Synthesis of New 5-Nitroimidazoles Highly Active Against Anaerobes by Substitution Reactions which Proceed via Radical and Radical-Anion Intermediates

  • M.P. Crozet
  • O. Jentzer
  • P. Vanelle
Part of the NATO ASI Series book series (ASIC, volume 260)


Electron-transfer substitution reactions which proceed via radical and radical-anion intermediates (SRN1) were extended to heterocyclic electrophiles of the nitroimiaazole series and to heterocyclic nucleophiles prepared from 3-nitrolactams. New 5-nitroimidazoles bearing a trisubstituted ethylenic double bond in position 2 were obtained in good yields. Biological assays have shown that several of these compounds are highly active against anaerobes in vivo. The best compound was found to be greater than 40-fold more active than metronidazole (Flagyl*).


Nitro Group Clostridium Perfringens Ames Test Lithium Salt Butylli Thium 
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  1. 1-.
    Cosar, N.; Crisan, C.; Horclois, R.; Jacob, R.N.; Robert, J.; Tchelitcheff, S.; Vaupré, R. Arzneim-Forsch. 1966, 16, 23.Google Scholar
  2. 2-.
    Shinn, D.L.S. Lancet, 1962, 1, 1191.CrossRefGoogle Scholar
  3. 3-.
    Nitroimidazoles: Chemistry, Pharmacology and Clinical Applications, Breccia, A.; Cavalleri, B.; Adams, G.E., Ed. Plenum Press, New York, 19832, Vol.42.Google Scholar
  4. 4-.
    Edwards, D.I.; “Modes and Mechanisms of Microbial Growth Inhibitors“ in Antibiotics, Hahn, F.E.; Ed.; Springer-Verlag, Berlin, 1983, Vol. VI, pp. 121–135.Google Scholar
  5. 5-.
    Nair, M.D.; Nagarajan, K. “Nitroimidazoles as Chemiotherapeutic Agents” in Progress in Drug Research, Jucker, E.; Ed.; Birkhauser Verlag, Basel, 1983, Vol. 27, pp. 163–252.Google Scholar
  6. 6(a)-.
    Kornblum, N.; Michel, R.E.; Kerber, R.C. J. Am. Chem. Soc. 1966, 88, 5660 and and 5662.CrossRefGoogle Scholar
  7. 6(b)-.
    Russell, G.A.; Danen, W.C. J. Am. Chem. Soc. 1966, 88, 5663.CrossRefGoogle Scholar
  8. 7-.
    Bunnett, J.F.; Kim, J.K. J. Am. Chem. Soc, 1970, 92, 7463.CrossRefGoogle Scholar
  9. 8(a)-.
    Crozet, M.P.; Surzur, J.M.; Vanelle, P.; Ghiglione, C.; Maldonado, J. Tetrahedron Lett. 1985, 26, 1023.CrossRefGoogle Scholar
  10. 8(b)-.
    Crozet, M.P.; Archaimbault, G.; Vanelle, P.; Nouguier, R. Tetrahedron Lett. 1985, 26, 5133.CrossRefGoogle Scholar
  11. 8(c)-.
    Crozet, M.P.; Vanelle, P.; Jentzer, O.; Maldonado, J. C.R. Acad. Sci., Ser. II, 1988, 306, 967.Google Scholar
  12. 9-.
    Feuer, H. “Alkyl nitrate nitrations” in The Chemistry of amino, nitroso and nitro compounds and their derivatives, Supplement F, Part 2, Patai, S.; Ed., Wiley, New York, 1982, Chap. 19, pp. 805–847.CrossRefGoogle Scholar
  13. 10-.
    Feuer, H.; Panda, C.S.; Hou, L.; Bevinakatti, H.S. Synthesis, 1983, 187.Google Scholar
  14. 11-.
    Walsh, J.S.; Wang, R.; Bagan, E.; Wang, C.C.; Wislacki, P.; Miwa, G.T. J. Med. Chem, 1987, 30, 150.CrossRefGoogle Scholar

Copyright information

© Kluwer Academic Publishers 1989

Authors and Affiliations

  • M.P. Crozet
    • 1
  • O. Jentzer
    • 1
  • P. Vanelle
    • 1
  1. 1.CNRS UA 10°Aix-Marseille UniversityMarseille Cedex 13France

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