Advertisement

Russian Chemical Bulletin

, Volume 60, Issue 5, pp 873–881 | Cite as

Synthesis of the (2S,4S)-stereoisomers of 4-(indol-1-yl) and 4-arylamino derivatives of 5-oxoproline, proline, and 2-hydroxymethylpyrrolidine

  • A. Yu. Vigorov
  • I. A. Nizova
  • K. E. Shalunova
  • A. N. Grishakov
  • L. Sh. Sadretdinova
  • I. N. Ganebnykh
  • M. A. Ezhikova
  • M. I. Kodess
  • V. P. Krasnov
Full Articles

Abstract

Nucleophilic substitution of the halogen atom in dimethyl (S)-4-bromoglutamate followed by removal of the protecting groups and closure of a lactam ring afforded (2S,4S)-4-(indolin-1-yl)-5-oxoproline. The indoline fragment was oxidized into the indole fragment to give (2S,4S)-4-(indol-1-yl)-5-oxoproline; reduction of the carbonyl groups with BH3 yielded (2S,4S)-4-(indol-1-yl)prolines and (2S,4S)-2-hydroxymethyl-4-(indol-1-yl)pyrrolidines. Reduction of (2S,4S)-4-arylamino-5-oxoprolines with BH3 to the corresponding (2S,4S)-4-arylaminoprolines and (2S,4S)-4-arylamino-2-hydroxymethylpyrrolidines was studied.

Key words

4-aminoproline glutamic acid indole 5-oxoproline proline prolinol 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    H.-D. Jakubke, H. Jeschkeit, Aminosäuren, Peptide, Proteine, Eine Einführung, Akademie Verlag, Berlin, 1982, 505 S.Google Scholar
  2. 2.
    C. Nájera, M. Yus, Tetrahedron: Asymmetry, 1999, 10, 2245.CrossRefGoogle Scholar
  3. 3.
    S. K. Panday, J. Prasad, D. K. Dikshit, Tetrahedron: Asymmetry, 2009, 20, 1581.CrossRefGoogle Scholar
  4. 4.
    C. E. Schafmeister, Z. Z. Brown, S. Gupta, Acc. Chem. Res., 2008, 41, 1387.CrossRefGoogle Scholar
  5. 5.
    R. B. Silverman, Acc. Chem. Res., 2009, 42, 439.CrossRefGoogle Scholar
  6. 6.
    T. E. Kristensen, T. Hansen, Eur. J. Org. Chem., 2010, 3179.Google Scholar
  7. 7.
    S. G. Zlotin, A. S. Kucherenko, I. P. Beletskaya, Usp. Khim., 2009, 78, 796 [Russ. Chem. Rev. (Engl. Transl.), 2009, 78, 737].Google Scholar
  8. 8.
    A. ErkkilChem. Rev., 2007, 107, 5416.Google Scholar
  9. 9.
    S. P. Gupta, D. Kumar, S. Kumaran, Bioorg. Med. Chem., 2003, 11, 1975.CrossRefGoogle Scholar
  10. 10.
    H. Sakashita, F. Akahoshi, H. Kitajima, R. Tsutsumiuchi, Y. Hayashi, Bioorg. Med. Chem., 2006, 14, 3662.CrossRefGoogle Scholar
  11. 11.
    D. Torino, A. Mollica, F. Pinnen, F. Feliciani, S. Spisani, G. Lucente, Bioorg. Med. Chem., 2009, 17, 251.CrossRefGoogle Scholar
  12. 12.
    S. Flemer, A. Wurthmann, A. Mamai, J. S. Madalengoitia, J. Org. Chem., 2008, 73, 7593.CrossRefGoogle Scholar
  13. 13.
    A. Flores-Ortega, J. Casanovas, X. Assfeld, C. Aleman, J. Org. Chem., 2009, 74, 3101.CrossRefGoogle Scholar
  14. 14.
    A. Evidente, A. Andolfi, M. Vurro, M. C. Zonno, A. Motta, Phytochemistry, 2000, 53, 231.CrossRefGoogle Scholar
  15. 15.
    D. D. Schoepp, B. G. Johnson, C. R. Salhoff, M. J. Valli, M. A. Desai, J. P. Burnett, N. G. Mayne, J. A. Monn, Neuropharmacology, 1995, 34, 843.CrossRefGoogle Scholar
  16. 16.
    M. G. Moloney, Nat. Prod. Rep., 2002, 19, 597.CrossRefGoogle Scholar
  17. 17.
    V. Bruno, G. Battaglia, A. Copani, M. D’Onofrio, P. Di Iorio, A. De Blasi, D. Melchiorri, P. J. Flor, F. Nicoletti, J. Cereb. Blood Flow Metab., 2001, 21, 1013.CrossRefGoogle Scholar
  18. 18.
    S. Süzen, Top. Heterocycl. Chem., 2007, 11, 145.CrossRefGoogle Scholar
  19. 19.
    M. N. Preobrazhenskaya, A. M. Korolev, Bioorg. Khim., 2000, 26, 97 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2000, 26, 85].Google Scholar
  20. 20.
    G. Laconde, P. Carato, J. H. Poupaert, P. Berthelot, P. Depreux, J.-P. Hénichart, Monatsh. Chem., 2003, 134, 1037 (and references cited therein).CrossRefGoogle Scholar
  21. 21.
    V. P. Krasnov, I. M. Bukrina, E. A. Zhdanova, M. I. Kodess, M. A. Korolyova, Synthesis, 1994, 961.Google Scholar
  22. 22.
    V. P. Krasnov, A. Yu. Vigorov, I. A. Nizova, T. V. Matveeva, A. N. Grishakov, I. V. Bazhov, A. A. Tumashov, M. A. Ezhikova, M. I. Kodess, Eur. J. Org. Chem., 2007, 4257.Google Scholar
  23. 23.
    V. P. Krasnov, A. Yu. Vigorov, I. A. Nizova, A. N. Grishakov, N. G. Evstigneeva, M. I. Kodess, Izv. Akad. Nauk, Ser. Khim., 2004, 1274 [Russ. Chem. Bull., Int. Ed., 2004, 53, 1327].Google Scholar
  24. 24.
    I. A. Nizova, V. P. Krasnov, O. V. Korotovskikh, L. V. Alekseeva, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 2781 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1989, 38, 2545].Google Scholar
  25. 25.
    M. N. Preobrazhenskaya, Usp. Khim., 1967, 36, 1760 [Russ. Chem. Rev. (Engl. Transl.), 1967, 36, 753].Google Scholar
  26. 26.
    C. J. Salomon, E. G. Mata, O. A. Mascaretti, J. Org. Chem., 1994, 59, 7259.CrossRefGoogle Scholar
  27. 27.
    F. Lenda, F. Guenoun, J. Martinez, F. Lamaty, Tetrahedron Lett., 2007, 48, 805.CrossRefGoogle Scholar
  28. 28.
    D. K. Dikshit, S. K. Panday, J. Org. Chem., 1992, 57, 1920.CrossRefGoogle Scholar
  29. 29.
    V. P. Krasnov, I. A. Nizova, A. Yu. Vigorov, T. V. Matveeva, G. L. Levit, P. A. Slepukhin, M. A. Ezhikova, M. I. Kodess, Eur. J. Org. Chem., 2008, 1802.Google Scholar
  30. 30.
    J. Ezquerra, C. Pedregal, A. Rubio, B. Yruretagoyena, A. Escribano, F. Sanchez-Ferrando, Tetrahedron, 1993, 49, 8665.CrossRefGoogle Scholar
  31. 31.
    E. A. Elin, V. V. Onoprienko, I. A. Kudelina, A. I. Miroshnikov, Bioorg. Khim., 2000, 26, 862 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2000, 26, 774].Google Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • A. Yu. Vigorov
    • 1
  • I. A. Nizova
    • 1
  • K. E. Shalunova
    • 1
  • A. N. Grishakov
    • 1
  • L. Sh. Sadretdinova
    • 1
  • I. N. Ganebnykh
    • 1
  • M. A. Ezhikova
    • 1
  • M. I. Kodess
    • 1
  • V. P. Krasnov
    • 1
  1. 1.I. Ya. Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesEkaterinburgRussian Federation

Personalised recommendations