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Synthesis and biological activities of long chain 2-amino alcohols

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Abstract

This article focuses on the synthesis and the biological activities of long chain amino alcohols. The methods for the synthesis of these sphingosine analogues from various starting materials such as lipidic amino acids, serine, glyceraldehydes, long chain 1,2-diols, are summarized in the first part of the review, followed by a discussion of the biological activities of long chain amino alcohols and the applications for the synthesis of other bioactive compounds.

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References

  1. Le Stunff, H., Peterson, C., Liu, H., Milstien, S. and Spiegel, S., Biochim. Biophys. Acta, 1582 (2002) 8.

    Google Scholar 

  2. Cuvillier, O., Pirianov, G., Kleuser B., Vanek, P.G., Coso, O.A., Gutkind, S. and Spiegel, S., Nature, 381 (1996) 800.

    Google Scholar 

  3. Kolesnick, R. and Hannun, Y.A., Trends Biochem. Sci., 24 (1999) 224.

    Google Scholar 

  4. Hannun, Y.A., Science, 274 (1996) 1855.

    Google Scholar 

  5. Kolesnick, R. and Kronke, M., Annu. Rev. Physiol., 60 (1998) 643.

    Google Scholar 

  6. Merrill Jr., A.H. and Hannun, Y.A., Methods Enzymol., 311 (2000) 391.

    Google Scholar 

  7. Koskinen, P.M. and Koskinen, A.M.P., Synthesis, (1998) 1075.

  8. Gibbons, W.A., Hughes, R.A., Charalambous, M., Christodoulou, M., Szeto, A., Aulabough, A.E., Mascagni, P. and Toth, I., Liebigs Ann. Chem., (1990) 1175.

  9. Kokotos, G., Constantinou-Kokotou, V., Noula, C., Nicolaou, A. and Gibbons, W.A., Int. J. Pept. Prot. Res., 48 (1996) 160.

    Google Scholar 

  10. Kokotos, G., Martin, V., Constantinou-Kokotou, V. and Gibbons, W.A., Amino Acids, 11 (1996) 329.

    Google Scholar 

  11. Nicolaou, A., Kokotos, G., Constantinou-Kokotou, V., Charitos, C., Noula, C., Verger, R. and Gibbons, W.A., J. Peptide Sci., 3 (1997) 291.

    Google Scholar 

  12. Toth, I., Danton, M., Flinn, N. and GibbonsW.A., Tetrahedron Lett., 34 (1993) 3925.

    Google Scholar 

  13. Toth, I., J. Drug Targeting, 2 (1994) 217.

    Google Scholar 

  14. Kokotos, G., Padron, J.M., Noula, C., Gibbons, W.A. and Martin, V., Tetrahedron: Aymmetry, 7 (1996) 857.

    Google Scholar 

  15. Kokotos G., Padron, J.M., Martin, T., Gibbons, W.A. and Martin, V., J. Org. Chem., 63 (1998) 3741.

    Google Scholar 

  16. Padron, J.M., Kokotos, G., Martin, T., Markidis, T., Gibbons, W.A. and Martin, V., Tetrahedron: Asymmetry, 9 (1998) 3381.

    Google Scholar 

  17. Markidis, T. and Kokotos, G., J. Org. Chem., 67 (2002) 1685.

    Google Scholar 

  18. Kokotos, G., Constantinou-Kokotou., V., Del Olmo, E., Toth, I. and Gibbons W.A., Liebigs Ann. Chem., (1992) 961.

  19. Kokotos, G. and Noula, C., J. Org. Chem., 61 (1996) 6994.

    Google Scholar 

  20. Kokotos, G., Constantinou-Kokotou, V., Noula, C. and Hadjipavlou-Litina, D., Lipids, 34 (1999) 307.

    Google Scholar 

  21. Girardot, J.M., U.S. Patent (1990) 4,976,733.

  22. Chen, W., Schoen, F.J. and Levy, R.J., Circulation, 90 (1994) 323.

    Google Scholar 

  23. Constantinou-Kokotou, V., Magrioti, V., Markidis, T. and Kokotos, G., J. Peptide Res., 58 (2001) 325.

    Google Scholar 

  24. Magrioti, V. and Constantinou-Kokotou V., Lipids, 37 (2002) 223.

    Google Scholar 

  25. Hirose, R., Hamamichi, N., Kitao Y., Matsuzaki T., Chiba, K. and Fujita, T., Bioorg. Med. Chem. Lett., 6 (1996) 2647.

    Google Scholar 

  26. Magrioti, V., Hadjipavlou-Litina, D. and Constantinou-Kokotou, V., Bioorg. Med. Chem. Lett. 13 (2003) 375.

    Google Scholar 

  27. Kokotos, G., Synthesis, (1990) 299.

  28. Massing, U. and Eibl. H., Chem. Phys. Lipids, 69 (1994) 105.

    Google Scholar 

  29. Sharma, A. and Chattopadhyay S., Tetrahedron: Asymmetry, 10 (1999) 883.

    Google Scholar 

  30. Kokotos, G. and Constantinou-Kokotou, V., J. Chem. Research (S), (1992) 391; J. Chem Research (M), (1992) 3117.

  31. Markidis, T., Padron, J.M., Martin, V., Peters, G.J. and Kokotos, G., Anticancer Res., 21 (2001) 2835.

    Google Scholar 

  32. Karikas, G., Constantinou-Kokotou, V. and Kokotos, G., J. Liq. Chrom. Rel. Technol., 20 (1997) 1789.

    Google Scholar 

  33. Kokotos, G., Theodorou. V., Constantinou-Kokotou, V., Gibbons W.A. and Roussakis, C., Bioorg. Med. Chem. Lett., 8 (1998) 1525.

    Google Scholar 

  34. Del Olmo, E., Macho, A., Alves, M., Lopez, J., El Banoua, F., Munoz, E. and San Feliciano, A., Bioorg. Med. Chem. Lett., 12 (2002) 2621.

    Google Scholar 

  35. Adachi, K., Kohara, T., Nakao, N., Arita, M., Chiba, K., Mishina, T., Sasaki, S. and Fujita, T., Bioorg. Med. Chem. Lett., 5 (1995) 1857.

    Google Scholar 

  36. Bell, R.M., Loomis, C. and Hannun, Y., PCT Int. Appl.WO 88 01,869 (Chem. Abstr. 110 (1989) 88623d).

  37. Padron, J.M., Martin., V., Hadjipavlou-Litina, D., Noula, C., Constantinou-Kokotou, V., Peters, G. and Kokotos, G., Bioorg. Med. Chem. Lett., 9 (1999) 821.

    Google Scholar 

  38. Noula, C., Constantinou-Kokotou, V., Nicolaou, A., Gibbons, W.A. and Kokotos, G., Biochem. Soc. Trans. 24 (1996) 303S.

    Google Scholar 

  39. Lukas, R., Ubeda, A., Paya, M., Alves, M., Del Olmo, E., Lopez, J. and San Feliciano, A., Bioorg. Med. Chem. Lett., 10 (2000) 285.

    Google Scholar 

  40. Del Olmo, E., Alves, M., Lopez, J., Inchaustti, A., Yaluff, G., Rojas de Arias, A. and San Feliciano A., Bioorg. Med. Chem. Lett., 12 (2002) 659.

    Google Scholar 

  41. Chiou, A., Markidis, T., Constantinou-Kokotou, V., Verger, R. and Kokotos, G., Org. Lett., 2 (2000) 347.

    Google Scholar 

  42. Falconer, R., Jablonkai, I. and Toth, I., Tetrahedron Lett., 40 (1999) 8663.

    Google Scholar 

  43. Falconer, R. and Toth. I., In Martinez, J. and Fehrentz J.-A. (eds), 'Peptides 2000', Proceedings of the European Peptide Symposium, Monpellier, 2000, EDK, Paris, France 2001, pp. 307.

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Constantinou-Kokotou, V. Synthesis and biological activities of long chain 2-amino alcohols. Letters in Peptide Science 9, 143–152 (2002). https://doi.org/10.1023/A:1024190024487

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