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Nitroimidazoles pp 9–33Cite as

Nitroimidazole Chemistry I: Synthetic Methods

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Part of the book series: NATO Advanced Study Institutes 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.

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References

  1. H. Horie, J. Antibiotics Ser. A. 9: 168 (1956).

    CAS  Google Scholar 

  2. S. Nakamura, Pharm. Bull. 3: 379 (1955).

    PubMed  CAS  Google Scholar 

  3. K. Maeda, T. Osato, and H. Umezawa, J. Antibiotics, Ser. A. 6: 182 (1953).

    CAS  Google Scholar 

  4. G. C. Lancini, N. Maggi, and P. Sensi, II. Farmaco, Ed. Sci. 18:390 (1963).

    CAS  Google Scholar 

  5. F. Rung, and M. Behrend, Ann. 271: 28 (1892).

    Google Scholar 

  6. A. Windaus, Ber. 42: 758 (1909).

    CAS  Google Scholar 

  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. C. Cosar, C. Crisan, R. Horclois, R. M. Jacob, S. Tchelitcheff, and R. Vaupré, Arzneim-Forsch.(Drug. Res.), 16: 23 (1966).

    CAS  Google Scholar 

  9. K.C. Agrawal, K.B. Bears, and R. K. Sehgal, J. Med. Chem. 22: 583 (1979).

    Article  PubMed  CAS  Google Scholar 

  10. R. K. Sehgal, and K. C. Agrawal, J. Heterocycl. Chem. 16: 1499 (1979).

    Article  CAS  Google Scholar 

  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. K. Hofmann, “Imidazole and Its Derivatives”, Part I, in: “The Chemistry of Heterocyclic Compounds”, Interscience Publishers Inc., New York (1953).

    Google Scholar 

  13. G. C. Lancini, D. Kluepfel, E. Lazzari, and G. Sartori, Biochim. Biophys. Acta, 130: 37 (1966).

    Article  CAS  Google Scholar 

  14. Y. Seki, T. Nakamura, and Y. Okami, Biochem. J. 67: 389 (1970).

    CAS  Google Scholar 

  15. G. C. Lancini, E. Lazzari, and G. Sartori, J. Antibiotics 6: 387 (1968).

    Article  Google Scholar 

  16. A. F. Pozharskii, E. A. Zvezdina, and A. M. Simonov, Tetrahedron Letters, 23: 2219 (1967).

    Article  PubMed  CAS  Google Scholar 

  17. M. D. Coburn, J. Heterocycl. Chem. 7: 455 (1970).

    Article  CAS  Google Scholar 

  18. G. C. Lancini, and E. Lazzari, Experientia 21: 1 (1965).

    Article  Google Scholar 

  19. A. G. Beaman, W. Tautz, T. Gabriel, and R. Duschinsky, J. Am. Chem. Soc. 87: 389 (1965).

    Article  PubMed  CAS  Google Scholar 

  20. A. G. Beaman, W. Tautz, T. Gabriel, 0. Keller, V. Toome, and T. Duschinsky, Antim. Agents Chemother. 1965: 469

    Google Scholar 

  21. G. C. Lancini, E. Lazzari, V. Arioli, and P. Bellani, J. Med. Chem. 12: 775 (1969).

    Article  PubMed  CAS  Google Scholar 

  22. B. Cavalleri, R. Ballotta, and G. C. Lancini, J. Heterocycl. Chem. 9: 979 (1972).

    Article  CAS  Google Scholar 

  23. G. Asato, and G. Berkelhammer, J. Med. Chem. 15: 1086 (1972).

    Article  PubMed  CAS  Google Scholar 

  24. B. Cavalleri, G. Volpe, V. Arioli, and G. C. Lancini, J. Med. Chem. 20: 1522 (1977).

    Article  PubMed  CAS  Google Scholar 

  25. B. Cavalleri, G. Volpe, V. Arioli, F. Pizzocheri and A. Diena, J. Med. Chem. 21: 781 (1978).

    Article  PubMed  CAS  Google Scholar 

  26. G. Sartori, G. C. Lancini, and B. Cavalleri, J. Labelled Compounds and Radiopharmaceuticals, XV: 673 (1978).

    Article  Google Scholar 

  27. W. A. Sheppard,and O. W. Webster, J. Am. Chem. Soc. 95: 2695 (1973).

    Article  CAS  Google Scholar 

  28. O. W. Webster, Ger. Offen. 2,3174,53, Oct. 1973 - Chem. Abstr. 80: 14926 (1974).

    Google Scholar 

  29. O. V. Lebedev, et al., U.S.S.R. Patent 177869, Jan. 1966 -Chem. Abstr. 64: 19630 (1966).

    Google Scholar 

  30. O. V. Lebedev, et al., U.S.S.R. Patent 184868, July 1966 -Chem. Abstr. 67: 9080. 9 (1967).

    Google Scholar 

  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. J. Martin, and F. Johnson, U.S. Patent 3,828,064, Aug. 1974 -Chem. Abstr. 81: 120625 (1974).

    Google Scholar 

  33. G. C. Cherkofsky - Europ. Patent Appl. 0,008,775 - March 1980.

    Google Scholar 

  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. A. Lawson, J. Chem. Soc. 1955: 1695.

    Google Scholar 

  36. G. C. Lancini, and E. Lazzari, J. Heterocycl. Chem. 3: 152 (1966).

    Article  CAS  Google Scholar 

  37. M. Stagi, and A. Gianantonio, Ger. Offen. 2,600,537, July 1976- Chem. Abstr. 85: 160097 (1976).

    Google Scholar 

  38. W. Nagai, K. L. Kirck, and L. A. Cohen, J. Org. Chem. 38: 1971 (1973).

    Article  PubMed  CAS  Google Scholar 

  39. T. Nishimura, and K. Kitajima, J. Org. Chem. 41:1590 (1976) ibid. 44: 818 (1979).

    CAS  Google Scholar 

  40. M. Ruccia, N. Vivona, and G. Cusmano, Tetrahedron, 30: 3859 (1974).

    Article  CAS  Google Scholar 

  41. A. G. Beaman, W. Tautz, and R. Duschinsky, Antim. Agents Chemother. 1967: 520.

    Google Scholar 

  42. W. Tautz, S. Teitel, and A. Brossi, J. Med. Chem. 16: 705 (1973).

    Article  PubMed  CAS  Google Scholar 

  43. M. Hoffer, and E. Grunberg J. Med. Chem. 17: 1019 (1974).

    Article  PubMed  CAS  Google Scholar 

  44. R. J. Rousseau, R. K. Robins, and L. B. Towsend, J. Heterocycl. Chem. 4: 311 (1967).

    Article  CAS  Google Scholar 

  45. B. Cavalleri, R. Ballotta, V. Arioli, and G. C. Lancini, J. Med. Chem. 16: 557 (1973).

    Article  PubMed  CAS  Google Scholar 

  46. R. K. Sehgal, and K. C. Agrawal, J. Heterocycl. Chem. 16: 871 (1979).

    Article  CAS  Google Scholar 

  47. B. Cavalleri, G. Volpe, and R. Pallanza, Arzneim.-Forsch. (Drug Res.) 25: 148 (1975).

    CAS  Google Scholar 

  48. B. Cavalleri, G. Volpe, A. Ripamonti, and V. Arioli, Arzneim.-Forsch. (Drug Res.) 27: 1131 (1977).

    CAS  Google Scholar 

  49. B. Cavalleri, R. Ballotta, and V. Arioli, Arzneim.-Forsch.(Drug Res) 25: 338 (1975).

    CAS  Google Scholar 

  50. B. Cavalleri, G. Volpe, V. Arioli, and G. C. Lancini, Arzneim.-Forsch. (Drug Res.) 27: 1391 (1977).

    CAS  Google Scholar 

  51. A. Malabarba, M. Berti, A. De Paoli, and B. Cavalleri, II Farmaco, Ed. Sci. 34:105 (1979).

    CAS  Google Scholar 

  52. B. Cavalleri, G. Volpe, V. Arioli, J. Med. Chem. 20: 656 (1977).

    Article  PubMed  CAS  Google Scholar 

  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. R. G. Fargher and F. L. Pyman, J. Chem. Soc. 115:217 (1919) ibid. 115: 234 (1919).

    Google Scholar 

  55. M. W. Miller, H. L. Howes Jr., R. V. Kasubick, and A. R. English J. Med. Chem. 13: 849 (1970).

    Article  PubMed  CAS  Google Scholar 

  56. A. Zmojdzin et al. Pol. Patent 92,065, Dec. 1977 - Chem. Abstr. 90: 87460 (1979).

    Google Scholar 

  57. J. S. Amato, V.J. Grenda, T. M. H. Liu, and E. J. J. Grabowski, J. Heterocycl. Chem. 16: 1153 (1979).

    Article  CAS  Google Scholar 

  58. W. A. Remers, G. J. Gibs, and M. J. Weiss, J. Heterocycl. Chem. 6: 835 (1969).

    Article  CAS  Google Scholar 

  59. K. Butler, H. L. Howes, J. E. Lynch, and D. K. Pirie, J. Med. Chem. 10: 891 (1967).

    Article  PubMed  CAS  Google Scholar 

  60. G. P. Ellis, C. Epstein, C. Fitzmaurice, L. Goldberg, and G. H. Lord J. Pharm. Pharmacol. 16:801 (1966), ibid 19: 102 (1967).

    CAS  Google Scholar 

  61. P. Melloni, E. Dradi, W. Logemann, I. de Carrieri, and F. Trane, J, Med. Chem. 15: 926 (1972).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  63. Merck and Co. Inc., Neth. Appl. 66,09553, Jan. 1967 - Chem. Abstr. 67: 11487 (1967).

    Google Scholar 

  64. R. C. Tweit, E. M. Kreider, and R. D. Muir, J. Med. Chem. 16: 1161 (1973).

    Article  PubMed  CAS  Google Scholar 

  65. C. E. Hazeldine, F. L. Pyman, and J. Winchester, J. Chem. Soc. 1924: 1431.

    Google Scholar 

  66. M. Hoffer, M. Mitrovic, A. Beaman, and A. Brossi, J. Med. Chem. 14: 993 (1971).

    PubMed  CAS  Google Scholar 

  67. E. J. J. Grabowski, T. M. H. Liu, L. Salce, and E. F. Schoenewaldt, J. Med. Chem. 17: 547 (1974).

    Article  PubMed  CAS  Google Scholar 

  68. M. Hoffer, V. Toome, and A. Brossi, J. Heterocycl. Chem. 3: 454 (1966).

    Article  CAS  Google Scholar 

  69. M. Hoffer, and A. MacDonald Jr., U.S. Patent 3,652,579, March 1972 - Chem. Abstr. 76: 153741 (1972).

    Google Scholar 

  70. W. G. Forsyth, and F. L. Pyman, J. Chem. Soc. 1925: 573.

    Google Scholar 

  71. A. Grimison, and В. V. Smith, Chem. Ind. (London) 1956: 983.

    Google Scholar 

  72. A. Grimison, J. H. Ridd and В. V. Smith, J. Chem. Soc. 1960: 1352; ibid. 1960: 1357.

    Google Scholar 

  73. J. H. Ridd, and В. V. Smith, J. Chem. Soc. 1960: 1363.

    Google Scholar 

  74. E. Laviron, Bull. Soc. Chim. France 1963: 2840.

    Google Scholar 

  75. F. Kajfež, D. Kolbah, M. Oklobdžija, T. Fajdiga, M. Slamnik, and V. Šunjić, Croat. Chem. Acta. 39: 199 (1967)

    Google Scholar 

  76. F. Kajfež, V. Šunjić, D. Kolbah, T. Fajdiga, and H. Oklobdžija, J. Med. Chem. 11: 167 (1968).

    Article  PubMed  Google Scholar 

  77. V. Šunjić, D. Kolbah, F. Kajfež, and N. Blažević J. Med. Chem. 11: 1264 (1968).

    Article  PubMed  CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  79. P. N. Giraldi, V. Mariotti, and I. de Carneri, J. Med. Chem. 11: 66 (1968).

    Article  CAS  Google Scholar 

  80. W. J.. Ross,and A. Todd J. Med. Chem. 16: 863 (1973).

    Article  CAS  Google Scholar 

  81. B. S. Huang, J. M. Lauzon, and J. C. Parham, J. Heterocycl. Chem. 16: 811 (1979).

    Article  CAS  Google Scholar 

  82. C. Chavis, F. Grodenic, and J. L. Imbach, Eur. J. Med. Chem. 14: 123 (1979).

    CAS  Google Scholar 

  83. S. S. Berg, and B. W. Sharp, Eur. J. Med. Chem. 10: 171 (1975).

    CAS  Google Scholar 

  84. V. Kaplar, V. Šunjić, and F. KajfeX J. Heterocycl. Chem. 11:1055 (1974).

    Article  Google Scholar 

  85. V. Šunjić, T. Fajdiga, N. Blazevic, and F. Kaifež Acta Pharm. Jug. 19: 65 (1969).

    CAS  Google Scholar 

  86. J. Heeres, J. H. Mostmans, B. Maes, and L. J. J. Backx, Eur. J. Med. Chem. 11: 237 (1976).

    CAS  Google Scholar 

  87. V. Šunjić, F. Kaijfez, D. Kolbah, and N. Blazevic Die Pharmazie 27:131 (1972), and literature cited.

    Google Scholar 

  88. D. W. Henry, and R. D. Hoff, Belg. Patent 661,262, Sept. 1965 -Chem. Abstr. 64:2093 (19651.

    Google Scholar 

  89. G. Asato, and J. English., U.S. Patent 3,565,892, Feb. 1979 -Chem. Abstr. 75: 36041 (1971).

    Google Scholar 

  90. C. Rufer, H.-J. Kessler, and E. Schröder J. Med. Chem. 14: 94 (1971).

    Article  PubMed  CAS  Google Scholar 

  91. R. E. Bambury, C. M. Lutz, L. F. Miller, H. K. Kim, and H. W. Ritter, J. Med. Chem. 16: 566 (1973).

    Article  PubMed  CAS  Google Scholar 

  92. C. Rufer, and H.-J. Kessler, Chim. Ther. 7: 122 (1972).

    CAS  Google Scholar 

  93. C. Rufer, and K. Schwarz Liebigs Ann. Chem. 1975: 1465.

    Google Scholar 

  94. May and Baker Ltd., Belg. Patent 639,469, April 1964 - Chem. Abstr. 62:9142 Ц965).

    Google Scholar 

  95. E. Winkelmann, and H. Kroha Ger. Offen. 2,425,292, Dec. 1975 - Chem. Abstr. 85: 123919 C1976 ).

    Google Scholar 

  96. Merck and Co. Inc., Neth. Appl. 64,13814, May 1965 - Chem. Abstr. 63: 18097 C1965 ).

    Google Scholar 

  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. Merck and Co. Inc., Neth. Appl. 65,03901, Sept. 1965 - Chem. Abstr. 64:12683 (19661.

    Google Scholar 

  99. Merck and Co. Inc., Neth. Appl. 64,09117, Feb. 1965 - Chem. Abstr. 63:606 CL965).

    Google Scholar 

  100. C. Rufer, H.-J. Kessler, and E. Schröder Chim. Ther. 6: 286 (1971).

    CAS  Google Scholar 

  101. E. Winkelmann, W. Raether, U. Gebert, and A. Sinharay, Arzneim-Forsch. (Drug Res.) 27: 2251 (1977).

    CAS  Google Scholar 

  102. E. Winkelmann, W. Raether, and A. Sinharay, Arzneim.-Forsch. (Drug Res.) 28: 351 (1978).

    CAS  Google Scholar 

  103. E. Winkelmann, and W. Raether Arzneim.-Forsch. (Drug Res.) 28: 739 (1978).

    Google Scholar 

  104. E. Winkelmann, W. Raether, and U. -Gebert, Arzneim.-Forsch. (Drug Res.) 28: 1682 (1978).

    CAS  Google Scholar 

  105. G. Asato, and G. Berkelhammer, U.S. Patent 3,795,735 March 1974 - Chem. Abstr. 80: 120959 (1974).

    Google Scholar 

  106. H.-J. Kessler, C. Rufer, and K. Schwarz, Eur. J. Med. Chem. 11:19 (1976)%

    Google Scholar 

  107. C. Rufer, H.-J. Kessler, and E. Schröder J. Med. Chem. 14: 934 (1971).

    Article  PubMed  CAS  Google Scholar 

  108. G. Berkelhammer, and G. Asato, U.S. Patent 3,740,434, June 1973- Chem. Abstr. 79: 66365 (1973).

    Google Scholar 

  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. C. Rufer, H.-J. Kessler, E. Schröder, and A. Damerius, Chim. Ther. 8: 567 (1973).

    CAS  Google Scholar 

  111. C. Rufer, H.-J. Kessler, and E. Schröder, J. Med. Chem. 18: 253 (1975).

    Article  PubMed  CAS  Google Scholar 

  112. C. Rufer, H.-J. Kessler, E. Schrôder, and A. Damerius, Chim. Ther. 7: 5 (1972).

    CAS  Google Scholar 

  113. M. T. Wu, J. Heterocycl. Chem. 9: 31 (1972).

    Article  CAS  Google Scholar 

  114. H. Berger, R. Gall, and K. Stach, Ger. Offen, 2,261,735, June 1974 - Chem. Abstr. 81: 120673 (1974).

    Google Scholar 

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Authors and Affiliations

  1. Research Laboratories, Gruppo Lepetit S.p.A., Via Durando 38, 20158, Milano, Italy

    Bruno Cavalleri

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  1. Bruno Cavalleri
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Editors and Affiliations

  1. University of Bologna, Bologna, Italy

    A. Breccia

  2. Gruppo Lepetit SpA, Milan, Italy

    B. Cavalleri

  3. Institute of Cancer Research, Sutton, England

    G. E. Adams

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Cavalleri, B. (1982). Nitroimidazole Chemistry I: Synthetic Methods. In: Breccia, A., Cavalleri, B., Adams, G.E. (eds) Nitroimidazoles. NATO Advanced Study Institutes Series, vol 42. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-4151-2_2

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