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The newer synthetic strategies for DNA binding pyrrolobenzodiazepine antibiotics (review)

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Chemistry of Heterocyclic Compounds Aims and scope

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Modern synthetic approaches to DNA binding pyrrolobenzodiazepine antibiotics have been discussed.

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References

  1. D. E. Thurston, in: Molecular Aspects of Anticancer Drug DNA Interaction, S. Neidle and M. J. Waring (Eds.), Macmillan, Vol. 1 (1993), pp. 54–88.

  2. J. A. Hartley and R. L. Souhami, in: Cancer Chemotherapy; Frontiers in Pharmacology and Therapeutics, J. A. Hickman, T. Tritton (Eds.), Blackwell Scientific Ltd. (1993), pp. 251–280.

  3. W. A. Remers, in: The Chemistry of Antitumor Antibiotics, Wiley: New York, Vol. 2 (1998), pp. 28–92.

    Google Scholar 

  4. J. A. Mountzouris, L. H. Hurley, in: Advances in DNA Sequence-Selecitive Agents, Padwa, Ed., JAI Press: London, Vol. 1 (1992), pp. 263–292.

    Google Scholar 

  5. D. E. Thurston and L. H. Hurley, Drugs Future,8, 957 (1983).

    Google Scholar 

  6. L. H. Hurely and D. E. Thurston, Pharm. Res.,2, 52 (1984).

    Google Scholar 

  7. L. H. Hurely, T. Reck, D. E. Thurston, D. R. Langley, K. G. Holden, R. P. Hertzberg, J. R. E. Hoover, G. Gallagher, Jr., L. F. Faucette, S.-M. Mong, and R. K. Johnson, Chem. Res. Toxicol.,1, 258 (1998).

    Google Scholar 

  8. L. H. Hurley and R. L. Petrusek, Nature,282, 529 (1979).

    Article  CAS  Google Scholar 

  9. R. L. Petrusek, G. L. Anderson, T. F. Garner, Q. L. Fannin, D. J. Kaplan, S. G. Zimmer, and L. H. Hurely, Biochemistry,20, 1111 (1981).

    Article  CAS  Google Scholar 

  10. R. L. Petrusek, E. L. Uhlenhopp, N. Duteau, and L. H. Hurley, J. Biol. Chem.,257, 6207 (1982).

    CAS  Google Scholar 

  11. R. P. Hertzberg, S. M. Hecht, V. L. Reynolds, I. J. Molineux and L. H. Hurely, Biochemistry,25, 1249 (1986).

    Article  CAS  Google Scholar 

  12. F. L. Boyd, D. Stewart, W. A. Remers, M. D. Barkley, and L. H. Hurley, Biochemistry,32, 8712 (1993).

    Google Scholar 

  13. R. Kizu, P. H. Draves, and L. H. Hurley, Biochemistry,32, 8712 (1993).

    Article  CAS  Google Scholar 

  14. J. A. Hartley, J. P. Bingham, and R. L. Souhani, Nucleic Acids Res.,20, 3175 (1992).

    CAS  Google Scholar 

  15. M. Lee, A. L. Rhodes, M. D. Wyatt, S. Forrow, and J. A. Hartley, Anticancer Drug Design,8, 173 (1993).

    CAS  Google Scholar 

  16. D. S. Bose, A. S. Thompson, J. Ching, J. A. Hartley, M. Berardini, T. C. Jenkins, S. Neidle, L. H. Hurley, and D. E. Thurston, J. Am. Chem. Soc.,114, 4939 (1992).

    Article  CAS  Google Scholar 

  17. D. S. Bose, A. S. Thompson, M. Smellie, M. D. Berardini, J. A. Hartley, T. C. Jenkins, S. Neidle, and D. E. Thurston, J. Chem. Soc. Chem. Commun., No. 20, 1518 (1992).

    Google Scholar 

  18. T. C. Jenkins, S. Neidle, and D. E. Thurston, in: Chemistry of Heterocyclic Compounds, I. Stibor (Ed.), Prague Institute of Chemical Technology: Prague (1993), p. 173.

    Google Scholar 

  19. J.-J. Wan, G. C. Hill, and L. H. Hurley, J. Med. Chem.,35, 2995 (1992).

    Google Scholar 

  20. J. A. Mountzouris, J. J. Wang, D. E. Thurston, and L. H. Hurley, J. Med. Chem.,37, 3132 (1994).

    Article  CAS  Google Scholar 

  21. W. Leimgruber, A. D. Batcho, and R. C. Czajkowski, J. Am. Chem. Soc.,90, 5641 (1968).

    Article  CAS  Google Scholar 

  22. D. E. Thurston and D. S. Bose, Chem. Rev.,94, 433 (1994).

    Article  CAS  Google Scholar 

  23. T. Kaneko, H. Wong, and T. W. Doyl, Tetrahedron Lett.,24, 5165 (1983).

    Article  CAS  Google Scholar 

  24. J. W. Suggs, Y. S. Wang, and K. S. Lee, Tetrahedron Lett.,26, 4871 (1985).

    Article  CAS  Google Scholar 

  25. J. W. Lown and A. V. Joshua, Biochem. Pharmacol.,28, 2017 (1979).

    CAS  Google Scholar 

  26. N. Langlois, F. Favre, and A. Rojas, Tetrahedron Lett.,34, 4365 (1993).

    Google Scholar 

  27. T. Kaneko, H. Wong, T. W. Doyle, W. C. Rose, and W. T. Bradner, J. Med. Chem.,28, 388 (1985).

    CAS  Google Scholar 

  28. D. R. Langley and D. E. Thurston, J. Org. Chem.,52, 91 (1987).

    Article  CAS  Google Scholar 

  29. S. M. Courtney and D. E. Thurston, Tetrahedron Lett.,34, 5327 (1993).

    Article  CAS  Google Scholar 

  30. D. S. Bose, G. B. Jones, and D. E. Thurston, Tetrahedron,48, 751 (1992).

    Article  Google Scholar 

  31. M. Mori, M. Kimura, Y. Uozumi, and Y. Ban, Tetrahedron Lett.,26, 5947 (1985).

    CAS  Google Scholar 

  32. M. Mori, Y. Uozumi, and Y. Ban, J. Chem. Soc. Chem. Commun., No. 11, 841 (1986).

    Google Scholar 

  33. A. Kamal, B. S. P. Reddy, and B. S. N. Reddy, Tetrahedron Lett.,37, 2281 (1996).

    CAS  Google Scholar 

  34. M. Artico, G. De Martino, R. Giuliano, S. Massa, and G. C. Porretta, J. Chem. Soc. Chem. Commun., No. 12, 671 (1969).

    Google Scholar 

  35. M. Miyamoto, S. Kondo, H. Naganawa, K. Maeda, M. Ohno, and H. Umezawa, J. Antibiot.,50, 340 (1997).

    Google Scholar 

  36. Z. Tozuka, H. Takasugi, and T. Takaya, J. Antibiot.,36, 276 (1983).

    CAS  Google Scholar 

  37. D. E. Thurston and D. R. Langley, J. Org. Chem.,51, 705 (1986).

    Article  CAS  Google Scholar 

  38. A. Kamal, B. S. P. Reddy, and B. S. N. Reddy, Tetrahedron Lett.,37, 2281 (1996).

    CAS  Google Scholar 

  39. D. R. Langley and D. E. Thurston, J. Org. Chem.,52, 91 (1987).

    Article  CAS  Google Scholar 

  40. S. Eguchi, K. Yamashita, Y. Matsushita, and A. Kakehi, J. Org. Chem.,60, 4006 (1995).

    Article  CAS  Google Scholar 

  41. P. Molina, I. Diaz, and A. Tarraga, Tetrahedron,51, 5617 (1995).

    CAS  Google Scholar 

  42. A. Kamal, N. V. Rao, and E. Laxman, Tetrahedron Lett.,38, 6945 (1997).

    CAS  Google Scholar 

  43. I. A. O'Neil, C. L. Murray, R. C. Hunter, S. B. Kalindjian, and T. C. Jenkins, Synlett., No. 1, 75 (1997).

    Google Scholar 

  44. A. Kamal, B. S. P. Reddy, and B. S. N. Reddy, Tetrahedron Lett.,37, 6803 (1996).

    CAS  Google Scholar 

  45. K. R. Prabhu, P. S. Sivanand, and S. Chandrasekaran, Synlett, No. 1, 47 (1988).

    Google Scholar 

  46. P. H. Mazzocchi and A. D. Schuda, Heterocycles,23, 1603 (1985).

    CAS  Google Scholar 

  47. D. E. Thurston, G. B. Jones, and M. E. Davies, J. Chem. Soc. Chem. Commun., No. 15, 874 (1990).

    Google Scholar 

  48. S. Mori, T. Aoyama, and T. Shion, Tetrahedron Lett.,27, 6111 (1986).

    CAS  Google Scholar 

  49. D. E. Thurston, P. T. P. Kaumaya, and L. H. Hurley, Tetrahedron Lett.,25, 4706 (1984).

    Article  Google Scholar 

  50. J. D. Farmer, G. R. Gustafson, Jr., A. Conti, M. B. Zimmt, and J. W. Suggs, Nucleic Acids Res.,19, 899 (1991).

    CAS  Google Scholar 

  51. J. D. Farmer, S. M. Rudnick, Jr., and J. W. Suggs, Tetrahedron Lett.,29, 5105 (1988).

    Article  CAS  Google Scholar 

  52. J. D. Farmer, Jr., Ph. D. Thesis, Brown University (1989).

  53. I. D. Zhang and J. W. Suggs, Abstracts of Papers of American Chemical Society,204, 112 (1992).

    Google Scholar 

  54. D. S. Bose, A. S. Thompson, J. A. Ching, J. A. Hartley, M. D. Beradini, T. C. Jenkins, S. Neidle, L. H. Hurley, and D. E. Thurston, J. Am. Chem. Soc.,114, 4934 (1992).

    Article  Google Scholar 

  55. D. E. Thurston and D. S. Bose, PCT WO 93 1845; Chem. Abstr.,120, 270468 (1994).

    Google Scholar 

  56. J. A. Mountzouris, J. J. Wang, D. E. Thurston, and L. H. Hurley, J. Med. Chem.,37, 3132 (1984).

    Google Scholar 

  57. T. C. Jenkins., L. H. Hurley, S. Neidle, and D. E. Thurston, J. Med. Chem.,37, 4529 (1994).

    Article  CAS  Google Scholar 

  58. D. E. Thurston, D. S. Bose, A. S. Thompson, P. W. Howard, A. Leoni, S. J. Croker, T. C. Jenkins, S. Neidle, J. A. Hartley, and L. H. Hurley, J. Org. Chem.,61, 8141 (1996).

    Article  CAS  Google Scholar 

  59. A. Kamal and N. V. Rao, Tetrahedron Lett.,36, 4299 (1995).

    Article  CAS  Google Scholar 

  60. D. E. Thurston, S. J. Morris and J. A. Hartley, J. Chem. Soc. Chem. Commun., No. 4, 563 (1996).

    Google Scholar 

  61. S. C. Willson, P. W. Howard, and D. E. Thurston, Tetrahedron Lett.,36, 6333 (1995).

    Google Scholar 

  62. A. Kamal, Y. Damayanthi, B. S. N. Reddy, B. Lakminaryana, and B. S. P. Reddy, J. Chem. Soc. Chem. Commun., No. 11, 1015 (1997).

    Google Scholar 

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Biotransformation Laboratory, Division of Organic Chemistry I, Indian Institute of Chemical Technology, Hyderabad 500007, India. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1588–1604, December, 1998.

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Kamal, A., Rao, M.V. & Satyanarayana Reddy, B. The newer synthetic strategies for DNA binding pyrrolobenzodiazepine antibiotics (review). Chem Heterocycl Compd 34, 1342–1358 (1998). https://doi.org/10.1007/BF02317805

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  • DOI: https://doi.org/10.1007/BF02317805

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