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Analogues of prostacyclin (PGI2) modified in the 2-oxabicyclo[3.3.0]octane fragment (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A review is given of the synthetic analogs of the prostacyclins having greater chemical and metabolic stability than prostacyclin itself. Possible routes for synthesis are discussed.

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Literature cited

  1. S. Moncada, R. J. Gryglewski, S. Bunting, and J. R. Vane, Nature (London), 263, 663 (1976).

    Google Scholar 

  2. A. Szczeklik, R. J. Gryglewski, R. Nizankowski, J. Musial, R. Pieton, and J. Mruk, Pharmacol. Res. Commun., 10, 545 (1978).

    Google Scholar 

  3. E. W. Spannhake, A. L. Hyman, and P. J. Kadowitz, Prostaglandins, 22, 1013 (1981).

    Google Scholar 

  4. R. A. Johnson, D. R. Morton, J. H. Kinner, R. R. Gorman, J. C. McGuire, F. F. Sun, N. Whittaker, S. Bunting, J. Salmon, S. Moncada, and J. R. Vane, Prostaglandins, 12, 915 (1976).

    Google Scholar 

  5. E. J. Corey, G. E. Keck, and I. Székely, J. Am. Chem. Soc., 99, 2006 (1977).

    Google Scholar 

  6. R. A. Johnson, F. H. Lincoln, J. L. Thompson, E. G. Nidy, S. A. Mizsak, and U. Axen, J. Am. Chem. Soc., 99, 4182 (1977).

    Google Scholar 

  7. N. Whittaker, Tetrahedron Lett., No. 32, 2805 (1977).

    Google Scholar 

  8. I. Tömösközi, G. Galambos, V. Simonidesz, and G. Kovacs, Tetrahedron Lett., No. 30, 2627 (1977).

    Google Scholar 

  9. K. C. Nicolaou, W. E. Barnette, G. P. Gasic, R. L. Magolda, and W. J. Sipia, Chem. Commun., No. 18, 630 (1977).

    Google Scholar 

  10. E. J. Corey, I. Székely, and C. S. Shiner, Tetrahedron Lett., No. 40, 3529 (1977).

    Google Scholar 

  11. G. J. Dusting, S. Moncada, and J. R. Vane, Brit. J. Pharmacol., 64, 315 (1978).

    Google Scholar 

  12. Y. Chiang and A. J. Kresge, Chem. Communs., No. 2, 129 (1979).

    Google Scholar 

  13. J. Fried, D. K. Mitra, M. Nagarajan, and M. M. Mehotra, J. Med. Chem., 23, 234 (1980).

    Google Scholar 

  14. M. J. Cho and M. A. Alien, Prostaglandins, 15, 943 (1978).

    Google Scholar 

  15. G. J. Dusting, S. Moncada, and J. R. Vane, Brit. J. Pharmacol., 62, 414 (1978).

    Google Scholar 

  16. W. Bartmann and G. Beck, Angew Chem., Int. Ed., 21, 751 (1982).

    Google Scholar 

  17. S. Moncada and J. R. Vane, J. Med. Chem., 23, 541 (1980).

    Google Scholar 

  18. S. Moncada and J. R. Vane, Clin. Sci., 61, 369 (1981).

    Google Scholar 

  19. K. C. Nicolaou, G. P. Gasic, and W. E. Barnette, Angew Chem. Int. Ed., 17, 293 (1978).

    Google Scholar 

  20. W. E. Barnette, CRC Critical Reviews in Biochemistry, 15, No. 3, 201 (1984).

    Google Scholar 

  21. R. A. Johnson, D. R. Morton, and N. A. Nelson, Prostaglandins, 15, 737 (1978).

    Google Scholar 

  22. R. F. Newton, S. M. Roberts, and R. J. K. Taylor, Synthesis, 6, 449 (1984).

    Google Scholar 

  23. K. Kojima and K. Sakai, Tetrahedron Lett., No. 39, 3743 (1978).

    Google Scholar 

  24. C. Gandolfi, in: Symp. Chem. Biochem. Prostanoids, Salford, July, 1978.

    Google Scholar 

  25. C. Gandolfi, C., Passarotti. W. Fava. A. Fumagalli, F. Faustini, and R. Ceserani, Belgian Patent No. 873,731; Chem. Abstr., 92, 6137 (1980).

    Google Scholar 

  26. A. Barco, S. Benetti, G. P. Baradi, and C. Gandolfi, J. Org. Chem., 45, 4776 (1980).

    Google Scholar 

  27. K. C. Nicolaou, W. J. Sipio, R. L. Magolda, S. Seitz, and W. E. Barnette, Chem. Communs., No. 24, 1067 (1978).

    Google Scholar 

  28. D. R. Morton and F. C. Brokaw, J. Org. Chem., 44, 2880 (1979).

    Google Scholar 

  29. M. Shibasaki, J. Ueda, and S. Ikegami, Tetrahedron Lett., No. 5, 433 (1979).

    Google Scholar 

  30. M. Shibaski, K. Iseki, and S. Ikegami, Chem. Lett., No. 10, 1299 (1979).

    Google Scholar 

  31. A. Sugie, H. Shimomura, J. Katsube, and H. Jamamoto, Tetrahedron Lett., No. 28, 2607 (1979).

    Google Scholar 

  32. Y., Konishi, M. Kawamura, Y. Arai, and M. Hayashi, Chem. Lett., No. 11, 1437 (1979).

    Google Scholar 

  33. W. Skufaalla and H. Vorbrüggen, Angew Chem., 93, 1080 (1981).

    Google Scholar 

  34. M. Yamazaki, M. Shibasaki, and S. Ikegami, Chem. Lett., No. 9, 1245 (1981).

    Google Scholar 

  35. P. A. Aristoff, J. Org. Chem., 46, 1954 (1981).

    Google Scholar 

  36. Y. Konishi, M. Kawamura, Y. Igushi, Y. Arai, and M. Hajashi, Tetrahedron, 37, 4391 (1981).

    Google Scholar 

  37. K. Kojima, S. Amemiya, K. Koyama, K. Sakai, Chem. Pharm. Bull, 31, 3775 (1983).

    Google Scholar 

  38. N. Mongelli, O. Magni, R. Ceserani, and C. Gandolfi, in: Vth International Conference on Prostaglandins, Florence, Fondazione Lorenzini (1982), p. 126.

    Google Scholar 

  39. D. R. Morton, US Patent No. 4,238,414; Chem. Abstr., 91, 192907 (1979).

    Google Scholar 

  40. U. F. Axen, US Patent No. 4,001,300; Chem. Abstr., 86, 43266 (1977).

    Google Scholar 

  41. J. W. Aiken and R. J. Shebuski, Prostaglandins, 19, 629 (1980).

    Google Scholar 

  42. P. A. Aristoff, US Patent 4,306,075: Chem. Abstr., 96, 162, 421, 162,422 (1982).

    Google Scholar 

  43. J. C. Sih, J. Org. Chem., 47, 4311 (1982).

    Google Scholar 

  44. M. Shibasaki, Y. Torisawa, and S. Ikegami, Tetrahedron Lett., No. 33, 3493 (1983).

    Google Scholar 

  45. M. Shibasaki, K. Iseki, and S. Ikegami, Tetrahedron Lett., No. 2, 169 (1980).

    Google Scholar 

  46. T. Okazaki, M. Shibasaki, and S. Ikegami, Chem. Pharm. Bull, 32, 424 (1984).

    Google Scholar 

  47. K., Shimoji and M. Hajashi, Tetrahedron Lett., No. 13, 1255 (1980).

    Google Scholar 

  48. P. A. Aristoff and A. W. Harrison, Tetrahedron Lett., No. 20, 2067 (1982).

    Google Scholar 

  49. K. C. Nikalaou, W. E. Barnette, G. P., Gasic, and R. L. Magolda, J. Am. Chem. Soc., 99, 7737 (1977).

    Google Scholar 

  50. K. C. Nicolaou, W. E. Barnette, and R. L. Magolda, J. Am. Chem.Soc., 100, 2567 (1978).

    Google Scholar 

  51. K. G. Nikolaou, W. E. Barnette, and R. L. Magolda, J. Am. Chem. Soc., 103, 3472 (1981).

    Google Scholar 

  52. M. Shibasaki and S. Ikegami, Tetrahedron Lett., No. 6, 559 (1978).

    Google Scholar 

  53. S. Ikegami, M. Shibasaki, M. Mori, and T. Kanayama, Japanese Patent No. 7,966,667; Chem. Abstr., 90, 211254 (1979).

    Google Scholar 

  54. K. Shimoji, Y. Arai, and M. Hayashi, Chem. Lett., No. 12, 1375 (1978).

    Google Scholar 

  55. K. C. Nicolaou, W. E. Barnette, and R. L. Magolda, J. Am. Chem. Soc., 103, 3486 (1981).

    Google Scholar 

  56. K. C. Nicolaou, R. L. Magolda, and W. E. Barnette, Chem. Commun., No. 9, 375 (1978).

    Google Scholar 

  57. M. Shibasaki, Y. Torisawa, and S. Ikegami, Chem. Lett., No. 10, 1247 (1980).

    Google Scholar 

  58. M. Shibasaki, Y. Torisawa, and S. Ikegami, Tetrahedron Lett., No. 44, 4607 (1982).

    Google Scholar 

  59. G. L. Bundy and J. M. Baldwin, Tetrahedron Lett., No. 16, 1371 (1978).

    Google Scholar 

  60. W. Bartmann, G. Beck, J. Knolle, R. H. Rupp, Angew Chem., Int. Ed., 19, 819 (1980).

    Google Scholar 

  61. W. Bartmann, G. Beck, J. Knolle, and R. H. Rupp, Tetrahedron Lett., No. 36, 3647 (1982).

    Google Scholar 

  62. H. W. Smith, European Patent No. 29,341; Chem. Abstr., 95, 186711 (1981).

    Google Scholar 

  63. H. W. Smith, M. K. Bach, A. W. Harrison, H. G. Johnson, N. J. Major, and M. A. Waserman, Prostaglandins, 24, 543 (1982).

    Google Scholar 

  64. B. Radüchel, Tetrahedron Lett., No. 31, 3229 (1983).

    Google Scholar 

  65. M. Suzuki, S. Sugiura, and R. Noyori, Tetrahedron Lett., No. 46, 4817 (1982).

    Google Scholar 

  66. R. H. Bradbury and K. A. M. Walker, Tetrahedron Lett., No. 13, 1335 (1982).

    Google Scholar 

  67. R. H. Bradbury and K. A. M. Walker, J. Org. Chem., 48, 1741 (1983).

    Google Scholar 

  68. H. Nakai, Y. Arai, N. Hamanaka, and M. Hajashi, Tetrahedron Lett., No. 9, 805 (1979).

    Google Scholar 

  69. S. Amemiya, K. Kojima, and K. Sakai, Chem. Pharm. Bull., 32, 805 (1984).

    Google Scholar 

  70. P. G. Baraldi, A. Barco, S. Benetti, C. A. Gandolfi, G. P. Pollini, and D. Simoni, Tetrahedron Lett., No. 44. 4871 (1983).

    Google Scholar 

  71. J. Wang Chia-Lin, Tetrahedron Lett., No. 5, 477 (1983).

    Google Scholar 

  72. F. Cassidy, R. W. More, G. Wootton, K. H. Baggaley, G. R. Geen, L. J. A. Jennings, and A, W. R. Tyrrell, Tetrahedron Lett., No. 3, 253 (1981).

    Google Scholar 

  73. P. Heath, J. Mann, E. B. Walsh, and A. H. Wadsworth, J. Chem. Soc., Perkin I, No. 11, 2675 (1983).

    Google Scholar 

  74. R. A. Johnson and E. G. Nidy, J. Org. Chem., 45, 3802 (1980).

    Google Scholar 

  75. W. Skuballa, Tetrahedron Lett., No. 34, 3261 (1980).

    Google Scholar 

  76. R. F. Newton and A. H. Wadsworth, J. Chem. Soc., Perkin I, No. 3, 823 (1982).

    Google Scholar 

  77. A. J. Dixon, J. K. Taylor, R. F. Newton, and A. Wadsworth, Tetrahedron Lett., No. 3, 327 (1982).

    Google Scholar 

  78. A. J. Dixon, J. K. Taylor, R. F. Newton, A. H. Wadsworth, and G. Klinkert, J. Chem. Soc., Perkin I, No. 9, 1923 (1982).

    Google Scholar 

  79. Ono Pharmaceutical Co. Ltd., Japanese Patent No. 8,102,979; Chem. Abstr., 95, 24814 (1981).

    Google Scholar 

  80. K. C. Nicolaou, W. E. Barnette, and R. L. Magolda, J. Am. Chem. Soc., 101, 766 (1979).

    Google Scholar 

  81. K. Shimoji, Y. Konishi, Y. Arai, M. Hajashi, and H. Yamamoto, J. Am. Chem. Soc., 100, 2547 (1978).

    Google Scholar 

  82. R. A. Johnson, F. H. Lincoln, E. G. Nidy, W. P. Schneider, J. L. Thompson, and U. Axen, J. Am. Chem. Soc., 100, 7690 (1978).

    Google Scholar 

  83. J. C. Sih and D. R. Graber, J. Org. Chem., 43, 3798 (1978).

    Google Scholar 

  84. K. C. Nikolaou and W. E. Barnette, Chem. Communs, No. 10, 331 (1977).

    Google Scholar 

  85. C. H. Lin and D. L. Alexander, J. Org. Chem., 47, 615 (1982).

    Google Scholar 

  86. K. Ohno and H. Nishijama, Tetrahedron Lett., No. 32, 3003 (1979).

    Google Scholar 

  87. R. C. Nicholson and H. Vorbrüggen, Tetrahedron Lett., No. 1, 47 (1983).

    Google Scholar 

  88. T. Toru, K. Watanabe, T. Oba, T. Tanaka, N. Okamura, K. Bannai, and S. Kurozumi, Tetrahedron Lett., No. 6, 2539 (1980).

    Google Scholar 

  89. K. Bannai, T. Toru, T. Oba, T. Tanaka, N. Okamura, K. Watanabe, and S. Kurozumi, Tetrahedron Lett., No. 15, 1417 (1981).

    Google Scholar 

  90. K. Bannai, T. Torn, T. Oba, T. Tanaka, N. Okamura, K. Watanabe, and S. Kurozumi, Tetrahedron, 39, 3807 (1983). Florence (1982), p. 519.

    Google Scholar 

  91. T. Toru, K. Bannai, T. Tanaka, N. Okamura, A. Hazato, Y. Okamiya, T. Naruchi, and S. Kurozumi, in: Vth. International Conference on Prostaglandins, Fondazione Lorenzini, Florence (1982), p. 519.

    Google Scholar 

  92. K. Bannai, T. Toru, T. Oba, T. Tanaka, N. Okamura, K. Watanabe, A. Hazato, and S. Kurozumi, Tetrahedron Lett., No. 36, 3707 (1982).

    Google Scholar 

  93. H. Nishijama and K. Ohno, Tetrahedron Lett., No. 36, 3481 (1979).

    Google Scholar 

  94. D. M. Jones and N. F. Wood, J. Chem. Soc., No. 12, 5400 (1964).

    Google Scholar 

  95. A. Kresge and Y. Chiang, J. Chem. Soc., B, No. 1, 53 (1967).

    Google Scholar 

  96. H. Vorbrüggen, W. Skuballa, B. Radüchel, W. Loser, O. Loge, B. Müller, and G. Mannesmann, FGR Patent, No. 2,753,244; Chem. Abstr., 91, 91250 (1979).

    Google Scholar 

  97. I. Tömöscözi, K. Kanal, P. Györy, and G. Kovacs, Tetrahedron Lett., No. 10, 1091 (1982).

    Google Scholar 

  98. G. Covacs, V. Simonidesz, I. Tömöscözi, P. Körmöczy, I. Székely, A. Papp-Behr, I. Stadler, L. Szekeres, and G. Papp, J. Med. Chem., 25, 105 (1982).

    Google Scholar 

  99. J. L. Moniot, R. T. Fox, P. W. Sprague, and M. F. Heslanger, US Patent No. 4,311,644; Chem. Abstr., 97, 38743 (1982).

    Google Scholar 

  100. J. Fried, Patent No. WO 81/01002 (BE 885 660); Chem. Abstr., 95, 168635 (1981).

    Google Scholar 

  101. G. Galambos, V. Simonidesz, I. Ivanics, and G. Kovacs, in: Vth International Conference on Prostaglandins, Fondazione Lorenzini, Florence (1982), p. 513.

    Google Scholar 

  102. G. Galambos, V. Simonidesz, I. Ivanics, K. Horvath, and G. Kovacs, Tetrahedron Lett., No. 12, 1281 (1983).

    Google Scholar 

  103. T. Ono, I. Shibasaka, J. Nokami, and S. Nakabayashi, Chem. Lett., No. 8, 1249 (1983).

    Google Scholar 

  104. V. I. Mel'nikova, K. K. Pivnitskii, S. A. Kudryashev, and N. G. Geling, Bioorg. Khim., 9, No. 1, 115 (1983).

    Google Scholar 

  105. V. V. Bezuglov and L. D. Bergel'son, Dokl. Akad. Nauk SSSR, 250, 468 (1980).

    Google Scholar 

  106. L. Nysted and R. Pappo, European Patent No. 62, 303; Chem. Abstr., 98, 71787 (1983).

    Google Scholar 

  107. E. G. Nidy and R. A. Johnson, Tetrahedron Lett., No. 27, 2375 (1978).

    Google Scholar 

  108. P. A. Grieco, Y. Yokoyama, K. C. Nicolaou, W. E. Barnette, J. B. Smith, M. Ogletree, and A. M. Lefer, Chem. Lett., No. 9, 1001 (1978).

    Google Scholar 

  109. K. C. Nicolaou, W. F. Barnette, R. L. Magolda, P. A. Grieco, W. Owens, C.-L. Wang, J. B. Smith, M. Ogletree, and A. M. Lefer, Prostaglandins, 16, 789 (1978).

    Google Scholar 

  110. M. Suzuki, A. Yanagisawa, and R. Noyori, Tetrahedron Lett., No. 11, 1187 (1983).

    Google Scholar 

  111. H. Yokomori, Y. Torisawa, M. Shibasaki, and S. Ikegami, Heterocycles, 18, 251 (1982).

    Google Scholar 

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This review is an expanded version of the plenary lecture of the authors at the 3rd All-Union Conference on Synthetic and Applied Studies of Prostaglandins [in Russian], Ufa (1984).

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 579–595, May, 1986.

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Freimanis, Y.F., Dikovskaya, K. Analogues of prostacyclin (PGI2) modified in the 2-oxabicyclo[3.3.0]octane fragment (review). Chem Heterocycl Compd 22, 471–485 (1986). https://doi.org/10.1007/BF00519522

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