Advertisement

Nitroimidazole Chemistry I: Synthetic Methods

  • Bruno Cavalleri
Part of the NATO Advanced Study Institutes Series book series (NSSA, volume 42)

Abstract

The first report (1) on the antitrichomonas activity of Azomycin* (I), obtained from fermentation of a strain of Nocardia mesenterica (2,3), appeared in 1956, and the first publications on synthetics (4) dealt with some transformations of natural 2-nitro-imidazole.

Keywords

Nitro Group Sodium Nitrite Cerium Ammonium Nitrate Cerium Ammonium Imine Nitrogen 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    H. Horie, J. Antibiotics Ser. A. 9: 168 (1956).Google Scholar
  2. 2.
    S. Nakamura, Pharm. Bull. 3: 379 (1955).PubMedGoogle Scholar
  3. 3.
    K. Maeda, T. Osato, and H. Umezawa, J. Antibiotics, Ser. A. 6: 182 (1953).Google Scholar
  4. 4.
    G. C. Lancini, N. Maggi, and P. Sensi, II. Farmaco, Ed. Sci. 18:390 (1963).Google Scholar
  5. 5.
    F. Rung, and M. Behrend, Ann. 271: 28 (1892).Google Scholar
  6. 6.
    A. Windaus, Ber. 42: 758 (1909).Google Scholar
  7. 7.
    R. M. Jacob, G. L. Régnier, and C. Crisan, U.S. Patent 2, 944, 061, July 1960 - Chem. Abstr. 55:1657 (1961).Google Scholar
  8. 8.
    C. Cosar, C. Crisan, R. Horclois, R. M. Jacob, S. Tchelitcheff, and R. Vaupré, Arzneim-Forsch.(Drug. Res.), 16: 23 (1966).Google Scholar
  9. 9.
    K.C. Agrawal, K.B. Bears, and R. K. Sehgal, J. Med. Chem. 22: 583 (1979).PubMedCrossRefGoogle Scholar
  10. 10.
    R. K. Sehgal, and K. C. Agrawal, J. Heterocycl. Chem. 16: 1499 (1979).CrossRefGoogle Scholar
  11. 11.
    J. Suwinski, E. Salwinska, J. Watras, and M. Widel, Abstracts of the “Int. Conference on the Chemistry, Pharmacology and Clinical Application of Nitroimidazoles”, Cesenatico (Italy) August 1980, page 46.Google Scholar
  12. 12.
    K. Hofmann, “Imidazole and Its Derivatives”, Part I, in: “The Chemistry of Heterocyclic Compounds”, Interscience Publishers Inc., New York (1953).Google Scholar
  13. 13.
    G. C. Lancini, D. Kluepfel, E. Lazzari, and G. Sartori, Biochim. Biophys. Acta, 130: 37 (1966).CrossRefGoogle Scholar
  14. 14.
    Y. Seki, T. Nakamura, and Y. Okami, Biochem. J. 67: 389 (1970).Google Scholar
  15. 15.
    G. C. Lancini, E. Lazzari, and G. Sartori, J. Antibiotics 6: 387 (1968).CrossRefGoogle Scholar
  16. 16.
    A. F. Pozharskii, E. A. Zvezdina, and A. M. Simonov, Tetrahedron Letters, 23: 2219 (1967).PubMedCrossRefGoogle Scholar
  17. 17.
    M. D. Coburn, J. Heterocycl. Chem. 7: 455 (1970).CrossRefGoogle Scholar
  18. 18.
    G. C. Lancini, and E. Lazzari, Experientia 21: 1 (1965).CrossRefGoogle Scholar
  19. 19.
    A. G. Beaman, W. Tautz, T. Gabriel, and R. Duschinsky, J. Am. Chem. Soc. 87: 389 (1965).PubMedCrossRefGoogle Scholar
  20. 20.
    A. G. Beaman, W. Tautz, T. Gabriel, 0. Keller, V. Toome, and T. Duschinsky, Antim. Agents Chemother. 1965: 469Google Scholar
  21. 21.
    G. C. Lancini, E. Lazzari, V. Arioli, and P. Bellani, J. Med. Chem. 12: 775 (1969).PubMedCrossRefGoogle Scholar
  22. 22.
    B. Cavalleri, R. Ballotta, and G. C. Lancini, J. Heterocycl. Chem. 9: 979 (1972).CrossRefGoogle Scholar
  23. 23.
    G. Asato, and G. Berkelhammer, J. Med. Chem. 15: 1086 (1972).PubMedCrossRefGoogle Scholar
  24. 24.
    B. Cavalleri, G. Volpe, V. Arioli, and G. C. Lancini, J. Med. Chem. 20: 1522 (1977).PubMedCrossRefGoogle Scholar
  25. 25.
    B. Cavalleri, G. Volpe, V. Arioli, F. Pizzocheri and A. Diena, J. Med. Chem. 21: 781 (1978).PubMedCrossRefGoogle Scholar
  26. 26.
    G. Sartori, G. C. Lancini, and B. Cavalleri, J. Labelled Compounds and Radiopharmaceuticals, XV: 673 (1978).CrossRefGoogle Scholar
  27. 27.
    W. A. Sheppard,and O. W. Webster, J. Am. Chem. Soc. 95: 2695 (1973).CrossRefGoogle Scholar
  28. 28.
    O. W. Webster, Ger. Offen. 2,3174,53, Oct. 1973 - Chem. Abstr. 80: 14926 (1974).Google Scholar
  29. 29.
    O. V. Lebedev, et al., U.S.S.R. Patent 177869, Jan. 1966 -Chem. Abstr. 64: 19630 (1966).Google Scholar
  30. 30.
    O. V. Lebedev, et al., U.S.S.R. Patent 184868, July 1966 -Chem. Abstr. 67: 9080. 9 (1967).Google Scholar
  31. 31.
    B. A. Tertov, V. V. Burykin and A.S. Morkovnik, U.S.S.R. Patent 437,763, July 1974 - Chem. Abstr. 81: 169542 (1974).Google Scholar
  32. 32.
    J. Martin, and F. Johnson, U.S. Patent 3,828,064, Aug. 1974 -Chem. Abstr. 81: 120625 (1974).Google Scholar
  33. 33.
    G. C. Cherkofsky - Europ. Patent Appl. 0,008,775 - March 1980.Google Scholar
  34. 34.
    D. P. Davis, K. L. Kirk, and L. A. Cohen, Abstracts of the “International Conference on the Chemistry, Pharmacology and Clinical Application of Nitroimidazoles”, Cesenatico (Italy) August 1980, page 52.Google Scholar
  35. 35.
    A. Lawson, J. Chem. Soc. 1955: 1695.Google Scholar
  36. 36.
    G. C. Lancini, and E. Lazzari, J. Heterocycl. Chem. 3: 152 (1966).CrossRefGoogle Scholar
  37. 37.
    M. Stagi, and A. Gianantonio, Ger. Offen. 2,600,537, July 1976- Chem. Abstr. 85: 160097 (1976).Google Scholar
  38. 38.
    W. Nagai, K. L. Kirck, and L. A. Cohen, J. Org. Chem. 38: 1971 (1973).PubMedCrossRefGoogle Scholar
  39. 39.
    T. Nishimura, and K. Kitajima, J. Org. Chem. 41:1590 (1976) ibid. 44: 818 (1979).Google Scholar
  40. 40.
    M. Ruccia, N. Vivona, and G. Cusmano, Tetrahedron, 30: 3859 (1974).CrossRefGoogle Scholar
  41. 41.
    A. G. Beaman, W. Tautz, and R. Duschinsky, Antim. Agents Chemother. 1967: 520.Google Scholar
  42. 42.
    W. Tautz, S. Teitel, and A. Brossi, J. Med. Chem. 16: 705 (1973).PubMedCrossRefGoogle Scholar
  43. 43.
    M. Hoffer, and E. Grunberg J. Med. Chem. 17: 1019 (1974).PubMedCrossRefGoogle Scholar
  44. 44.
    R. J. Rousseau, R. K. Robins, and L. B. Towsend, J. Heterocycl. Chem. 4: 311 (1967).CrossRefGoogle Scholar
  45. 45.
    B. Cavalleri, R. Ballotta, V. Arioli, and G. C. Lancini, J. Med. Chem. 16: 557 (1973).PubMedCrossRefGoogle Scholar
  46. 46.
    R. K. Sehgal, and K. C. Agrawal, J. Heterocycl. Chem. 16: 871 (1979).CrossRefGoogle Scholar
  47. 47.
    B. Cavalleri, G. Volpe, and R. Pallanza, Arzneim.-Forsch. (Drug Res.) 25: 148 (1975).Google Scholar
  48. 48.
    B. Cavalleri, G. Volpe, A. Ripamonti, and V. Arioli, Arzneim.-Forsch. (Drug Res.) 27: 1131 (1977).Google Scholar
  49. 49.
    B. Cavalleri, R. Ballotta, and V. Arioli, Arzneim.-Forsch.(Drug Res) 25: 338 (1975).Google Scholar
  50. 50.
    B. Cavalleri, G. Volpe, V. Arioli, and G. C. Lancini, Arzneim.-Forsch. (Drug Res.) 27: 1391 (1977).Google Scholar
  51. 51.
    A. Malabarba, M. Berti, A. De Paoli, and B. Cavalleri, II Farmaco, Ed. Sci. 34:105 (1979).Google Scholar
  52. 52.
    B. Cavalleri, G. Volpe, V. Arioli, J. Med. Chem. 20: 656 (1977).PubMedCrossRefGoogle Scholar
  53. 53.
    H. Berger, R. Gall, K. Stach, W. Voemel, and R. Hoffmann, Ger. Offen. 2,261,693, June 1974 - Chem. Abstr. 81: 120674 (1974).Google Scholar
  54. 54.
    R. G. Fargher and F. L. Pyman, J. Chem. Soc. 115:217 (1919) ibid. 115: 234 (1919).Google Scholar
  55. 55.
    M. W. Miller, H. L. Howes Jr., R. V. Kasubick, and A. R. English J. Med. Chem. 13: 849 (1970).PubMedCrossRefGoogle Scholar
  56. 56.
    A. Zmojdzin et al. Pol. Patent 92,065, Dec. 1977 - Chem. Abstr. 90: 87460 (1979).Google Scholar
  57. 57.
    J. S. Amato, V.J. Grenda, T. M. H. Liu, and E. J. J. Grabowski, J. Heterocycl. Chem. 16: 1153 (1979).CrossRefGoogle Scholar
  58. 58.
    W. A. Remers, G. J. Gibs, and M. J. Weiss, J. Heterocycl. Chem. 6: 835 (1969).CrossRefGoogle Scholar
  59. 59.
    K. Butler, H. L. Howes, J. E. Lynch, and D. K. Pirie, J. Med. Chem. 10: 891 (1967).PubMedCrossRefGoogle Scholar
  60. 60.
    G. P. Ellis, C. Epstein, C. Fitzmaurice, L. Goldberg, and G. H. Lord J. Pharm. Pharmacol. 16:801 (1966), ibid 19: 102 (1967).Google Scholar
  61. 61.
    P. Melloni, E. Dradi, W. Logemann, I. de Carrieri, and F. Trane, J, Med. Chem. 15: 926 (1972).Google Scholar
  62. 62.
    P. Melloni, R. Metelli, De. Fusar Bassini, C. Confalonieri, W. Logemann, I. de Carneri, and F. Trane, Arzneim.-Forsch. (Drug Res.) 25: 9 (1975).Google Scholar
  63. 63.
    Merck and Co. Inc., Neth. Appl. 66,09553, Jan. 1967 - Chem. Abstr. 67: 11487 (1967).Google Scholar
  64. 64.
    R. C. Tweit, E. M. Kreider, and R. D. Muir, J. Med. Chem. 16: 1161 (1973).PubMedCrossRefGoogle Scholar
  65. 65.
    C. E. Hazeldine, F. L. Pyman, and J. Winchester, J. Chem. Soc. 1924: 1431.Google Scholar
  66. 66.
    M. Hoffer, M. Mitrovic, A. Beaman, and A. Brossi, J. Med. Chem. 14: 993 (1971).PubMedGoogle Scholar
  67. 67.
    E. J. J. Grabowski, T. M. H. Liu, L. Salce, and E. F. Schoenewaldt, J. Med. Chem. 17: 547 (1974).PubMedCrossRefGoogle Scholar
  68. 68.
    M. Hoffer, V. Toome, and A. Brossi, J. Heterocycl. Chem. 3: 454 (1966).CrossRefGoogle Scholar
  69. 69.
    M. Hoffer, and A. MacDonald Jr., U.S. Patent 3,652,579, March 1972 - Chem. Abstr. 76: 153741 (1972).Google Scholar
  70. 70.
    W. G. Forsyth, and F. L. Pyman, J. Chem. Soc. 1925: 573.Google Scholar
  71. 71.
    A. Grimison, and В. V. Smith, Chem. Ind. (London) 1956: 983.Google Scholar
  72. 72.
    A. Grimison, J. H. Ridd and В. V. Smith, J. Chem. Soc. 1960: 1352; ibid. 1960: 1357.Google Scholar
  73. 73.
    J. H. Ridd, and В. V. Smith, J. Chem. Soc. 1960: 1363.Google Scholar
  74. 74.
    E. Laviron, Bull. Soc. Chim. France 1963: 2840.Google Scholar
  75. 75.
    F. Kajfež, D. Kolbah, M. Oklobdžija, T. Fajdiga, M. Slamnik, and V. Šunjić, Croat. Chem. Acta. 39: 199 (1967)Google Scholar
  76. 76.
    F. Kajfež, V. Šunjić, D. Kolbah, T. Fajdiga, and H. Oklobdžija, J. Med. Chem. 11: 167 (1968).PubMedCrossRefGoogle Scholar
  77. 77.
    V. Šunjić, D. Kolbah, F. Kajfež, and N. Blažević J. Med. Chem. 11: 1264 (1968).PubMedCrossRefGoogle Scholar
  78. 78.
    P. N. Giraldi, V. Mariotti, G. Nannini, G. P. Tosolini, E. Dradi, W. Logemann, I. de Carneri, and G. Monti Arzneim.- Forsch. (Drug Res.) 20: 52 (1970).Google Scholar
  79. 79.
    P. N. Giraldi, V. Mariotti, and I. de Carneri, J. Med. Chem. 11: 66 (1968).CrossRefGoogle Scholar
  80. 80.
    W. J.. Ross,and A. Todd J. Med. Chem. 16: 863 (1973).CrossRefGoogle Scholar
  81. 81.
    B. S. Huang, J. M. Lauzon, and J. C. Parham, J. Heterocycl. Chem. 16: 811 (1979).CrossRefGoogle Scholar
  82. 82.
    C. Chavis, F. Grodenic, and J. L. Imbach, Eur. J. Med. Chem. 14: 123 (1979).Google Scholar
  83. 83.
    S. S. Berg, and B. W. Sharp, Eur. J. Med. Chem. 10: 171 (1975).Google Scholar
  84. 84.
    V. Kaplar, V. Šunjić, and F. KajfeX J. Heterocycl. Chem. 11:1055 (1974).CrossRefGoogle Scholar
  85. 85.
    V. Šunjić, T. Fajdiga, N. Blazevic, and F. Kaifež Acta Pharm. Jug. 19: 65 (1969).Google Scholar
  86. 86.
    J. Heeres, J. H. Mostmans, B. Maes, and L. J. J. Backx, Eur. J. Med. Chem. 11: 237 (1976).Google Scholar
  87. 87.
    V. Šunjić, F. Kaijfez, D. Kolbah, and N. Blazevic Die Pharmazie 27:131 (1972), and literature cited.Google Scholar
  88. 88.
    D. W. Henry, and R. D. Hoff, Belg. Patent 661,262, Sept. 1965 -Chem. Abstr. 64:2093 (19651.Google Scholar
  89. 89.
    G. Asato, and J. English., U.S. Patent 3,565,892, Feb. 1979 -Chem. Abstr. 75: 36041 (1971).Google Scholar
  90. 90.
    C. Rufer, H.-J. Kessler, and E. Schröder J. Med. Chem. 14: 94 (1971).PubMedCrossRefGoogle Scholar
  91. 91.
    R. E. Bambury, C. M. Lutz, L. F. Miller, H. K. Kim, and H. W. Ritter, J. Med. Chem. 16: 566 (1973).PubMedCrossRefGoogle Scholar
  92. 92.
    C. Rufer, and H.-J. Kessler, Chim. Ther. 7: 122 (1972).Google Scholar
  93. 93.
    C. Rufer, and K. Schwarz Liebigs Ann. Chem. 1975: 1465.Google Scholar
  94. 94.
    May and Baker Ltd., Belg. Patent 639,469, April 1964 - Chem. Abstr. 62:9142 Ц965).Google Scholar
  95. 95.
    E. Winkelmann, and H. Kroha Ger. Offen. 2,425,292, Dec. 1975 - Chem. Abstr. 85: 123919 C1976 ).Google Scholar
  96. 96.
    Merck and Co. Inc., Neth. Appl. 64,13814, May 1965 - Chem. Abstr. 63: 18097 C1965 ).Google Scholar
  97. 97.
    J. M. Chemerda, J. Kollonitsch, and S. Marburg, U.S. Patent 3,548,007, June 1971 - Chem. Abstr. 75: 49081 (1971).Google Scholar
  98. 98.
    Merck and Co. Inc., Neth. Appl. 65,03901, Sept. 1965 - Chem. Abstr. 64:12683 (19661.Google Scholar
  99. 99.
    Merck and Co. Inc., Neth. Appl. 64,09117, Feb. 1965 - Chem. Abstr. 63:606 CL965).Google Scholar
  100. 100.
    C. Rufer, H.-J. Kessler, and E. Schröder Chim. Ther. 6: 286 (1971).Google Scholar
  101. 101.
    E. Winkelmann, W. Raether, U. Gebert, and A. Sinharay, Arzneim-Forsch. (Drug Res.) 27: 2251 (1977).Google Scholar
  102. 102.
    E. Winkelmann, W. Raether, and A. Sinharay, Arzneim.-Forsch. (Drug Res.) 28: 351 (1978).Google Scholar
  103. 103.
    E. Winkelmann, and W. Raether Arzneim.-Forsch. (Drug Res.) 28: 739 (1978).Google Scholar
  104. 104.
    E. Winkelmann, W. Raether, and U. -Gebert, Arzneim.-Forsch. (Drug Res.) 28: 1682 (1978).Google Scholar
  105. 105.
    G. Asato, and G. Berkelhammer, U.S. Patent 3,795,735 March 1974 - Chem. Abstr. 80: 120959 (1974).Google Scholar
  106. 106.
    H.-J. Kessler, C. Rufer, and K. Schwarz, Eur. J. Med. Chem. 11:19 (1976)%Google Scholar
  107. 107.
    C. Rufer, H.-J. Kessler, and E. Schröder J. Med. Chem. 14: 934 (1971).PubMedCrossRefGoogle Scholar
  108. 108.
    G. Berkelhammer, and G. Asato, U.S. Patent 3,740,434, June 1973- Chem. Abstr. 79: 66365 (1973).Google Scholar
  109. 109.
    J. P. Verge, M. C. Neville, and H. Friedman, Ger. Offen. 2,431, 775, Feb. 1975 - Chem. Abstr. 83: 10079 (1975).Google Scholar
  110. 110.
    C. Rufer, H.-J. Kessler, E. Schröder, and A. Damerius, Chim. Ther. 8: 567 (1973).Google Scholar
  111. 111.
    C. Rufer, H.-J. Kessler, and E. Schröder, J. Med. Chem. 18: 253 (1975).PubMedCrossRefGoogle Scholar
  112. 112.
    C. Rufer, H.-J. Kessler, E. Schrôder, and A. Damerius, Chim. Ther. 7: 5 (1972).Google Scholar
  113. 113.
    M. T. Wu, J. Heterocycl. Chem. 9: 31 (1972).CrossRefGoogle Scholar
  114. 114.
    H. Berger, R. Gall, and K. Stach, Ger. Offen, 2,261,735, June 1974 - Chem. Abstr. 81: 120673 (1974).Google Scholar

Copyright information

© Plenum Press, New York 1982

Authors and Affiliations

  • Bruno Cavalleri
    • 1
  1. 1.Research LaboratoriesGruppo Lepetit S.p.A.MilanoItaly

Personalised recommendations