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Phosphorylation of indoles (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Methods for the introduction of phosphorus-containing groupings into indole and its derivatives and the chemical properties and biological activity of phosphorylated indoles are examined.

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Literature cited

  1. R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York-London (1970).

    Google Scholar 

  2. F. G. Mann, in: Progress in Organic Chemistry, Vol. 4, London (1958), p. 217.

    Google Scholar 

  3. R. S. Edmundson, Indian J. Chem., 41, 1770 (1962).

    Google Scholar 

  4. G. Märkl, Angew. Chem., 77, 1109 (1965).

    Google Scholar 

  5. G. Märkl, F. Lieb, and A. Mess, Angew. Chem., 79, 947 (1967).

    Google Scholar 

  6. R. A. Heacock and S. Kasparek, Advances in Heterocyclic Chemistry, Vol. 10, (1969), p. 43.

    Google Scholar 

  7. F. G. Mann, The Heterocyclic Derivatives of Phosphorus, Arsenic, Antimony, and Bismuth, Vol. 2, New York-London (1970).

  8. D. Redmore, Chem. Rev., 71, 316 (1971).

    Google Scholar 

  9. Q. Mingoia, Gazz. Chim. Ital., 60, 144 (1930).

    Google Scholar 

  10. B. G. van den Boss, C. J. Schoot, M. J. Koopmans, and J. Meltzer, Rec. Trav. Chim., 80, 1040 (1961).

    Google Scholar 

  11. J. Meltzer, K. Wellinga, and B. G. van den Boss, US Patent No. 3111525 (1963); Chem. Abstr., 60, 9285 (1964).

    Google Scholar 

  12. A. I. Razumov, Material from the Fourth All-Union Colloquium on the Chemistry and Pharmacology of Indole Compounds [in Russian], Shtiintsa, Kishinev (1975), p. 7.

    Google Scholar 

  13. A. Katritzy and J. Lagowski, The Chemistry of Heterocyclic Compounds [Russian translation], Inostr. Lit., Moscow (1963), p. 179.

    Google Scholar 

  14. G. M. Badger, The Chemistry of Heterocyclic Compounds, Academic Press, New York (1961), p. 64.

    Google Scholar 

  15. M. G. Reinecke, H. W. Johnson, and J. F. Sebastian, Tetrahedron Lett., 1183 (1963).

  16. J. C. Powers, W. P. Meyer, and T. G. Parsons, J. Am Chem. Soc., 89, 5812 (1967).

    Google Scholar 

  17. R. G. Pearson, Usp. Khim., 11, 1259 (1971).

    Google Scholar 

  18. B. A. Arbuzov, in: Reactions and Methods for the Study of Organic Compounds [in Russian], Moscow (1954), p. 3.

  19. D. Kh. Yarmukhametova, B. V. Kudryavtsev, and L. I. Anpilova, Tzv. Akad. Nauk SSSR, Ser. Khim., 435 (1974).

  20. A. I. Razumov and P. A. Gurevich, Zh. Obshch. Khim., 37, 1615 (1967).

    Google Scholar 

  21. A. I. Razumov and P. A. Gurevich, Trudy Kazansk. Khim.-Tekhnol. Institimeni S. M. Kirova 36, 480 (1967).

    Google Scholar 

  22. E. Fischer and T. Schmidt, Ber., 21, 1811 (1888).

    Google Scholar 

  23. V. A. Budylin, A. N. Kost, and E. D. Matveeva, Khim. Geterotsikl. Soedin., No. 1, 55 (1972).

    Google Scholar 

  24. V. A. Budylin, A. N. Kost, E. D. Matveeva, and V. I. Minkin, Khim. Geterotsikl. Soedin., No. 1, 68 (1972).

    Google Scholar 

  25. A. E. Torralba and T. C. Myers, J. Org. Chem., 22, 972 (1957).

    Google Scholar 

  26. F. Millich and E. J. Becker, J. Org. Chem., 23, 1096 (1958).

    Google Scholar 

  27. J. A. Eenkhoorn, O. S. de Silva, and V. Snieckus, Chem. Commun., 1095 (1970).

  28. J. A. Eenkhoorn, O. S. de Silva, and V. Snieckus, Can. J. Chem., 51, 792 (1973).

    Google Scholar 

  29. T. Kametani, T. Yamanaka, K. Nyu, and S. Takano, Yakugaku Zasshi, 91, 1033 (1971); Chem. Abstr., 75, 151626 (1971).

    Google Scholar 

  30. A. N. Kost, L. G. Yudin, V. A. Budylin, and V. I. Minkin, Dokl. Akad. Nauk SSSR, 176, 1096 (1967).

    Google Scholar 

  31. J. E. Bloor and D. L. Breen, J. Am. Chem. Soc., 89, 6835 (1967).

    Google Scholar 

  32. Q. Mingoia, Gazz. Chim. Ital., 62, 333 (1932).

    Google Scholar 

  33. A. I. Razumov, P. A. Gurevich, S. Yu. Baigil'dina, T. V. Zykova, and R. A. Salakhutdinov, Zh. Obshch. Khim., 44, 2587 (1974).

    Google Scholar 

  34. J. C. Powers, J. Org. Chem., 31, 2627 (1966).

    Google Scholar 

  35. J. C. Powers, Tetrahedron Lett., 655 (1965).

  36. A. M. Kinnear and E. A. Perren, J. Chem. Soc., 3437 (1952).

  37. J. P. Clay, J. Org. Chem., 16, 852 (1951).

    Google Scholar 

  38. J. B. Conant, J. Amer. Chem. Soc., 39, 2679 (1917).

    Google Scholar 

  39. P. C. Crofts and G. M. Kosolapoff, J. Am. Chem. Soc., 75, 3379 (1953).

    Google Scholar 

  40. É. E. Nifant'ev, The Chemistry of Organophosphorus Compounds [in Russian], MGU, Moscow (1971), p. 255.

    Google Scholar 

  41. C. van der Westeringh and H. Veldstra, Rec. Trav. Chim., 77, 1096 (1958).

    Google Scholar 

  42. J. Szmuszkovicz, J. Amer. Chem. Soc., 80, 3782 (1958).

    Google Scholar 

  43. P. A. Gurevich, Master's Dissertation, Kazan (1967).

  44. J. Sato and J. Matsumoto, Takamine Kenkyusho Nempo, 11, 33 (1959).

    Google Scholar 

  45. M. Kunori, Nippon Kagaku Zasshi, 81, 1431 (1960).

    Google Scholar 

  46. R. J. Sundberg, J. Org. Chem., 30, 3604 (1965).

    Google Scholar 

  47. A. Mustafa, M. M. Sidky, and F. M. Soliman, Tetrahedron, 22, 393 (1966).

    Google Scholar 

  48. J. J. Pappas and E. Gancher, J. Heterocycl. Chem., 6, 265 (1969).

    Google Scholar 

  49. E. Zbiral and L. Berner-Fenz, Monatsh., 98, 666 (1967).

    Google Scholar 

  50. D. Purdela and R. Vilceanu, The Chemistry of Organic Phosphorus Compounds [in Russian], Moscow (1972), pp. 228, 229.

  51. N. F. Albertson, US Patent No. 2980692 (1961); Chem. Abstr., 56, 457 (1962).

    Google Scholar 

  52. A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, USSR Author's Certificate No. 422740 (1972); Byul. Izobr., No. 13, 93 (1974).

  53. A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, Zh. Obshch. Khim., 44, 2586 (1974).

    Google Scholar 

  54. A. I. Razumov, P. A. Gurevich, S. Yu. Baigil'dina, and M. V. Alparova, Zh. Obshch. Khim., 44, 2585 (1974).

    Google Scholar 

  55. A. I. Razumov, P. A. Gurevich, R. I. Tarasova, and S. Yu. Baigil'dina, Zh. Obhsch. Khim., 46, 33 (1976).

    Google Scholar 

  56. B. P. Lugovkin, Zh. Obhsch. Khim., 43, 1261 (1973).

    Google Scholar 

  57. S. Hünig and H.-C. Steinmetzer, Tetrahedron Lett., 643 (1972).

  58. M. J. Gallagher and F. G. Mann, J. Chem. Soc., 4855 (1963).

  59. K. C. Srivastava and K. D. Berlin, J. Org. Chem., 37, 4487 (1972).

    Google Scholar 

  60. C. Janofsky and M. Rachmeler, Biophys. Acta, 28, 640 (1958).

    Google Scholar 

  61. O. Smith and C. Janofsky, J. Biol. Chem., 235, 2051 (1960).

    Google Scholar 

  62. C. Lingens and W. Lück, Z. Physiol. Chem., 333, 190 (1963).

    Google Scholar 

  63. A. A. P. G. Archer and J. Harley-Mason, Proc. Chem. Soc., 285 (1958).

  64. M. N. Preobrazhenskaya, K. V. Kholodkovskaya, E. G. Balashova, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 1, 28 (1967).

    Google Scholar 

  65. P. G. Zherebchenko, N. N. Suvorov, and V. S. Murashova, Med. Radiol., 27 (1961).

  66. V. A. Chernov, S. M. Volodarskaya, and L. G. Lytkina, Vopr. Onkol., 10, 76 (1964).

    Google Scholar 

  67. N. N. Suvorov, V. A. Chernov, L. M. Morozovskaya, and S. M. Volodarskaya, USSR Author's Certificate No. 168294 (1963); Byul. Izobr., No. 4, 27 (1965).

  68. L. M. Morozovskaya, N. N. Suvorov, M. A. Kolesnikova, V. A. Chernov, and S. M. Volodarskaya, in: The Chemistry of Organic Phosphorus Compounds [in Russian], Nauka, Leningrad (1967), p. 223.

    Google Scholar 

  69. A. I. Razumov, P. A. Gurevich, R. L. Yafarova, and L. A. Monakhova, USSR Author's Certificate No. 362025 (1971); Byul. Izobr., No. 2, 54 (1973).

  70. G. I. Zhungietu, F. N. Chukhrii, and A. I. Tolmachev, Zh. Vese. Khim. O-va, 15, 590 (1970).

    Google Scholar 

  71. A. K. Sheinkman, G. V. Samoilenko, S. N. Baranov, and P. A. Gurevich, USSR Author's Certificate No. 407900 (1971); Byul. Izobr., No. 47, 83 (1973).

  72. A. K. Sheinkman, G. V. Samoilenko, and N. A. Klyuev, Zh. Obshch. Khim., 44, 1472 (1974).

    Google Scholar 

  73. A. K. Sheinkman, Khim. Geterotsikl. Soedin., No. 1, 3 (1974).

    Google Scholar 

  74. A. K. Sheinkman, G. V., Samoilenko, and S. N. Baranov, The Chemistry and Applications of Organophosphorus Compounds [in Russian], Nauka, Moscow (1974), p. 366.

    Google Scholar 

  75. A. Hofmann, Experientia, 14, 397 (1958).

    Google Scholar 

  76. A. Hofmann, R. Heim, A. Brack, H. Kobel, A. Frey, H. Ott, T. Potrzilka, and F. Trohler, Helv. Chim. Acta, 42, 1557 (1959).

    Google Scholar 

  77. D. F. Downing, Quart. Rev., 16, 144 (1962).

    Google Scholar 

  78. N. N. Yarovenko, Zh. Vses. Khim. O-va, 4, 448 (1964).

    Google Scholar 

  79. L. M. Morozovskaya, M. A. Kolesnikova, and N. N. Suvorov, Zh. Obshch. Khim., 38, 2788 (1968).

    Google Scholar 

  80. N. N. Suvorov, L. M. Morozovskaya, and G. N. Tsvetkova, USSR Author's Certificate No. 191564 (1966); Byul. Izobr., No. 4, 35 (1967).

  81. V. P. Shamshin, V. F. Shner, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 4, 498 (1972).

    Google Scholar 

  82. V. P. Shamshin, V. F. Shner, and N. N. Suvorov, Zh. Obshch. Khim., 41, 537 (1971).

    Google Scholar 

  83. V. P. Shamshin, V. F. Shner, and N. N. Suvorov, Zh. Vses. Khim. O-va, 4, 474 (1969).

    Google Scholar 

  84. V. P. Shamshin, V. F. Shner, and N. N. Suvorov, The Chemistry and Applications of Organophosphorus Compounds [in Russian], Nauka, Moscow (1974), p. 363.

    Google Scholar 

  85. K. S. Tsou, H. C. F. Su, D. J. R. Heymann, and A. M. Seligman, J. Med. Chem., 10, 662 (1967).

    Google Scholar 

  86. J. P. Horwitz, C. V. Easwaran, and P. L. Wolf, Biochem. Biophys. Acta, 276, 206 (1972).

    Google Scholar 

  87. S. Umezawa, K. Tatsuta, O. Izawz, and T. Tsuchiya, Tetrahedron Lett. 97 (1972).

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Authors and Affiliations

  1. S. M. Kirov Kazan Chemical-Engineering Institute, USSR

    A. I. Razumov, P. A. Gurevich & S. Yu. Baigil'dina

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  1. A. I. Razumov
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  2. P. A. Gurevich
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  3. S. Yu. Baigil'dina
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 867–878, July, 1976

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Razumov, A.I., Gurevich, P.A. & Baigil'dina, S.Y. Phosphorylation of indoles (review). Chem Heterocycl Compd 12, 723–732 (1976). https://doi.org/10.1007/BF00476997

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  • DOI: https://doi.org/10.1007/BF00476997

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