Skip to main content
SpringerLink
Log in

Marine indole alkaloids containing an 1-(indol-3-yl)ethane-1,2-diamine fragment (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Data on the isolation from natural sources, biological properties, and synthesis of indole alkaloids containing an 1-(indol-3-yl)ethane-1,2-diamine fragment are reviewed.

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

References

  1. A. E. Wright, in: S. K. Wrigley, M. A. Hayes, R. Thomas, E. J. T. Chrystal, and N. Nicholson (editors), Biodiversity: New Leads for the Pharmaceutical and Agrochemical Industries, Royal Society of Chemistry, Cambridge (2000), p. 113.

  2. D. J. Newman, G. M. Cragg, and K. M. Snader, J. Nat. Prod., 66, 1022 (2003).

    Article  CAS  Google Scholar 

  3. G. M. Cragg, P. G. Grothaus, and D. J. Newman, Chem. Rev., 109, 3012 (2009).

    Article  CAS  Google Scholar 

  4. M. Hesse, Alkaloids: Nature's Curse or Blessing, Wiley-VCH, Weinheim (2002), p. 14.

  5. M. Ishikura and K. Yamada, Nat. Prod. Rep., 26, 803 (2009).

    Article  CAS  Google Scholar 

  6. T. Kawasaki and K. Higuchi, Nat. Prod. Rep., 24, 843 (2007).

    Article  Google Scholar 

  7. M. Somei and F. Yamada, Nat. Prod. Rep., 22, 73 (2005).

    Article  CAS  Google Scholar 

  8. K. Higuchi and T. Kawasaki, Nat. Prod. Rep., 22, 761 (2005).

    Article  Google Scholar 

  9. M. Somei and F. Yamada, Nat. Prod. Rep., 21, 278 (2004).

    Article  CAS  Google Scholar 

  10. M. Somei and F. Yamada, Nat. Prod. Rep., 20, 216 (2003).

    Article  CAS  Google Scholar 

  11. S. Hibino and T. Choshi, Nat. Prod. Rep., 19, 148 (2002).

    Article  CAS  Google Scholar 

  12. D. Skropeta, Nat. Prod. Rep., 25, 1131 (2008).

    Article  CAS  Google Scholar 

  13. С.-G. Yang, H. Huang, and B. Jiang, Curr. Org. Chem., 8, 1691 (2004).

    Article  CAS  Google Scholar 

  14. J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote, and M. R. Prinsep, Nat. Prod. Rep., 23, 26 (2006).

    Article  CAS  Google Scholar 

  15. A. Mollica, M. Locatelli, A. Stefanucci, and F. Pinnen, Molecules, 17, 6083 (2012).

    Article  CAS  Google Scholar 

  16. W. Gul and M. T. Hamann, Life Sci., 78, 442 (2005).

    Article  CAS  Google Scholar 

  17. S. Sagar, M. Kaur, and K. P. Minneman, Mar. Drugs, 8, 2619 (2010).

    Article  CAS  Google Scholar 

  18. H. H. Sun and S. Sakemi, J. Org. Chem., 56, 4307 (1991).

    Article  CAS  Google Scholar 

  19. J. Cohen, G. K. Paul, S. P. Gunasekera, R. E. Longley, and S. A. Pomponi, Pharm. Biol., 42, 59 (2004).

    Article  CAS  Google Scholar 

  20. R. J. Capon, C. Peng, and C. Dooms, Org. Biomol. Chem., 6, 2765 (2008).

    Article  CAS  Google Scholar 

  21. K. Bartik, J.-C. Braekman, D. Daloze, C. Stoller, J. Huysecom, G. Vandevyver, and R. Ottinger, Can. J. Chem., 65, 2118 (1987).

    Article  CAS  Google Scholar 

  22. S. Tsujii, K. L. Rinehart, S. P. Gunasekera, Y. Kashman, S. S. Cross, M. S. Lui, S. A. Pomponi, and M. C. Diaz, J. Org. Chem., 53, 5446 (1988).

    Article  CAS  Google Scholar 

  23. S. A. Morris and R. J. Andersen, Can. J. Chem., 67, 677 (1989).

    Article  CAS  Google Scholar 

  24. J. C. Braekman, D. Daloze, B. Moussiaux, C. Stoller, and F. Deneubourg, Pure Appl. Chem., 61, 509 (1989).

    Article  CAS  Google Scholar 

  25. S. A. Morris and R. J. Andersen, Tetrahedron, 46, 715 (1990).

    Article  CAS  Google Scholar 

  26. S. Sakemi and H. H. Sun, J. Org. Chem., 56, 4304 (1991).

    Article  CAS  Google Scholar 

  27. L. M. Murray, T. K. Lim, J. N. A. Hooper, and R. J. Capon, Aust. J. Chem., 48, 2053 (1995).

    Article  CAS  Google Scholar 

  28. J. Shin, Y. Seo, K. W. Cho, J.-R. Rho, and C. J. Sim, J. Nat. Prod., 62, 647 (1999).

    Article  CAS  Google Scholar 

  29. A. Casapullo, G. Bifulco, I. Bruno, and R. Riccio, J. Nat. Prod., 63, 447 (2000).

    Article  CAS  Google Scholar 

  30. B. Bao, Q. Sun, X. Yao, J. Hong, C.-O. Lee, C. J. Sim, K. S. Im, and J. H. Jung, J. Nat. Prod., 68, 711 (2005).

    Article  CAS  Google Scholar 

  31. K.-B. Oh, W. Mar, S. Kim, J.-Y. Kim, M.-N. Oh, J.-G. Kim, D. Shin, C. J. Sim, and J. Shin, Bioorg. Med. Chem. Lett., 15, 4927 (2005).

    Article  CAS  Google Scholar 

  32. J. H. Jung, P. B. Shinde, J. Hong, Y. Liu, and C. J. Sim, Biochem. Syst. Ecol., 35, 48 (2007).

    Article  CAS  Google Scholar 

  33. B. Bao, Q. Sun, X. Yao, J. Hong, C.-O. Lee, H. Y. Cho, and J. H. Jung, J. Nat. Prod., 70, 2 (2007).

    Article  CAS  Google Scholar 

  34. S. P. Gunasekera, S. S. Cross, Y. Kashman, M. S. Lui, K. L. Rinehart, and S. Tsujii, US Pat. Appl. 4866084.

  35. K.-B. Oh, W. Mar, S. Kim, J.-Y. Kim, T.-H. Lee, J.-G. Kim, D. Shin, C. J. Sim, and J. Shin, Biol. Pharm. Bull., 29, 570 (2006).

    Article  CAS  Google Scholar 

  36. O. J. McConnell, G. Saucy, and R. Jacobs, US Pat. Appl. 5290777.

  37. R. Zoraghi, L. Worrall, R. H. See, W. Strangman, W. L. Popplewell, H. Gong, T. Samaai, R. D. Swayze, S. Kaur, M. Vuckovic, B. B. Finlay, R. C. Brunham, W. R. McMaster, M. T. Davies-Coleman, N. C. Strynadka, R. J. Andersen, and N. E. Reiner, J. Biol. Chem., 286, 44716 (2011).

    Article  CAS  Google Scholar 

  38. J. C. Braekman, D. Daloze, B. Mouissiaux, C. Stoller, and F. Deneubourg, Bull. Soc. Chim. Belg., 96, 809 (1987).

    Article  CAS  Google Scholar 

  39. F. Y. Miyake, K. Yakushijin, and D. A. Horne, Org. Lett., 2, 2121 (2000).

    Article  CAS  Google Scholar 

  40. S. Achab, Tetrahedron Lett., 37, 5503 (1996).

    Article  CAS  Google Scholar 

  41. S. K. Mal, L. Bohé, and S. Achab, Tetrahedron, 64, 5904 (2008).

    Article  CAS  Google Scholar 

  42. I. Kawasaki, H. Katsuma, Y. Nakayama, M. Yamashita, and S. Ohta, Heterocycles, 48, 1887 (1998).

    Article  CAS  Google Scholar 

  43. X. Guinchard, Y. Vallée, and J.-N. Denis, J. Org. Chem., 72, 3972 (2007).

    Article  CAS  Google Scholar 

  44. X. Guinchard, Y. Vallée, and J.-N. Denis, Org. Lett., 9, 3761 (2007).

    Article  CAS  Google Scholar 

  45. H. Chalaye-Mauger, J.-N. Denis, M.-T. Averbuch-Pouchot, and Y. Vallée, Tetrahedron, 56, 791 (2000).

    Article  CAS  Google Scholar 

  46. J.-N. M. L. Denis, X. J. G. M. Guinchard, N. L. N. J. Laffont, and Y. Vallee, US Pat. Appl. 20100144726.

  47. X. Guinchard and J.-N. Denis, J. Org. Chem., 73, 2028 (2008).

    Article  CAS  Google Scholar 

  48. K. Murai, M. Morishita, R. Nakatani, O. Kubo, H. Fujioka, and Y. Kita, J. Org. Chem., 27, 8947 (2007).

    Article  Google Scholar 

  49. E. N. Jacobsen, I. Markó, W. S. Mungall, G. Schröder, and K. B. Sharpless, J. Am. Chem. Soc., 110, 1968 (1988).

    Article  CAS  Google Scholar 

  50. H. H. Sun, S. Sakemi, S. Gunasekera, Y. Kashman, M. Lui, N. Burres, and P. McCarthy, US Pat. Appl. 4970226.

  51. I. Mancini, G. Guella, C. Debitus, J. Waikedre, and F. Pietra, Helv. Chim. Acta, 79, 2075 (1996).

    Article  CAS  Google Scholar 

  52. I. Kawasaki, M. Yamashita, and S. Ohta, J. Chem. Soc., Chem. Commun., 2085 (1994).

  53. I. Kawasaki, M. Yamashita, and S. Ohta, Chem. Pharm. Bull., 44, 1831 (1996).

    Article  Google Scholar 

  54. C. J. Moody and J. R. A. Roffey, ARKIVOC, iii, 393 (2000).

  55. S. Kohmoto, Y. Kashman, O. J. McConnell, K. L. Rinehart, Jr., A. Wright, and F. Koehn, J. Org. Chem., 53, 3116 (1988).

    Article  CAS  Google Scholar 

  56. T. Kawasaki, K. Ohno, H. Enoki, Y. Umemoto, and M. Sakamoto, Tetrahedron Lett., 43, 4245 (2002).

    Article  CAS  Google Scholar 

  57. E. Fahy, B. C. M. Potts, D. J. Faulkner, and K. Smith, J. Nat. Prod., 54, 564 (1991).

    Article  CAS  Google Scholar 

  58. A. E. Wright, S. A. Pomponi, S. S. Cross, and P. McCarthy, J. Org. Chem., 57, 4772 (1992).

    Article  CAS  Google Scholar 

  59. R. J. Capon, F. Rooney, L. M. Murray, E. Collins, A. T. R. Sim, J. A. P. Rostas, M. S. Butler, and A. R. Carroll, J. Nat. Prod., 61, 660 (1998).

    Article  CAS  Google Scholar 

  60. A. Cutignano, G. Bifulco, I. Bruno, A. Casapullo, L. Gomez-Paloma, and R. Riccio, Tetrahedron, 56, 3743 (2000).

    Article  CAS  Google Scholar 

  61. N. K. Garg, R. Sarpong, and B. M. Stoltz, J. Am. Chem. Soc., 124, 13179 (2002).

    Article  CAS  Google Scholar 

  62. D. Mandal, A. D. Yamaguchi, J. Yamaguchi, and K. Itami, J. Am. Chem. Soc., 133, 19660 (2011).

    Article  CAS  Google Scholar 

  63. K. S. Feldman and P. Ngernmeesri, Synlett, 1882 (2012).

  64. K. S. Feldman and P. Ngernmeesri, Org. Lett., 13, 5704 (2011)

    Article  CAS  Google Scholar 

  65. N. K. Garg, D. D. Caspi, and B. M. Stoltz, J. Am. Chem. Soc., 126, 9552 (2004).

    Article  CAS  Google Scholar 

  66. N. K. Garg, D. D. Caspi, and B. M. Stoltz, J. Am. Chem. Soc., 127, 5970 (2005).

    Article  CAS  Google Scholar 

  67. B. Jiang, J. M. Smallheer, C. Amaral-Ly, and M. A. Wuonola, J. Org. Chem., 59, 6823 (1994).

    Article  CAS  Google Scholar 

  68. T. Kawasaki, H. Enoki, K. Matsumura, M. Ohyama, M. Inagawa, and M. Sakamoto, Org. Lett., 2, 3027 (2000).

    Article  CAS  Google Scholar 

  69. C. R. Whitlock and M. P. Cava, Tetrahedron Lett., 35, 371 (1994).

    Article  CAS  Google Scholar 

  70. F. Y. Miyake, K. Yakushijin, and D. A. Horne, Org. Lett., 2, 3185 (2000).

    Article  CAS  Google Scholar 

  71. F. Tonsiengsom, F. Y. Miyake, K. Yakushijin, and D. A. Horne, Synthesis, 49 (2006).

  72. N. K. Garg and B. M. Stoltz, Tetrahedron Lett., 46, 2423 (2005).

    Article  CAS  Google Scholar 

  73. C.-G. Yang, J. Wang, X.-X. Tang, and B. Jiang, Tetrahedron: Asymmetry, 13, 383 (2002).

    Article  CAS  Google Scholar 

  74. K. L. Reddy and K. B. Sharpless, J. Am. Chem. Soc., 120, 1207 (1998).

    Article  CAS  Google Scholar 

  75. M. Anstiss and A. Nelson, Org. Biomol. Chem., 4, 4135 (2006).

    Article  CAS  Google Scholar 

  76. S. P. Gunasekera, P. J. McCarthy, and M. Kelly-Borges, J. Nat. Prod., 57, 1437 (1994).

    Article  CAS  Google Scholar 

  77. B. Jiang, C.-G. Yang, and J. Wang, J. Org. Chem., 66, 4865 (2001).

    Article  CAS  Google Scholar 

  78. B. Jiang, C.-G. Yang, and J. Wang, J. Org. Chem., 67, 1396 (2002).

    Article  CAS  Google Scholar 

  79. T. Kouko, K. Matsumura, and T. Kawasaki, Tetrahedron, 61, 2309 (2005).

    Article  CAS  Google Scholar 

  80. F. Y. Miyake, K. Yakushijin, and D. A. Horne, Org. Lett., 4, 941 (2002).

    Article  CAS  Google Scholar 

  81. T. Kawasaki, T. Kouko, H. Totsuka, and K. Hiramatsu, Tetrahedron Lett., 44, 8849 (2003).

    Article  CAS  Google Scholar 

  82. K. Higuchi, R. Takei, T. Kouko, and T. Kawasaki, Synthesis, 669 (2007).

Download references

Author information

Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, Leninskie Gory, 1, Bld. 3, Moscow, 119991, Russia

    N. E. Golantsov, A. V. Karchava & M. A. Yurovskaya

  2. Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    A. A. Festa

Authors
  1. N. E. Golantsov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. A. Festa
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Karchava
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. A. Yurovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. E. Golantsov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 224-248, February, 2013.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Golantsov, N.E., Festa, A.A., Karchava, A.V. et al. Marine indole alkaloids containing an 1-(indol-3-yl)ethane-1,2-diamine fragment (Review). Chem Heterocycl Comp 49, 203–225 (2013). https://doi.org/10.1007/s10593-013-1238-9

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-013-1238-9

Keywords

Search

Navigation