Synthesis, structural characterization and antioxidative properties of aminopyrazine and imidazolopyrazine derivatives

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Ingrid Devillers, Bertrand de Wergifosse, Marie-Pierre Bruneau, Bernard Tinant, Jean-Paul Declercq, Roland Touillaux, Jean-François Rees and Jacqueline Marchand-Brynaert


Abstract

The reaction of 2-aminopyrazine 1 with the glyoxal derivatives 2a–c gave the bicyclic imidazolopyrazinones 3a,b and the monocyclic N-substituted aminopyrazines 4b and 5c. Compounds 3 feature unique crystallographic characteristics. Their reactivity towards superoxide anion is about five times the reactivity of Trolox®, while the monocyclic pyrazines are inactive.


References

  1. E. M. Thompson and J.-F. Rees, in Biochemistry and Molecular Biology of Fishes, ed. P. W. Hochachka and T. P. Mommsen, Elsevier, 1994, vol. 4, pp. 435–466 Search PubMed.
  2. Y. Ohmiya and T. Hirano, Chem. Biol., 1996, 3, 337 CAS; R. Saito, T. Hirano, H. Niwa and M. Ohashi, J. Chem. Soc., Perkin Trans. 2, 1997, 1711 RSC.
  3. O. Noiset, M. Dubuisson, B. Janssens, B. de Wergifosse, F. Baguet, J. Marchand-Brynaert, A. Trouet and J.-F. Rees, unpublished results.
  4. J.-F. Rees and E. M. Thompson, J. Biolumin. Chemilumin., 1994, 9, 308; J.-F. Rees, B. de Wergifosse, O. Noiset, M. Dubuisson, B. Janssens and E. M. Thompson, J. Exp. Biol., 1998, 201, 1211 Search PubMed.
  5. M. Fontecave and J.-L. Pierre, Bull. Soc. Chim. Fr., 1991, 128, 505.
  6. S. Hollan, Haematologia, 1995, 26, 177 Search PubMed; G. Gille and K. Sigler, Folia Microbiol. (Prague), 1995, 40, 131 Search PubMed; M. H. Gordon, Nat. Prod. Rep., 1996, 265 RSC.
  7. O. Shimomura, B. Musicki and Y. Kishi, Biochem. J., 1989, 261, 913 CAS.
  8. M. Keenan, K. Jones and F. Hibbert, Chem. Commun., 1997, 323 RSC.
  9. T. Goto, M. Isobe, Y. Kishi, S. Inoue and S. Sugiura, Tetrahedron, 1975, 31, 939 CrossRef CAS.
  10. G. B. Barlin, D. J. Brown, Z. Kadune, A. Petric, B. Stanovnik and M. Tisler, Aust. J. Chem., 1983, 36, 1215 CAS.
  11. B. Alcaide, J. Plumet, M. A. Sierra and C. Vicent, J. Org. Chem., 1989, 54, 5763 CrossRef CAS.
  12. T. Hirano, S. Nishibuchi, M. Yoneda, K. Tsujimoto and M. Ohashi, Tetrahedron, 1993, 49, 9267 CrossRef CAS.
  13. T. Goto, S. Inoue and S. Sugiura, Tetrahedron Lett., 1968, 3873 CrossRef CAS.
  14. K. Usami and M. Isobe, Tetrahedron Lett., 1995, 36, 8613 CrossRef CAS.
  15. S. Inoue, H. Kakoi, M. Murata and T. Goto, Tetrahedron Lett., 1977, 2685 CrossRef CAS.
  16. S. Inoue, K. Okada, H. Tanino and H. Kakoi, Chem. Lett., 1987, 417 CAS.
  17. W. D. S. Motherwell and W. Clegg, PLUTO, Program for Plotting Molecular and Crystal Structures, University of Cambridge, 1978.
  18. F. H. Allen, O. Kennard and R. Taylor, Acc. Chem. Res., 1993, 16, 146.
  19. J. C. Calabrese and K. H. Gardner, Acta Crystallogr., Sect. C, 1985, 41, 389 CrossRef.
  20. F. K. Winkler and J. D. Dunitz, Acta Crystallogr., Sect. B, 1975, 31, 278 CrossRef.
  21. K. Miyoshi, J. Wang and T. Mizuta, Inorg. Chim. Acta, 1995, 228, 165 CrossRef CAS.
  22. T. Steiner, Acta Crystallogr., Sect. B, 1998, 54, 456 CrossRef.
  23. K. Teranishi and O. Shimomura, Anal. Biochem., 1997, 249, 37 CrossRef CAS.
  24. K. Akatsu, H. Nakajima, T. Katoh, S. Kino and K. Fujimori, J. Chem. Soc., Perkin Trans. 2, 1995, 1699 RSC.
  25. N. Goto and E. Niki, Methods Enzymol., 1994, 233, 154 CrossRef.
  26. Reference compound prepared from 2-amino-3-benzyl-5-(4-ethoxyphenyl)pyrazine according to Keenan et al.(ref. 8).
  27. G. M. Sheldrick, SHELXS86, in Crystallographic Computing 3, ed. G. M. Sheldrick, C. Kruger and R. Goddard, Oxford, 1985, pp. 175–189 Search PubMed.
  28. G. M. Sheldrick, SHELXL93, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1993.
  29. International Tables for X-Ray Crystallography, The Kynoch Press, Birmingham, 1974, vol. IV Search PubMed.
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