Design, synthesis and antioxidant properties of ovothiol-derived 4-mercaptoimidazoles

(Note: The full text of this document is currently only available in the PDF Version )

Vincent Zoete, Fabrice Bailly, Jean-Pierre Catteau and Jean-Luc Bernier


Abstract

Fourteen 4-mercaptoimidazoles derived from the naturally occurring family of antioxidants, the ovothiols, have been synthesized by cyclization of thioamides with trimethylsilyl trifluoromethanesulfonate (triflate). These compounds have been assayed for their radical-scavenging activity.


References

  1. H. Sies, Angew. Chem., Int. Ed. Engl., 1986, 25, 1058 CrossRef.
  2. C. A. Rice-Evans and A. T. Diplock, Free Rad. Biol. Med., 1993, 15, 77 CrossRef.
  3. B. Halliwell and J. M. C. Gutteridge, in Free radicals in biology and medicine, Oxford University Press, Oxford, 1989 Search PubMed.
  4. M. Fontecave and J. L. Pierre, Bull. Soc. Chim. Fr., 1991, 128, 505.
  5. R. H. Schirmer, J. G. Müller and R. L. Krauth-Siegel, Agnew. Chem., Int. Ed. Engl., 1995, 34, 141 Search PubMed.
  6. R. Schreck, K. Albermann and P. A. Baeuerle, Free Rad. Res. Commun., 1992, 17, 221 Search PubMed.
  7. M. B. Toledano and W. J. Leonard, Proc. Natl. Acad. Sci. USA, 1991, 88, 4328 CAS.
  8. F. Müller, Free Rad. Biol. Med., 1992, 13, 651 CrossRef CAS.
  9. M. Roederer, S. W. Ela, F. J. Staal and L. A. Herzenberg, AIDS Res. Hum. Retrovir., 1992, 8, 209 Search PubMed.
  10. Y. J. Suzuki and L. Packer, Biochem. Biophys. Res. Commun., 1993, 193, 277 CrossRef CAS.
  11. N. I. Krinsky, Free Rad. Biol. Med., 1993, 7, 617 CrossRef CAS.
  12. R. A. Axford-Gutley and G. J. Wilson, Cardiovasc. Res, 1991, 25, 89.
  13. B. Hennig, C. Enoch and C. K. Chew, Nutr. Res., 1987, 7, 1242.
  14. S. Partharanthy, S. G. Young, J. L. Witzum, R. G. Pittman and D. Steinberg, J. Clin. Invest., 1986, 7, 641 Search PubMed.
  15. S. V. Jovanovic, S. Steeken, M. Tosic, B. Marjanovic and M. G. Simic, J. Am. Chem. Soc., 1994, 116, 4846 CrossRef CAS.
  16. N. Cotelle, J. L. Bernier, J. P. Hénichart, J. P. Catteau, E. Gaydou and J. C. Wallet, Free Rad. Biol. Med., 1992, 13, 211 CrossRef CAS.
  17. P. M. Mehta, K. Przyklenk and R. A. Kloner, Eur. Heart J., 1990, 11, 94 CAS.
  18. I. A. Cotgreave and P. Moldeus, Bull. Eur. Physiopathol. Respir., 1987, 23, 275 Search PubMed.
  19. B. Amor, C. Mercy and A. Degery, Arthritis, 1982, 25, 698 Search PubMed.
  20. E. Turner, R. Klevit, L. J. Hager and B. M. Shapiro, Biochemistry, 1987, 26, 4028 CrossRef CAS.
  21. E. Turner, L. J. Hager and B. M. Shapiro, Science, 1988, 252, 939.
  22. B. M. Shapiro, Science, 1991, 252, 533 CAS.
  23. J. W. Heinecke and B. M. Shapiro, J. Biol. Chem., 1992, 267, 7959 CAS.
  24. K. H. Weaver and D. L. Rabenstein, J. Org. Chem., 1995, 60, 1904 CrossRef CAS.
  25. T. P. Holler and P. B. Hopkins, J. Am. Chem. Soc., 1988, 110, 4837 CrossRef CAS.
  26. T. P. Holler and P. B. Hopkins, Biochemistry, 1990, 29, 1953 CrossRef CAS.
  27. H. G. Viehe, R. Merenyi, L. Stella and Z. Janousek, Angew. Chem., Int. Ed. Engl., 1979, 18, 917 CrossRef.
  28. H. G. Viehe, Z. Janousek, R. Merenyi and L. Stella, Acc. Chem. Res., 1985, 18, 148 CrossRef CAS.
  29. C. Bienarz and M. J. Cornwell, Tetrahedron Lett., 1993, 34, 939 CrossRef.
  30. F. Asinger, A. Sans, H. Offermanns, P. Krings and H. Andree, Justus Liebigs Ann. Chem., 1971, 744, 51 CAS.
  31. F. Asinger, A. Sans and H. D. Hahn, Justus Liebigs Ann. Chem., 1966, 691, 92 CAS.
  32. J. C. Caille, S. Didierlaurent, D. Lefrançois, M. H. Lelièvre, C. Sury and J. Aszodi, Synthesis, 1995, 6, 635 CrossRef.
  33. A. Spaltenstein, T. P. Holler and P. B. Hopkins, J. Org. Chem., 1987, 52, 2977 CrossRef CAS.
  34. V. S. Zyabrev, V. V. Kiselev, E. O. Romanenko and B. S. Drach, Zh. Org. Khim., 1994, 5, 715.
  35. H. Zimmer, D. C. Lankin and S. W. Morgan, Chem. Rev., 1971, 71, 229 CrossRef CAS.
  36. M. S. Blois, Nature, 1958, 181, 1199 CAS.
  37. H. J. Ha, G. S. Nam and K. P. Park, Synth. Commun., 1991, 21, 155 CAS.
  38. K. Takahashi, T. Masuda, K. Ogura and H. Iida, Synthesis, 1983, 12, 1043 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.