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Fluorine-Containing Benzimidazoles and Their [a]- and [b]Heteroannelated Derivatives: Synthesis and Biological Activity (Review)

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Chemistry of Heterocyclic Compounds Aims and scope

Published data from 1992-2013 on methods for the synthesis and biological activity of fluorine-containing benzimidazoles and their [a]- and [b]heteroannelated derivatives are summarized and classified.

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References

  1. M. D. Mashkovskii, Drugs [in Russian], Vol. 1, 2, Novaya Volna, Moscow (2002).

  2. T. Andersson, Clin. Pharmacokinet., 31, 9 (1996).

    Article  CAS  Google Scholar 

  3. V. C. Emery and A. F. Hassan-Walker, Drugs, 62, 1853 (2002).

    Article  CAS  Google Scholar 

  4. H. Kagechika, Curr. Med. Chem., 9, 591 (2002).

    Article  CAS  Google Scholar 

  5. H. Vanden Bossche, M. Engelen, and F. Rochette, J. Vet. Pharmacol. Ther., 26, 5 (2003).

    Article  CAS  Google Scholar 

  6. E. V. Nosova, G. N. Lipunova, V. N. Charushin, and O. N. Chupakhin, Fluorine-containing Azines and Benzazines [in Russian], Izd. UrO RAN, Yekaterinburg (2011).

    Google Scholar 

  7. D. Bouzard, in: R. Krohn, H. A. Kirst, and H. Maag (editors), Antibiotics and Antiviral Compounds. Chemical Synthesis and Modification, VCH Publishers, Inc., New York (1993), p. 187.

    Google Scholar 

  8. A. E. Klopffer and J. W. Engels, Nucleosides, Nucleotides Nucleic Acids, 22, 1347 (2003).

    Article  CAS  Google Scholar 

  9. K. Kubo, Y. Kohara, Y. Yoshimura, Y. Inada, Y. Shibouta, Y. Furukawa, T. Kato, K. Nishikawa, and T. Naka, J. Med. Chem., 36, 2343 (1993).

    Article  CAS  Google Scholar 

  10. D. V. Fedyuk, I. I. Maletina, and L. M. Yagupolskii, Ukr. Khim. Zh., 63, No. 9, 29 (1997).

    CAS  Google Scholar 

  11. M. R. Grimmett, in: R. Neier (editor), Science of Synthesis: Houben-Weyl Methods of Molecular Transformations. Category 2, Hetarenes and Related Ring Systems. Vol. 12. Five-Membered Hetarenes with Two Nitrogen or Phosphorus Atoms, Thieme, New York (2002), p. 529.

    Google Scholar 

  12. K. C. Joshi, R. Jain, and A. Dandia, J. Fluorine Chem., 56, 1 (1992).

    Article  CAS  Google Scholar 

  13. J. Vilarrasa, C. Galvez, and M. Calafell, An. Quim., 71, 631 (1975).

    CAS  Google Scholar 

  14. M.-J. Camarasa, P. L. Coe, A. S. Jones, and R. T. Walker, J. Chem. Soc., Perkin Trans. 1, 2317 (1987).

  15. S. K. Kotovskaya, N. M. Perova, Z. M. Baskakova, S. A. Romanova, V. N. Charushin, and O. N. Chupakhin, Zh. Org. Khim., 37, 598 (2001). [Russ. J. Org. Chem., 37, 564 (2001).]

  16. K. Takatori, Y. Yamada, T. Arai, and R. Nakazawa, Yakugaku Zasshi, 78, 108 (1958).

    CAS  Google Scholar 

  17. J. A. Montgomery and K. Hewson, J. Med. Chem., 8, 737 (1965).

    Article  CAS  Google Scholar 

  18. B. M. O'Neill, J. E. Ratto, K. L. Good, D. C. Tahmassebi, S. A. Helquist, J. C. Morales, and E. T. Kool, J. Org. Chem., 67, 5869 (2002).

    Article  Google Scholar 

  19. X. Huang, X. Dong, C. Yin, B. Huang, F. Qu, and M. Cheng, Wuhan Daxue, Ziran Kexueban, 4, 123 (1993).

    Google Scholar 

  20. G. A. Bistocchi, G. De Meo, M. Pedini, A. Ricci, and P. Jacquignon, Collect. Czech. Chem. Commun., 50, 1959 (1985).

    Article  CAS  Google Scholar 

  21. Z. Liu, H. Li, Q. Zhao, and J. Shen, Heterocycles, 75, 1907 (2008).

    Article  CAS  Google Scholar 

  22. Z. Kazimierczuk, L. Dudycz, R. Stolarski, and D. Shugar, J. Carbohydr., Nucleosides, Nucleotides, 8, 101 (1981).

  23. L. Li, G. Liu, Z. G. Wang, Y. Y. Yuan, C. X. Zhang, X. H. Wu, and J. Zhang, J. Comb. Chem., 6, 811 (2004).

    Article  CAS  Google Scholar 

  24. L. Wu and G. Liu, Chin. J. Chem., 29, 983 (2011).

    Article  Google Scholar 

  25. G. K. Surya Prakash, T. Mathew, Ch. Panja, H. Vaghoo, K. Venkataraman, and G. A. Olah, Org. Lett., 9, 179 (2007).

    Article  Google Scholar 

  26. I. W. Harvey, M. D. McFarlane, D. J. Moody, and D. M. Smith, J. Chem. Soc., Perkin Trans. 1, 681 (1988).

  27. P. A. Collins Cafiero, C. S. French, M. D. McFarlane, R. K. Mackie, and D. M. Smith, J. Chem. Soc., Perkin Trans 1, 1375 (1997).

  28. A. Rosegay, Drug Metab. Dispos., 8, 136 (1980).

    CAS  Google Scholar 

  29. S. Robev, Dokl. Bolg. Akad. Nauk, 34, 663 (1981).

    CAS  Google Scholar 

  30. O. Axelsson, D. Peters, E. O. Nielsen, and P. Christophersen, Eur. Pat. Appl. 0563001.

  31. I. Neagu, D. Diller, C. Kingsbury, A. C. Bohnstedt, M. J. Ohlmeyer, V. Paradkar, and N. Ansari, WO Pat. Appl. 2010022358.

  32. A. G. Cole, A. C. Bohnstedt, V. Paradkar, C. Kingsbury, J. G. Quintero, H. Park, Y. Lu, M. You, I. Neagu, D. Diller, J. J. Letourneau, Y. Shao, R. A. James, C. M. Riviello, K.-K. Ho, T. H. Lin, B. Wang, K. C. Appell, M. Sills, E. Quadros, E. F. Kimble, M. H. J. Ohlmeyer, and M. L. Webb, Bioorg. Med. Chem. Lett., 19, 6788 (2009).

    Article  CAS  Google Scholar 

  33. M. Morgenthaler, J. D. Aebi, F. Grüninger, D. Mona, B. Wagner, M. Kansy, and F. Diederich, J. Fluorine Chem., 129, 852 (2008).

    Article  CAS  Google Scholar 

  34. J. M. Dener, C. O'Bryan, R. Yee, E. J. Shelton, D. Sperandio, T. Mahajan, J. T. Palmer, J. R. Spencer, and Z. Tong, Tetrahedron Lett., 47, 4591 (2006).

    Article  CAS  Google Scholar 

  35. S. D. Barrett, A. J. Bridges, and H. Tecle, WO Pat. Appl. 0042022.

  36. S. D. Barrett, A. J. Bridges, H. Tecle, A. Dixon, K. Lee, and R. D. Pinnock, WO Pat. Appl. 0105390.

  37. E. M. Wallace, J. P. Lyssikatos, A. L. Marlow, T. B. Hurley, and K. Koch, US Pat. Appl. 2004116710.

  38. S. D. Barrett, C. M. Flamme, M. D. Kaufman, J. B. Milbank, H. Tecle, and J. S. Warmus, WO Pat. Appl. 2005009975.

  39. J. Demattei, S. Shakya, A. D. Piscopio, B. P. Hache, M. C. Evans, J. G. Ford, S. M. Pointon, K. Peeters, T. J. Lilley, and J. Leonard, WO Pat. Appl. 2007002157.

  40. J. Demattei, S. Shakya, P. J. Nichols, B. R. Barnett, B. P. Hache, M. C. Evans, J. G. Ford, and J. Leonard, WO Pat. Appl. 2007002092.

  41. R. J. Roberts, R. A. Storey, M. Pervez, and C. J. Squire, WO Pat. Appl. 2007071951.

  42. N. F. Bateman, P. R. Gellert, and K. J. Hill, WO Pat. Appl. 2009118562.

  43. O. Krieter, P. M. Susa, G. Caponigro, and M. Wartman, WO Pat. Appl. 2012145503.

  44. Q. Zeng, R. G. Aslanian, M. Y. Berlin, C. W. Boyce, J. Cao, J. A. Kozlowski, P. Mangiaracina, K. D. McCormick, M. W. Mutahi, S. B. Rosenblum, N.-Y. Shih, D. M. Solomon, and W. C. Tom, WO Pat. Appl. 03088967.

  45. M. Van Heek, J. J. Hwa, M. P. Graziano, J. E. Lachowicz, T. J. Kowalski, E. P. Veltri, K. D. McCormick, M. Y. Berlin, and R. G. Aslanian, US Pat. Appl. 2007142369.

  46. R. G. Aslanian, J. E. Lachowicz, M. Y. Berlin, and J. J. Hwa, WO Pat. Appl. 2008108958.

  47. W. Brown, S. Johnstone, and D. Labrecque, WO Pat. Appl. 2008018827.

  48. S. Das, A. Thomas, N. Khairatkar-Joshi, and M. Bajpai, WO Pat. Appl. 2012131501.

  49. W. L. Wu, D. A. Burnett, and M. A. Caplen, US Pat. Appl. 2005049269.

  50. W.-L. Wu, D. A. Burnett, M. A. Caplen, M. S. Domalski, C. Bennett, W. J. Greenlee, B. E. Hawes, K. O'Neill, B. Weig, D. Weston, B. Spar, and T. Kowalski, Bioorg. Med. Chem. Lett., 16, 3674 (2006).

    Article  CAS  Google Scholar 

  51. S. He, Q. Hong, Z. Lai, Z. Wu, Y. Yu, D. W. Kim, P. C. Ting, J. T. Kuethe, G. X. Yang, T. Jian, J. Liu, D. Guiadeen, A. D. Krikorian, D. M. Sperbeck, L. M. Sonatore, J. Wiltsie, C. C. Chung, J. T. Gibson, J. M. Lisnock, B. A. Murphu, J. N. Gorski, J. Liu, D. Chen, X. Chen, M. Wolff, S. X. Tong, M. Madeira, B. V. Karanam, D.-M. Shen, J. M. Balcovec, S. Pinto, R. P. Nargund, and R. J. DeVita, ACS Med. Chem. Lett., 4, 773 (2013).

    Article  CAS  Google Scholar 

  52. F. Seela, W. Bourgeois, H. Rosemeyer, and T. Wenzel, Helv. Chim. Acta, 79, 488 (1996).

    Article  CAS  Google Scholar 

  53. J. Parsch and J. W. Engels, Helv. Chim. Acta., 83, 1791 (2000).

    Article  CAS  Google Scholar 

  54. R. Zou, J. C. Drach, and L. B. Townsend, J. Med. Chem., 40, 811 (1997).

    Article  CAS  Google Scholar 

  55. J. C. Drach, L. B. Townsend, F. L. Boyd, S. D. Chamberlain, S. M. Daluge, D. N. Deaton, M. W. Andersеn and G. A. Freeman, WO Pat. Appl. 9856761.

  56. A. E. Klöpffer and J. W. Engels, ChemBioChem, 5, 707 (2004).

    Article  Google Scholar 

  57. J. Haas and J. W. Engels, Tetrahedron Lett., 48, 8891 (2007).

    Article  CAS  Google Scholar 

  58. J. Parsch and J. W. Engels, Nucleosides, Nucleotides Nucleic Acids, 20, 815 (2001).

    Article  CAS  Google Scholar 

  59. A. E. Klöpffer and J. W. Engels, Nucleosides, Nucleotides Nucleic Acids, 24, 651 (2005).

    Article  Google Scholar 

  60. M. Hammad, A. Mequid, M. El. Ananni, and N. Shafic, Egypt. J. Chem., 29, 5401 (1987).

    Google Scholar 

  61. S. M. Rida, F. S. G. Soliman, E.-S. A. M. Badaway, and T. Kappe, J. Heterocycl. Chem., 25, 1725 (1988).

    Article  CAS  Google Scholar 

  62. E. Badaway and T. Kappe, Eur. J. Med. Chem., 30, 327 (1995).

    Article  Google Scholar 

  63. S. D. Chamberlain, S. M. Daluge, and G. W. Koszalka, US Pat. Appl. 5998605.

  64. L. B. Townsend, J. C. Drach, and G. A. Freeman, US Pat. Appl. 5840743.

  65. G. N. Lipunova, E. V. Nosova, G. A. Mokrushina, E. G. Ogloblina, G. G. Aleksandrov, and V. N. Charushin, Zh. Org. Khim., 39, 270 (2003). [Russ. J. Org. Chem. 39, 248 (2003).]

  66. S. K. Kotovskaya, Z. M. Baskakova, V. N. Charushin, O. N. Chupakhin, E. F. Belanov, N. I. Bormotov, S. M. Balakhnin, and O. A. Serov, Khim.-Farm. Zh., 39, No. 11, 12 (2005). [Pharm. Chem. J., 39, 574 (2005).]

  67. C. Hubschwerlen, P. Pflieger, J.-L. Specklin, K. Gubemator, H. Gmünder, P. Angehrn, and I. Kompis, J. Med. Chem., 35, 1385 (1992).

    Article  CAS  Google Scholar 

  68. G. N. Lipunova, G. A. Mokrushina, E. V. Nosova, L. I. Rusinova, and V. N. Charushin, Mendeleev Commun., 7, 109 (1997).

    Article  Google Scholar 

  69. E. V. Nosova, G. N. Lipunova, G. M. Mokrushina, O. M. Chasovskikh, L. I. Rusinova, and V. N. Charushin, Zh. Org. Khim., 34, 436 (1998). [Russ. J. Org. Chem., 34, 408 (1998).]

  70. E. V. Nosova, N. N. Mochul'skaya, S. K. Kotovskaya, G. N. Lipunova, and V. N. Charushin, Heteroat. Chem., 17, 579 (2006).

    Article  CAS  Google Scholar 

  71. V. N. Charushin, E. V. Nosova, G. N. Lipunova, and M. I. Kodess, J. Fluorine Chem., 110, 25 (2001).

    Article  CAS  Google Scholar 

  72. G. N. Lipunova, G. A. Mokrushina, E. V. Granovskaya, O. M. Chasovskikh, and V. N. Charushin, Mendeleev Commun., 6, 15 (1996).

    Article  Google Scholar 

  73. G. N. Lipunova, G. M. Mokrushina, E. V. Nosova, O. M. Chasovskikh, L. I. Rusinova, V. N. Charushin, and G. G. Aleksandrov, Zh. Org. Khim., 33, 1556 (1997). [Russ. J. Org. Chem. 33, 1476 (1997).]

  74. K. Wu and Q.-Y. Chen, Synthesis, 35 (2003).

  75. X. Fang, Y.-M. Wu, J. Deng, and S.-W. Wang, Tetrahedron, 60, 5487 (2004).

    Article  CAS  Google Scholar 

  76. A. G. Pokrovskii, T. N. Il'icheva, S. K. Kotovskaya, S. A. Romanova, V. N. Charushin, and O. N. Chupakhin, Dokl. Akad. Nauk, 398, 412 (2004). [Dokl. Biochem. Biophys., 398, 285 (2004).]

  77. C. Hubschwerlen, I. Kompis, and J.-L. Specklin, CА Pat. Appl. 2028530.

  78. G. N. Lipunova, E. V. Nosova, G. A. Mokrushina, L. P. Sidorova, and V. N. Charushin, Khim.-Farm. Zh., 34, No. 1, 20 (2000). [Pharm. Chem. J., 34, 19 (2000).]

  79. G. N. Lipunova, E. V. Nosova, L. P. Sidorova, and V. N. Charushin, Khim.-Farm. Zh., 45, No. 4, 12 (2011). [Pharm. Chem. J., 45, 208 (2011).]

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Authors and Affiliations

  1. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22. S. Kovaleskoi St. / 20 Akademicheskaya St., Yekaterinburg, 620219, Russia

    G. N. Lipunova & V. N. Charushin

  2. Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg, 620002, Russia

    G. N. Lipunova, E. V. Nosova & V. N. Charushin

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  1. G. N. Lipunova
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  2. E. V. Nosova
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  3. V. N. Charushin
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Correspondence to E. V. Nosova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 831-859, June, 2014.

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Lipunova, G.N., Nosova, E.V. & Charushin, V.N. Fluorine-Containing Benzimidazoles and Their [a]- and [b]Heteroannelated Derivatives: Synthesis and Biological Activity (Review). Chem Heterocycl Comp 50, 764–790 (2014). https://doi.org/10.1007/s10593-014-1533-0

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