Med. Chem. Lett., 5, 159 (1995).
36. Binderup L., Latini S., Binderup E., Bretting C., Calverley M. and Hansen K., Biochem. Pharmacol., 42, 1569 (1991).
37. Shevde N.K., Plum L.A. Clagett-Dame M., Yamamoto H., Pike J.W. and DeLuca H.F., Proc. Natl. Acad. Sci. USA, 99, 13487 (2002).
38. Yamamoto H., Shevde N.K., Warrier A., Plum L.A., DeLuca H.F. and Pike J.W., J. Biol. Chem., 278, 31756 (2003).
39. Siciński R.R., Prahl J.M., Smith C.M. and DeLuca H.F., Steroids, 67, 247 (2002).
40. DeLuca H.F., Gowlugari S. and Siciński R.R., U.S. Pat. No. 6,774,251 (August 10, 2004).
41. Plum L.A., Prahl J.M., Ma X., Siciński R.R., Gowlugari S., Clagett-Dame M. and DeLuca H.F., Proc. Natl. Acad. Sci. USA, 101, 6900 (2004).
42. Okamura W.H., Midland M.M., Hammond M.W., Abd.Rahman N., Dormanen M.C., Nemere I. and Norman A.W., J. Steroid. Biochem. Molec. Biol., 53, 603 (1995).
43. Havinga E., Experientia, 29, 1181 (1973).
44. Wing R.M., Okamura W.H., Rego A., Pirio M.R. and Norman A.W., J. Am. Chem. Soc., 97, 4980 (1975).
45. Berman E., Friedman N., Mazur Y. and Sheves M., J. Am. Chem. Soc., 100, 5626 (1978).
46. Eguchi T. and Ikekawa N., Bioorg. Chem., 18, 19 (1990).
47. Eguchi T., Kakinuma K. and Ikekawa N., Bioorg. Chem., 19, 327 (1991).
48. Ishida H., Shimizu M., Yamamoto K., Iwasaki Y. and Yamada S., J. Org. Chem., 60, 1828 (1995).
49. Rochel N., Wurtz J.M., Mitschler A., Klaholz B. and Moras D., Moll. Cell, 5, 173 (2000).
50. Vanhooke J.L., Benning M.M., Bauer C.B., Pike J.W. and DeLuca H.F., Biochemistry, 43, 4101 (2004).
51. Siciński R.R., Rotkiewicz P., Koliński A., Sicińska W., Prahl J.M., Smith C.M. and DeLuca H.F., J. Med. Chem., 45, 3366 (2002).
52. Johnson F., Chem. Rev., 68, 375 (1968).
53. Nasipuri D., Stereochemistry of Organic Compounds, Wiley Eastern: New Delhi, 1991; pp. 270-271.
54. Suhara Y., Nihei K., Tanigawa H., Fujishima T., Konno K., Nakagawa K., Okano T. and Takayama H., Bioorg. Med. Chem. Lett., 10, 1129 (2000).
55. Suhara Y., Nihei K., Kurihara M., Kittaka A., Yamaguchi K., Fujishima T., Konno K., Miyata N. and Takayama H., J. Org. Chem., 66, 8760 (2001).
56. Głȩbocka A., Siciński R.R. and DeLuca H.F., J. Steroid Biochem. Mol. Biol., 89-90, 25 (2004).
57. DeLuca H.F., Siciński R.R., Głȩbocka A. and Plum L.A., US Pat. Appl. No 20040229851 (November 18, 2004).
58. Yoshida A., Ono K., Suhara Y., Saito N., Takayama H. and Kittaka A., Synlett, 8, 1175 (2003).
59. Ono K., Yoshida A., Saito M., Fuishima T., Honzawa S., Suhara Y., Kishimoto S., Sugiura T., Waku K., Takayama H. and Kittaka A., J. Org. Chem., 68, 7407 (2003).