Skip to main content
SpringerLink
Log in

Pyrido[2,3-b]indoles (α-carbolines) (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Data on the methods for the synthesis of α-carbolines and on their physicochemical and biological properties are correlated.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. W. O. Kermack and J. E. McKail, in: Heterocyclic Compounds, Vol. 7, R. C. Elderfield, editor, Wiley, New York (1961), p. 344.

    Google Scholar 

  2. R. A. Abramovitch and I. D. Spenser, in: Advances in Heterocyclic Chemistry, Vol. 3, New York (1964), p. 79.

    Google Scholar 

  3. G. T. Tatevosyan, Anhydronium Bases of the Carboline Series [in Russian], Izd. Akad. Nauk Armyansk. SSR, Yerevan (1966).

    Google Scholar 

  4. B. Witkop, J. Am. Chem. Soc., 75, 3361 (1953).

    Google Scholar 

  5. A. J. Hubert, J. Chem. Soc.(D), Chem. Commun., No. 7, 328 (1969).

    Google Scholar 

  6. A. J. Hubert, J. Chem. Soc. (C), No. 10, 1334 (1969).

    Google Scholar 

  7. P. Natka-Namirskii and J. Kalinowski, Acta Pol. Pharm., 30, 1 (1973).

    Google Scholar 

  8. P. Natka-Namirski and J. Kalinowski, Acta Pol. Pharm., 27, 533 (1970).

    Google Scholar 

  9. P. Natka-Namirski and J. Kalinowski, Acta Pol. Pharm., 28, 219 (1971).

    Google Scholar 

  10. P. Natka-Namirski and J. Kalinowski, Acta Pol. Pharm., 31, 137 (1974).

    Google Scholar 

  11. P. Natka-Namirski and J. Kalinowski, Polish Patent No. 80610; Chem. Abstr., 86, 89787 (1977).

    Google Scholar 

  12. P. Natka-Namirski and J. Kalinowski, Polish Patent No. 72751; Chem. Abstr., 84, 17314 (1976).

    Google Scholar 

  13. P. Natka-Namirski, Pol. J. Pharmacol. Pharm., 30, 569 (1978).

    Google Scholar 

  14. R. A. Abramovitch, D. H. Hey, and R. D. Mulley, J. Chem. Soc., No. 12, 4263 (1954).

    Google Scholar 

  15. P. I. Abramenko, Zh. Vses. Khim. Ova., 18, 715 (1973).

    Google Scholar 

  16. V. M. Clark, A. Cox, and E. J. Herbert, J. Chem. Soc. (C), No. 7, 831 (1968).

    Google Scholar 

  17. K. H. Grellmann, J. M. Cherman, and H. Linschitz, J. Am. Chem. Soc., 85, 1881 (1963).

    Google Scholar 

  18. J. Bratt and H. Suschitzky, J. Chem. Soc. (D), Chem. Commun., No. 16, 949 (1972).

    Google Scholar 

  19. R. A. S. Smith and J. H. Boyer, J. Am. Chem. Soc., 73, 2626 (1951).

    Google Scholar 

  20. A. Da Settimo, G. Primofiore, V. Santerini, G. Biaggi, and L. D'Amico, Chim. Ind., 58, 878 (1976).

    Google Scholar 

  21. G. Smolinsky, J. Am. Chem. Soc., 82, 4717 (1960).

    Google Scholar 

  22. R. A. Abramovitch, I. Ahmad, and D. Newman, Tetrahedron Lett., No. 21, 752 (1961).

    Google Scholar 

  23. P. J. Bunyan and J. I. G. Cadogan, J. Chem. Soc., No. 1, 42 (1963).

    Google Scholar 

  24. N. N. Suvorov and V. P. Manaev, in: Reactions and Methods for the Investigation of Organic Compounds [in Russian], Vol. 9, Khimiya, Moscow (1959), p. 7.

    Google Scholar 

  25. S. Okuda and M. M. Robinson, J. Am. Chem. Soc., 81, 740 (1959).

    Google Scholar 

  26. L. N. Yakhontov, E. V. Pronina, and M. V. Rubtsov, Khim. Geterotsikl. Soedin., No. 4, 687 (1967).

    Google Scholar 

  27. L. N. Yakhontov, E. V. Pronina, and M. V. Rubtsov, Dokl. Akad. Nauk SSSR, 169, 361 (1966).

    Google Scholar 

  28. L. N. Yakhontov and E. V. Pronina, Khim. Geterotsikl. Soedin., No. 6, 1121 (1969).

    Google Scholar 

  29. L. N. Yakhontov, E. V. Pronina, and M. V. Rubtsov, Khim. Geterotsikl. Soedin., No. 2, 186 (1970).

    Google Scholar 

  30. A. H. Kelly and J. Parrick, Can. J. Chem., 44, 2455 (1966).

    Google Scholar 

  31. T. Yamazaki, K. Matoba, S. Imoto, and M. Terashima, Chem. Pharm. Bull., 24, 3011 (1976).

    Google Scholar 

  32. L. G. Yudin, A. N. Kost, and N. B. Chernyshova, Khim. Geterotsikl. Soedin., No. 4, 484 (1970).

    Google Scholar 

  33. P. A. Sharbatyan, A. N. Kost, V. V. Men'shikov, L. G. Yudin, and N. B. Chernyshova, Khim. Geterotsikl. Soedin., No. 9, 1227 (1980).

    Google Scholar 

  34. A. N. Kost, L. G. Yudin, and N. B. Chernyshova, Dokl. Akad. Nauk SSSR, 183, 112 (1968).

    Google Scholar 

  35. A. N. Kost, R. S. Sagitullin, and V. I. Gorbunov, Dokl. Akad. Nauk SSSR, 182, 838 (1968).

    Google Scholar 

  36. A. N. Kost, R. S. Sagitullin, V. I. Gorbunov, and N. N. Modyanov, Khim. Geterotsikl. Soedin., No. 3, 359 (1970).

    Google Scholar 

  37. R. S. Sagitullin, T. V. Mel'nikova, A. N. Kost, V. F. Snegirev, and E. N. Frenkel', Khim. Geterotsikl. Soedin., No. 8, 1043 (1973).

    Google Scholar 

  38. R. S. Sagitullin, T. V. Mel'nikova, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 10, 1436 (1974).

    Google Scholar 

  39. A. N. Kost, V. V. Men'shikov, and R. S. Sagitullin, Zh. Org. Khim., 12, 2234 (1976).

    Google Scholar 

  40. A. N. Kost, R. S. Sagitullin, T. Yagodzinski, and V. V. Men'shikov, Vestn. Mosk. Gos. Univ., Khim., 17, 618 (1976).

    Google Scholar 

  41. V. V. Men'shikov and R. S. Sagitullin, Zh. Vses. Khim. Ova., 27, 589 (1982).

    Google Scholar 

  42. R. S. Sagitullin, A. N. Kost, and N. N. Borisov, Khim. Geterotsikl. Soedin., No. 9, 1207 (1970).

    Google Scholar 

  43. N. N. Borisov, R. S. Sagitullin, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 1, 48 (1972).

    Google Scholar 

  44. R. S. Sagitullin, N. N. Borisov, A. N. Kost, and N. A. Simonova, Khim. Geterotsikl. Soedin., No. 1, 61 (1971).

    Google Scholar 

  45. R. S. Sagitullin, A. N. Kost, T. V. Mel'nikova, and P. A. Sharbatyan, Khim. Geterotsikl. Soedin., No. 7, 945 (1977).

    Google Scholar 

  46. R. S. Sagitullin, T. Yagodzinski, A. N. Kost, and V. V. Men'shikov, Khim. Geterotsikl. Soedin., No. 7, 925 (1978).

    Google Scholar 

  47. T. V. Mel'nikova, A. N. Kost, R. S. Sagitullin, and N. N. Borisov, Khim. Geterotsikl. Soedin., No. 9, 1273 (1973).

    Google Scholar 

  48. R. S. Sagitullin, A. N. Kost, E. D. Matveeva, and N. I. Nemudrova, Khim. Geterotsikl. Soedin., No. 7, 920 (1970).

    Google Scholar 

  49. A. N. Kost, R. S. Sagitullin, T. V. Mel'nikova, and G. V. Kaplun, Khim. Geterotsikl. Soedin., No. 10, 1368 (1972).

    Google Scholar 

  50. K. I. Kuchkova, A. A. Semenov, and I. V. Terent'eva, Khim. Geterotsikl. Soedin., No. 2, 197 (1970).

    Google Scholar 

  51. K. I. Kuchkova, E. P. Styngach, F. Sh. Rivilis, N. M. Frolova, and A. A. Semenov, Khim. Geterotsikl. Soedin., No. 3, 386 (1976).

    Google Scholar 

  52. V. V. Kononova, A. L. Vereschagin, V. M. Polyachenko, and A. A. Semenov, Khim.-farm. Zh., No. 12, 30 (1978).

    Google Scholar 

  53. V. V. Kononova, A. A. Semenov, E. G. Kirdei, A. P. Fedoseev, A. G. Bulavintsev, and V. I. Nechaev, Khim.-farm. Zh., No. 1, 60 (1981).

    Google Scholar 

  54. V. V. Kononova and A. A. Semenov, Izv. Sibirsk. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 3, 147 (1979).

    Google Scholar 

  55. A. N. Kost, G. A. Golubeva, M. K. Ostrovskii, and V. G. Zabrodnyaya, Khim. Geterotsikl. Soedin., No. 1, 69 (1977).

    Google Scholar 

  56. G. Winters and N. Di Mola, Tetrahedron Lett., No. 44, 3877 (1975).

    Google Scholar 

  57. M. Ebisawa and K. Nishi, Japanese Patent No. 8049377; Chem. Abstr., 93, 186322 (1980).

    Google Scholar 

  58. W. Borsche, M. Wagner-Roemmich, and J. Barthenheier, Ann. Chem., 550, 160 (1942).

    Google Scholar 

  59. V. V. Kononova and A. A. Semenov, Khim. Geterotsikl. Soedin., No. 9, 1211 (1982).

    Google Scholar 

  60. R. R. Burtner, US Patent No. 2690441; Chem. Abstr., 49, 13297 (1955).

    Google Scholar 

  61. L. Stephenson and W. K. Warburton, J. Chem. Soc. (C), No. 10, 1355 (1970).

    Google Scholar 

  62. J. Elks, G. B. Webb, G. J. Gregory, and J. D. Cocker, West German Patent No. 1913124; Chem. Abstr., 72, 43636 (1970).

    Google Scholar 

  63. L. Stephenson, W. K. Warburton, G. I. Gregory, J. D. Cocker, and V. M. Clark, British Patent No. 1268771; Chem. Abstr., 77, 48432 (1972).

    Google Scholar 

  64. L. Stephenson, W. K. Warburton, D. Gregory, and J. D. Cocker, West German Patent No. 1913120; Chem. Abstr., 74, 13126 (1971).

    Google Scholar 

  65. R. Eisenthal and A. R. Katritzky, Tetrahedron, 21, 2205 (1965).

    Google Scholar 

  66. J. W. Armit and R. Robinson, J. Chem. Soc., 127, 1604 (1925).

    Google Scholar 

  67. R. H. Freak and R. Robinson, J. Chem. Soc., II, 2013 (1938).

    Google Scholar 

  68. A. P. Gray, E. E. Spinner, and C. J. Cavallito, J. Am. Chem. Soc., 76, 2792 (1954).

    Google Scholar 

  69. L. Paoloni, Sci. Rep. Inst. Super. Sanit., 1, 86 (1961).

    Google Scholar 

  70. W. Lauson, W. H. Perkin, and T. Robinson, J. Chem. Soc., 125, 626 (1924).

    Google Scholar 

  71. R. A. Abramovitch, K. A. H. Adams, and A. D. Notation, Can. J. Chem., 38, 2152 (1960).

    Google Scholar 

  72. J. P. Saxena, J. Indian Chem. Soc., 45, 628 (1968).

    Google Scholar 

  73. A. P. Gray, J. Am. Chem. Soc., 77, 5970 (1955).

    Google Scholar 

  74. N. N. Pogodaeva, V. V. Kononova, and A. A. Semenov, Khim. Geterotsikl. Soedin., No. 8, 1074 (1979).

    Google Scholar 

  75. N. N. Pogodaeva, V. V. Kononova, E. I. Terskikh, and A. A. Semenov, Khim.-farm. Zh., No. 10, 32 (1981).

    Google Scholar 

  76. N. N. Pogodaeva, E. I. Terskikh, N. D. Ivanova, and A. A. Semenov, Khim.-farm. Zh., No. 12, 49 (1982).

    Google Scholar 

  77. P. J. Black and M. Z. Heffernan, Aust. Chem., 18, 353 (1965).

    Google Scholar 

  78. B. M. Mustedza and J. Parrick, J. Chem. Res. (S), No. 1, 43 (1980).

    Google Scholar 

  79. A. A. Polyakova and R. A. Khmel'nitskii, Mass Spectrometry in Organic Chemistry [in Russian], Khimiya, Leningrad (1972).

    Google Scholar 

  80. R. Herbert and D. G. Wibberby, J. Chem. Soc. (B), No. 3, 459 (1970).

    Google Scholar 

  81. T. B. O'Dell, C. Luna, and M. D. Napoli, J. Pharmacol. Exp. Ter., 114, 306 (1955).

    Google Scholar 

  82. V. Z. Gorkin, L. V. Tatyanenko, D. M. Krasnokut-skaya, E. V. Pronina, and L. N. Yakhontov, Biokhimiya, 32, 510 (1967).

    Google Scholar 

  83. P. Natka-Namirski, S. Kurzepa, J. Kazimierczyk, H. Kierylowicz, and M. Kobylinska, Acta Physiol. Pol., 17, 145 (1966).

    Google Scholar 

  84. K. Ishizumi and J. Katsube, Japanese Patent No. 7879899; Chem. Abstr., 89, 197519 (1978).

    Google Scholar 

  85. P. Natka-Namirski and L. Kaczmarek, Pol. J. Pharmacol. Pharm., 30, 569 (1978).

    Google Scholar 

  86. N. N. Pogodaeva and A. A. Semenov, Khim.-Farm. Zh. (in press).

  87. T. Okamoto, T. Akase, T. Izumi, S. Inaba, and H. Yamamoto, Japanese Patent No. 7220196; Chem. Abstr., 77, 152142 (1972).

    Google Scholar 

  88. J. Winters and N. Di Mola, West German Patent No. 2442513; Chem. Abstr., 82, 156255 (1975).

    Google Scholar 

  89. T. Matsumoto, Agric. Biol. Chem., 43, 675 (1979).

    Google Scholar 

  90. D. Ioshida, Biochem. Biophys. Res. Commun., 83, 915 (1978).

    Google Scholar 

  91. D. Ioshida and T. Matsumoto, Japanese Patent No. 8036401; Chem. Abstr., 93, 132377 (1980).

    Google Scholar 

  92. D. Ioshida and T. Matsumoto, Cancer Lett., 10, 141 (1980).

    Google Scholar 

  93. T. Kawachi, Hepato-gastroenterol., Supplement, 187 (1980).

Download references

Author information

Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, 664033, Irkutsk

    A. A. Semenov & V. V. Tolstikhina

Authors
  1. A. A. Semenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. V. Tolstikhina
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 435–447, April, 1984.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Semenov, A.A., Tolstikhina, V.V. Pyrido[2,3-b]indoles (α-carbolines) (review). Chem Heterocycl Compd 20, 345–356 (1984). https://doi.org/10.1007/BF00513842

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00513842

Keywords

Search

Navigation