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15th Anniversary of the synthesis of the first fluorine analogue of vitamin D3 chemical and biological aspects of the problem

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Chemistry of Natural Compounds Aims and scope

Abstract

A review of literature information and the results of investigations by the authors on methods of synthesis for, and the biological activity of, fluorine derivatives of vitamin D3 expands traditional idea on their influence on the regulation of Ca and P metabolism in the organism. The review includes literature sources from 1974 to 1989.

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Literature cited

  1. A. W. Norman, K. Schaefer, H.-G. Grigoleit, and D. V. Herrath, Vitamin D: Chemical, Biochemical and Clinical Update. Proceedings of the Sixth Workshop on Vitamin D, Merano, Italy, March (1985), Walter de Gruyter, Berlin (1985).

    Google Scholar 

  2. A. A. Wettstein, Ciba Foundation Symposium, Elsevier, New York (1973), p. 960.

    Google Scholar 

  3. A. A. Akhrem, I. G. Reshetova, and Yu. A. Titov, Usp. Khim.,34, No. 12, 2171–2205 (1965).

    Article  CAS  Google Scholar 

  4. V. M. Klimashevs'skii, R. I. Yakhimovich, and P. V. Vendt, Ukr. Biokhim. Zh.,46, No. 5, 627–630 (1974).

    Google Scholar 

  5. A. W. Norman, Vitamin D, Basic Research and its Clinical Application, Walter de Gruyter, Berlin (1979), p. 1318.

    Google Scholar 

  6. R. Filler and Y. Kobayashi, Biomedicinal Aspects of Fluorine Chemistry, Elsevier Biochemical Press, New York (1982).

    Google Scholar 

  7. Y. Kobayashi, Synthesis and Biological Activities of Fluorinated Vitamin D. The 3rd Regular Meeting of Soviet-Japanese Chemists, Tokyo, May 8–9 (1983), pp. 121–132.

  8. N. Ishikawa, Kagaku To Seibutsu,22, 93–103 (1984).

    Article  CAS  Google Scholar 

  9. Y. Kabayashi and T. Taguchi, J. Syn. Org. Chem. Jpn.,43, No. 11, 1073–1082 (1985).

    Article  Google Scholar 

  10. J. T. Welch, Tetrahedron,43, No. 10, 3123–3197 (1987).

    Article  CAS  Google Scholar 

  11. N. Ikekawa, J. Steroid Biochem.,19, No. 1C, 907–911 (1983).

    CAS  PubMed  Google Scholar 

  12. F. P. Ross, “Is Fluorine a Biologically Benign Replacement for Hydrogen in Vitamin D Analogs?” in: Proceedings of the Sixth Workshop on Vitamin D (1985), pp. 796–803.

  13. R. Pardo and M. Santelli, Bull. Soc. Chim. Fr., No. 1, 98–114 (1985).

  14. R. I. Yakhimovich and N. F. Fursaeva, Usp. Biol. Khim.,20, 192–213 (1979); V. K. Bauman, Prikl. Biokhim. Mikrobiol.,12, No. 6, 805–818 (1976); V. K. Baukman, N. A. Bogoslovskii, T. A. Kisel'nikova, M. K. Shakhova, M. Yu. Valinietse, D. A. Babarykin, and G. I. Samokhvalov, Prikl. Biokhim. Mikrobiol.,14, No. 2, 243–252 (1978).

    Google Scholar 

  15. R. I. Yakhimovich, Usp. Khim.,49, No. 4, 706–732 (1980).

    Article  CAS  Google Scholar 

  16. H. F. DeLuca and H. K. Schnoes, Annu. Rev. Biochem.,52, 411–439 (1983).

    Article  CAS  Google Scholar 

  17. M. R. Uskokovic, J. J. Partridge, T. A. Narwid, and E. G. Baggiolini, Basic Clinical Nutrition (1980), Part 2 (Vitamin D: Molecular Biology and Clinical Nutrition), pp. 1–57.

  18. R. Brommage and H. F. DeLuca, Endocr. Rev.,6, No. 4, 491–511 (1985).

    Article  CAS  Google Scholar 

  19. H. F. DeLuca and V. K. Östrem, Progr. Clin. Res.,259, 41–56 (1988).

    CAS  Google Scholar 

  20. J. M. Diamond, Nature,328, No. 6127, 199–200 (1988).

    Article  Google Scholar 

  21. M. J. Carverley, Tetrahedron,43, No. 20, 4609–4619 (1987).

    Article  Google Scholar 

  22. E. P. Amento, Steroids,49, No. 1–3, 55–72 (1987).

    Article  CAS  Google Scholar 

  23. W. F. C. Rigby, Immunol. Today,9, No. 2, 54–58 (1988).

    Article  CAS  Google Scholar 

  24. D. E. Ayer, Tetrahedron Lett., No. 23, 1065 (1962); L. A. Alekseeva, V. V. Bardin, and L. S. Boguslavskaya, New Fluorinating Agents in Organic Syntheses [in Russian], Nauka, Novosibirsk (1987), p. 257.

  25. M. Sheves, B. Sialom, and Y. Mazur, J. Chem. Soc. Chem. Commun.,13, 554–555 (1978).

    Article  Google Scholar 

  26. R. I. Yakhimovich, N. F. Fursaeva, and V. E. Pashinnik, Khim. Prir. Soedin., No. 4, 580–581 (1980).

  27. R. I. Yakhimovich, N. F. Fursaeva, and V. E. Pashinnik, Khim. Prir. Soedin., No. 1, 102–107 (1985).

  28. R. I. Yakhimovich and V. M. Klimashevs'kii, Usp. Biokhim. Zh.,46, No. 1, 124–127 (1974).

    Google Scholar 

  29. N. E. Boutin, D. U. Robert, and A. R. Cambon, Bull. Soc. Chim. Fr., No. 12, 2861–2863 (1974).

  30. R. I. Yakhimovich, N. F. Fursaeva, and G. M. Segal', Bioorg. Khim.,2, No. 11, 1526–1529 (1976).

    CAS  Google Scholar 

  31. R. I. Yakhimovich, V. M. Klimashevskii, and G. M. Segal', Khim.-Farm. Zh.,10, No. 3, 58–64 (1976).

    CAS  Google Scholar 

  32. L. K. Revelle, J. M. Londowski, B. S. Kost, and R. Kumar, J. Steroid Biochem.,22, No. 4, 269–274 (1985).

    Article  Google Scholar 

  33. J. L. Napoli, M. A. Fivizzani, H. K. Schnoes, and H. F. DeLuca, Biochemistry,18, No. 9, 1641–1646 (1979).

    Article  CAS  Google Scholar 

  34. E. Ohshima, S. Takatsuto, N. Ikekawa, and H. F. DeLuca, Chem. Pharm. Bull.,32, No. 9, 3518–3524 (1984).

    Article  CAS  Google Scholar 

  35. H. F. Paaren, M. A. Fivizzani, H. K. Schnoes, and H. F. DeLuca, Arch. Biochem. Biophys.,225, 649–654 (1983).

    Article  Google Scholar 

  36. British Patent No. 2026494 (1980); Chem. Abstr.,93, 204930 (1980).

  37. E. Ohshima, H. Sai, S. Takatsuto, N. Ikekawa, Y. Kobayashi, Y. Tanaka, and H. F. DeLuca, Chem. Pharm. Bull.,32, No. 9, 3525–3521 [sic] (1984).

    Article  CAS  Google Scholar 

  38. B. L. Onisko, H. K. Schnoes, and H. F. DeLuca, Tetrahedron Lett., No. 13, 1107–1108 (1977).

    Article  Google Scholar 

  39. S. Yang, C. Dorn, and H. Jones, Tetrahedron Lett., No. 27, 2315–2316 (1977).

  40. Y. Kobayashi, T. Taguchi, T. Tereada, J. Oshida, M. Morisaki, and N. Ikekawa, J. Chem. Soc. Perkin Trans. I, No. 1, 85–91 (1982).

  41. B. L. Onisko, H. K. Schnoes, and H. F. DeLuca, Bioorg. Chem.,9, No. 2, 187–198 (1980).

    Article  CAS  Google Scholar 

  42. J. L. Napoli, W. A. Fivizzani, A. H. Hamstra, H. K. Schnoes, H. F. DeLuca, and P. H. Stern, Steroids,32, No. 4, 2322–2334 (1978).

    Article  Google Scholar 

  43. J. L. Napoli, W. S. Mellon, M. A. Fivizzani, H. K. Schnoes, and H. F. DeLuca, J. Biol. Chem.,254, No. 6, 2017–2022 (1979).

    CAS  PubMed  Google Scholar 

  44. J. J. Partidge, S. J. Shiuey, A. Boris, J. P. Mallon, and M. R. Uskokovic, “Synthesis and biological activity of 24R-hydroxy-25-fluorocholecalciferol and 1α,24R-dihydroxy-25-fluorocholecalciferol,” in: Proceedings of the 4th Workshop in Vitamin D (1979), pp. 37–44.

  45. J. L. Napoli, W. S. Mellon, H. K. Schnoes, and H. F. DeLuca, Arch. Biochem. Biophys.,197, No. 1, 193–198 (1979).

    Article  CAS  Google Scholar 

  46. Y. Kobayashi, T. Taguchi, T. Terada, J. Oshida, M. Morisaki, and N. Ikekawa, Tetrahedron Lett.,22, 2023–2026 (1979).

    Article  Google Scholar 

  47. European Patent No. 73465 (1983); Chem. Abstr.,99, 71094 (1983).

  48. S. J. Shiuey, J. J. Partidge, and M. R. Uskokovic, J. Org. Chem.,53, No. 5, 1040–1046 (1988).

    Article  CAS  Google Scholar 

  49. Belgian Patent No. 897378 (1984); Chem. Abstr.100, 74003 (1984).

  50. S. Yamada, M. Ohmori, and H. Takayama, Tetrahedron Lett., No. 20, 1859–1862 (1979).

  51. S. Yamada, M. Ohmori, and H. Takayama, Chem. Pharm. Bull.,27, No. 12, 3196–3198 (1979).

    Article  CAS  Google Scholar 

  52. US Patent No. 4421690 (1983).

  53. US Patent No. 4201881 (1980); Chem. Abstr.93, 186685d (1980).

  54. D. V. Cohn, Calcium Regulation and Bone Metabolism: Basic and Clinical Aspects, (9th International Conference on Calcium Regulating Hormones and Bone Metabolism), Elsevier Science Publishers, New York (1987), p. 523.

    Google Scholar 

  55. US Patent No. 4619920 (1986); Chem. Abstr.106, 33388 (1986).

  56. Y. Kobayashi, T. Taguchi, N. Kanuma, N. Ikekawa, and Y. Oshida, Tetrahedron Lett.,22, No. 43, 4309–4312 (1981).

    Article  CAS  Google Scholar 

  57. Y. Kobayashi, T. Taguchi, N. Kanuma, N. Ikekawa, and Y. Oshida, J. Chem. Soc. Commun., No. 10, 459–460 (1980).

  58. Y. Kobayashi, T. Taguchi, S. Mitsuhasti, T. Eguchi, E. Oshima, and N. Ikekawa, Chem. Pharm. Bull.,30, No. 12, 4297–4303 (1982).

    Article  CAS  Google Scholar 

  59. Japanese Patent Application 61–254558 (1986); Chem. Abstr.,106, 84956 (1987).

  60. Japanese Patent Application 61–254599 (1986); Chem. Abstr.,106, 84955 (1987).

  61. M. Ohtsuka, Y. Fujimoto, and N. Ikekawa, Chem. Pharm. Bull.,34, No. 7, 2780–2785 (1986).

    Article  CAS  Google Scholar 

  62. T. Taguchi, S. Mitsuhashi, and A. Yamanouchi, Tetrahedron Lett.,25, No. 43, 4933–4936 (1984).

    Article  CAS  Google Scholar 

  63. M. Makada, Y. Tanaka, and H. F. DeLuca, Arch. Biochem. Biophys.,241, No. 1, 173–178 (1985).

    Article  Google Scholar 

  64. Belgian Patent No. 900385 (1984); Chem. Abstr.103, 123798 (1984).

  65. US Patent No. 4502991 (1985).

  66. US Patent No. 4552698 (1985).

  67. Y. Kobayashi, M. Nakezawa, I. Kumadaki, T. Taguchi, E. Ohshima, N. Ikewaka, T. Yanaka, and H. F. DeLuca, Chem. Pharm. Bull.,34, No. 4, 1568–1572 (1986).

    Article  CAS  Google Scholar 

  68. J. Oshida, M. Morisaki, and N. Ikekawa, Tetrahedron Lett.,21, No. 18, 1755–1756 (1980).

    Article  CAS  Google Scholar 

  69. USA Patent No. 4307025 (1981).

  70. B. Sialom and B. Mazur, J. Org. Chem.,45, No. 11, 2201–2204 (1980).

    Article  CAS  Google Scholar 

  71. W. G. Dauben, B. Kohler, and A. Roesle, J. Org. Chem.,50, No. 12, 2007–2010 (1985).

    Article  CAS  Google Scholar 

  72. European Patent No. 205285 (1986); Chem. Abstr.,106, 84957 (1986).

  73. N. Ikekawa, T. Eguchi, N. Hara, S. Takatsuto, A. Honda, Y. Mori, and S. Otomo, Chem. Pharm. Bull.,35, No. 10, 4362–4365 (1987).

    Article  CAS  Google Scholar 

  74. S. Yamada, K. Yamamoto, H. Naito, T. Suzuki, M. Ohmori, H. Takayama, Y. Shiina, C. Miyaura, H. Tanaka, E. Abe, T. Suda, I. Matsunaga, and Y. Nishii, J. Med. Chem.,28, No. 9, 1148–1153 (1985).

    Article  CAS  Google Scholar 

  75. A. Windaus and K. Buchholz, Chem. Ber.,72, 597 (1939).

    Article  Google Scholar 

  76. J. Strating, Rec. Trav. Chim.,71, 822 (1952).

    Article  CAS  Google Scholar 

  77. S. Bernstein and K. J. Sax, J. Org. Chem.,16, No. 5, 685–693 (1951).

    Article  CAS  Google Scholar 

  78. R. O. Yakhimovich, The Chemistry of the Vitamins D [in Russian], Naukova Dumka, Kiev (1978).

    Google Scholar 

  79. R. A. Corradino, N. Ikekawa, and H. F. DeLuca, Arch. Biochem. Biophys.,208, No. 1, 273–277 (1981).

    Article  CAS  Google Scholar 

  80. B. L. Onisko, H. K. Schnoes, H. F. DeLuca, and R. S. Glover, Biochem. J.,182, No. 1, 1–9 (1979).

    Article  CAS  Google Scholar 

  81. J. L. Napoli, M. A. Fivizzani, H. K. Schnoes, and H. F. DeLuca, Biochemistry,17, 2387 (1978).

    Article  CAS  Google Scholar 

  82. D. E. M. Lawson, N. Friedman, M. Scheves, and Y. Mazur, FEBS Lett.,80, 137 (1977).

    Article  CAS  Google Scholar 

  83. US Patent No. 4196133 (1980); Chem. Abstr.,93, 114841 (1980).

  84. P. H. Stern, Y. Tanaka, H. F. DeLuca, N. Ikekawa, and Y. Kobayashi, Mol. Pharmacol.,20, No. 3, 460–462 (1981).

    CAS  PubMed  Google Scholar 

  85. S. Okamoto, Y. Tanaka, H. F. DeLuca, S. Yamada, and H. Takayama, Arch. Biochem. Biophys.,206, No. 1, 8–14 (1981).

    Article  CAS  Google Scholar 

  86. S. Okamoto, Y. Tanaka, and H. F. DeLuca, “The biological activity of 24, 24-difluoro-1, 25-dihydroxyvitamin D in rats: a new vitamin D analog more potent than 1, 25-dihydroxyvitamin D3,” in: 63rd Annual Meeting of the Endocrine Society, Cincinnati, June 14–16 (1981).

  87. S. Okamoto, Y. Tanaka, H. F. DeLuca, Y. Kobayashi, and N. Ikekawa, Am. J. Physiol.,244, No. 2, E159-E163 (1983).

    CAS  PubMed  Google Scholar 

  88. B. D. Kabakoff, N. C. Kendrick, D. Faber, H. F. DeLuca, S. Yamada, and H. Takayama, Arch. Biochem. Biophys.,215, No. 2, 582–588 (1982).

    Article  CAS  Google Scholar 

  89. R. Corradino, H. F. DeLuca, Y. Tanaka, N. Ikekawa, and Y. Kobayashi, Biochem. Biophys. Res. Commun.,96, No. 4, 1800–1803 (1980).

    Article  CAS  Google Scholar 

  90. US Patent No. 4305880 (1981).

  91. Y. Tanaka, D. N. Pahuja, J. K. Wichmann, H. F. DeLuca, Y. Kobayashi, T. Taguchi, and N. Ikekawa, Arch. Biochem. Biophys.,218, No. 1, 134–141 (1982).

    Article  CAS  Google Scholar 

  92. Y. Tanaka, H. F. DeLuca, Y. Kobayashi, and N. Ikekawa, Arch. Biochem. Biophys.,229, No. 1, 348–354 (1984).

    Article  CAS  Google Scholar 

  93. M. F. Hollick, O. Kasten-Schraufrogel, T. Tavela, and H. F. DeLuca, Arch. Biochem. Biophys,166, No. 1, 63 (1975).

    Article  Google Scholar 

  94. US Patent No. 4500460 (1985).

  95. C. Kaneko, S. Yamada, A. Sugimoto, N. Ishikawa, T. Suda, M. Suzuki, and S. Sadaki, J. Chem. Soc. Perkin Trans. I, No. 12, 1104–1107 (1975).

    Article  Google Scholar 

  96. C. Kaneko, J. Snyth. Org. Chem. Jpn.,33, No. 2, 75–94 (1975).

    Article  CAS  Google Scholar 

  97. US Patent No. 4254045 (1981).

  98. R. Colston, M. J. Colston, and D. Feldman, Endocrinology,108, 1083–1086 (1981).

    Article  CAS  Google Scholar 

  99. E. Abe, C. Miyaura, J. Sakagami, M. Takeda, K. Konno, T. Yamazaki, S. Yoshiki, and T. Suda, Proc. Natl. Acad. Sci. USA,78, 4990–4999 (1981).

    Article  CAS  Google Scholar 

  100. G. Vanham, H. Van Baelen, B. K. Tan, and R. Bouillon, J. Steroid Biochem.,29, No. 4, 381–386 (1988).

    Article  CAS  Google Scholar 

  101. M. Inaba, K. Yukioka, Y. Nishizawa, S. Okuno, S. Otani, S. Morisawa, H. F. De Luca, H. Morii, Chem. Abstr.,108, 31410 (1988).

    Google Scholar 

  102. PCT Int. Patent Application 87–03282 (1987); Chem. Abstr.,107, 217935 (1987).

  103. B. K. Bauman, The Biochemistry and Physiology of Vitamin D [in Russian], Zinatne, Riga (1989), p. 480.

    Google Scholar 

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Institute of Bioorganic Chemistry and Petrochemistry, Academy of Sciences of the Ukrainian SSR, Kiev. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 707–732, November–December, 1990.

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Yakhimovich, R.I., Gogoman, I.V. & Bondarenko, L.B. 15th Anniversary of the synthesis of the first fluorine analogue of vitamin D3 chemical and biological aspects of the problem. Chem Nat Compd 26, 599–620 (1990). https://doi.org/10.1007/BF00630067

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