Iminosugar C-Glycosides: Synthesis and Biological Activity

Iminosugars: From Synthesis to Therapeutic Applications

Volumn , Issue , 2008, Pages 63-86

  Compain, Philippe ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

Activated sugar donors; Carbohydrate processing enzyme inhibitors; Chemical chaperone therapy; Dicarbonyl sugars reductive amination; Digestive glucosidases inhibition; Endocyclic nitrogen; Glycoenzyme and glycosidase inhibitors; Iminosugar based drug; Iminosugar derived nitrone; Potential medicinal applications

Indexed keywords

EID: 84889293904     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470517437.ch4     Document Type: Chapter

References (98)

1. Mitrakou, A., Tountas, N., Raptis, A. E., Bauer, R. J., Schulz, H. and Raptis, S. A., 1998 Diab. Med., 15, 657-660.
2. Scott, L. J. and Spencer, C. M., 2000 Drugs, 59, 521-549.
3. Stütz, A. E. (ed.), 1999 Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond. Wiley-VCH, New York.
4. Asano, N., Nash, R. J., Molyneux, R. J. and Fleet, G. W. J., 2000 Tetrahedron: Asymmetry, 11, 1645-1680.
5. Compain, P. and Martin, O. R., 2001 Bioorg. Med. Chem., 9, 3077-3092.
6. Compain, P. and Martin, O. R., 2003 Curr. Top. Med. Chem., 3, 541-560.
7. Moriyama, H., Tsukida, T., Inoue, Y., Yokota, K., Yoshino, K., Kondo, H., Miura, N. and Nishimura, S.-I., 2004 J. Med. Chem., 47, 1930-1938.
8. Schramm, V. L. and Tyler, P. C. 2003 Curr. Top. Med. Chem., 3, 525-540.
9. Lee, R. E., Smith, M. D., Pickering, L. and Fleet, G. W. J., 1999 Tetrahedron Lett., 40, 8689-8692.
10. Lee, R. E., Smith, M. D., Nash, R. J., Griffiths, R. C., McNeil, M., Grewal, R. K., Yan, W., Besra, G. S., Brennan, P. J. and Fleet, G. W. J., 1997 Tetrahedron Lett., 38, 6733-6736.
11. Martin, O. R. and Compain, P. (eds), 2003 Iminosugars: recent insights into their bioactivity and potential as therapeutic agents, in Curr. Top. Med. Chem., Bentham, Hilversum, Netherlands, Volume 3, issue 5, pp. 471-591.
12. Alper, J., 2001 Science, 291, 2338-2343.
13. Martin, O. R., 1997 In Carbohydrate Mimics: Concepts and Methods (Y. Chapleur (ed.), Wiley-VCH, pp. 259-282.
14. Zou, W., 2005 Curr. Top. Med. Chem., 5, 1363-1391.
15. Liu, P. S., 1987 J. Org. Chem., 52, 4717-4721.
16. For recent reviews devoted to the synthesis of iminosugars: (a) Cipolla, L., La Ferla, B. and Nicotra, F., 2003 Curr. Top. Med. Chem., 3, 485-511.
17. Pearson, M. S. M., Mathé-Allainmat, M., Fargeas, V. and Lebreton, J., 2005 Eur. J. Org. Chem., 11, 2159-2191.
18. Dhavale, D. D. and Matin, M. M., 2005 Arkivoc, 110-132.
19. Afarinkia, K. and Bahar, A., 2005 Tetrahedron: Asymmetry, 16, 1239-1287.
20. La Ferla, B. and Nicotra, F., 1999 In Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond, (A. E. Stütz, ed.). Wiley-VCH, New York, pp. 68-92.
21. Robina, I. and Vogel, P., 2005 Synthesis, 675-702.
22. Two chapters devoted to the general synthesis of iminosugars and imino-C-disaccharides are included in this book: Chapters 3 and 5.
23. Postema, M. H. D., 1995 C-Glycoside Synthesis. CRC Press: Boca Raton.
24. Du, Y., Linhardt, R. J. and Vlahov, I. R., 1998 Tetrahedron, 54, 9913-9959.
25. Xie, J., 1999 Recent Res. Devel. Organic Chem., 3, 505-523.
26. Lee, D. Y. W. and He, M., 2005 Curr. Top. Med. Chem., 5, 1333-1350.
27. Godin, G., Compain, P., Masson, G. and Martin, O. R., 2002 J. Org. Chem., 67, 6960-6970.
28. Masson, G., Compain, P. and Martin, O. R., 2000 Org. Lett., 2, 2971-2974.
29. Godin, G., Compain, P. and Martin, O. R., 2003 Org. Lett., 5, 3269-3272.
30. Godin, G., Compain, P. and Martin, O. R., 2003 Synlett, 2065-2067.
31. Cipolla, L., La Ferla, B., Peri, F. and Nicotra, F., 2000 Chem. Commun., 1289-1290.
32. Cipolla, L., Palma, A., La Ferla, B. and Nicotra, F., 2002 J. Chem. Soc., Perkin Trans I, 2161-2165.
33. Saavedra, O. M. and Martin, O. R., 1996 J. Org. Chem., 61, 6987-6993.
34. Leeuwenburgh, M. A., Picasso, S., Overkleeft, H. S., Van der Marel, G. A., Vogel, P. and Van Boom, J. H., 1999 Eur. J. Org. Chem., 1185-1189.
35. Cheng, X., Kumaran, G. and Mootoo, D. R., 2001 Chem. Commun., 811-812.
36. Johnson, C. R., Miller, M. W., Golebiowski, A., Sundram, H. and Ksebati, M. B., 1994 Tetrahedron Lett., 35, 8991-8994.
37. Johns, B. A., Pan, Y. T., Elbein, A. D. and Johnson, C. R., 1997 J. Am. Chem. Soc., 119, 4856-4865.
38. Johns, B. A. and Johnson, C. R., 1998 Tetrahedron Lett., 39, 749-752.
39. La Ferla, B., Bugada, P., Cipolla, L., Peri, F. and Nicotra, F., 2004 Eur. J. Org. Chem., 2451-2470.
40. Fleet, G. W. J., Namgoong, S. K., Barker, C., Baines, S., Jacob, G. S. and Winchester, B., 1989 Tetrahedron Lett., 30, 4439-4442.
41. Shilvock, J. P., Nash, R. J., Watson, A. A., Winters, A. L., Butters, T. D., Dwek, R. A., Winkler, D. A. and Fleet, G. W. J., 1999 J. Chem. Soc., Perkin Trans I, 2747-2754.
42. Mitchell, M., Qaio, L. and Wong, C.-H., 2001 Adv. Synth. Catal., 343, 596-599.
43. Straub, A., Effenberger, F. and Fischer, P., 1990 J. Org. Chem., 55, 3926-3932.
44. Baudat, A., Picasso, S. and Vogel, P., 1996 Carbohydrate Res., 281, 277-284.
45. Dondoni, A. and Perrone, D., 2003 Tetrahedron, 59, 4261-4273.
46. For a related synthetic strategy see: Cipolla, L., Lay, L., Nicotra, F., Pangrazio, C. and Panza, L., 1995 Tetrahedron, 51, 4679-4690.
47. Bruce, I., Fleet, G.W.J., Cenci di Bello, I.andWinchester, B., 1992 Tetrahedron, 48, 10191-10200.
48. Pino-Gonzalez, M. S., Assiego, C. and Lopez-Herrera, F. J., 2003 Tetrahedron Lett., 44, 8353-8356.
49. Martin, O. R., Liu, L. and Yang, F., 1996 Tetrahedron Lett., 37, 1991-1994.
50. Martin, O. R., Saavedra, O. M., Xie, F., Liu, L., Picasso, S., Vogel, P., Kizu, H. and Asano, N., 2001 Bioorg. Med. Chem., 9, 1269-1278.
51. Goujon, J.-Y., Gueyrard, D., Compain, P., Martin, O. R., Ikeda, K., Kato, A. and Asano, N., 2005 Bioorg. Med. Chem., 13, 2313-2324.
52. Liotta, L. J., Lee, J. and Ganem, B., 1991 Tetrahedron, 47, 2433-2447.
53. Yi, T., Wu, A.-A., S.-H and Zou, W., 2005 Tetrahedron, 61, 11716-11722.
54. McAlpine, I. J. and Armstrong, R. W., 2000 Tetrahedron Lett., 41, 1849-1853.
55. Bruce, I., Fleet, G. W. J., Cenci di Bello, I. and Winchester, B., 1989 Tetrahedron Lett., 30, 7257-7260.
56. Shilvock, J. P., Hsia, K. Y., Nash, R. J., Lloyd, J. D., Winters, A. L., Asano, N. and Fleet, G. W. J., 1998 Tetrahedron: Asymmetry, 9, 4157-4164.
57. Böshagen, H., Geiger, W. and Junge, B., 1981 Angew. Chem. Int. Ed. Engl., 20, 806-807.
58. Wong, C.-H., Provencher, L., Porco, J. A., Jung, S.-H., Wang, Y.-F., Chen, L., Wang, R. and Steensma, D. H., 1995 J. Org. Chem., 60, 1492-1501.
59. Anzeveno, P. B., Creemer, L. J., Daniel, J. K., King, C.-H. R. and Liu, P. S., 1989 J. Org. Chem., 54, 2539-2542.
60. Fuchss, T., Streicher, H. and Schmidt, R. R., 1997 Liebigs Ann./Recueil, 1315-1321.
61. Johnson, C. R., Golebiowski, A., Sundram, H., Miller, M. W. and Dwaihy, R. L., 1995 Tetrahedron Lett., 36, 653-654.
62. Granier, T. and Vasella, A., 1998 Helv. Chim. Acta, 81, 865-880.
63. Ojima, I. and Vidal, E. S., 1998 J. Org. Chem., 63, 7999-8003.
64. Shankar, B. B., Kirkup, M. P., McCombie, S. W. and Ganguly, A. K., 1993 Tetrahedron Lett., 34, 7171-7174.
65. Adelbrecht, J.-C., Craig, D., Dymock, B. W. and Thorimbert, S., 2000 Synlett, 467-470.
66. Maughan, M. A. T., Davies, I. G., Claridge, T. D. W., Courtney, S., Hay, P. and Davis, B. G., 2003 Angew. Chem. Int. Ed. Engl., 42, 3788-3792.
67. Timmer, M. S. M., Risseeuw, M. D. P., Verdoes, M., Filippov, D. V., Plaisier, J. R., Van der Marel, G. A., Overkleeft, H. S. and Van Boom, J. H., 2005 Tetrahedron: Asymmetry, 16, 177-185.
68. Peer, A. and Vasella, A., 1999 Helv. Chim. Acta, 82, 1044-1065.
69. Takayama, S., Martin, R., Wu, J., Laslo, K., Siuzdak, G. and Wong, C.-H., 1997 J. Am. Chem. Soc., 119, 8146-8151.
70. Dransfield, P. J., Gore, P. M., Shipman, M. and Slawin, A. M. Z., 2002 Chem. Commun., 150-151.
71. Dransfield, P. J., Gore, P. M., Prokes, I., Shipman, M. and Slawin, A. M. Z., 2003 Org. Biomol. Chem., 1, 2723-2733.
72. Duff, F. J., Vivien, V. and Wightman, R. H., 2000 Chem. Commun., 2127-2128.
73. Tailor, J. and Hall, D. G., 2000 Org Lett., 2, 3715-3718.
74. Shürer, S. C. and Blechert, S., 1999 Tetrahedron Lett., 40, 1877-1880.
75. Dondoni, A., Giovannini, P. P. and Perrone, D., 2005 J. Org. Chem., 70, 5508-5518.
76. Godin, G., Compain, P., Martin, O. R., Ikeda, K., Yu, L. and Asano, N., 2004 Bioorg. Med. Chem. Lett., 14, 5991-5995.
77. Chang, C.-F., Ho, C.-W., Wu, C.-Y., Chao, T.-A., Wong, C.-H. and Lin, C.-H., 2004 Chem. Biol., 11, 1301-1306.
78. Wu, C.-Y., Chang, C.-F., Chen, J. S.-Y., Wong, C.-H. and Lin, C.-H., 2003 Angew. Chem. Int. Ed. Engl., 42, 4661-4664.
79. Ho, C.-W., Lin, Y.-N., Chang, C.-F., Li, S.-T., Wu, Y.-T., Wu, C.-Y., Chang, C.-F., Liu, S.-W., Li, Y.-K. and Lin, C.-H., 2006 Biochemistry, 45, 5695-5702.
80. Schuster, M. and Blechert, S., 2001 Bioorg. Med. Chem. Lett., 11, 1809-1811.
81. Mitchell, M. L., Tian, F., Lee, L. V. and Wong, C.-H., 2002 Angew. Chem. Int. Ed. Engl., 41, 3041-3044.
82. Mitchell, M. L., Lee, L. V. and Wong, C.-H., 2002 Tetrahedron Lett., 43, 5691-5693.
83. Murray, B. W., Wittmann, V., Burkart, M. D., Hung, S.-S. and Wong, C.-H., 1997 Biochemistry, 36, 823-831.
84. Lee, L. V., Mitchell, M. L., Huang, S.-J., Fokin, V. V., Sharpless, B. and Wong, C.-H., 2003 J. Am. Chem. Soc., 125, 9588-9589.
85. Weber, K. T., Hammache, D., Fantini, J. and Ganem B., 2000 Bioorg. Med. Chem. Lett., 10, 1011-1014.
86. Augustin, L. A., Fantini, J. and Mootoo, D. R., 2006 Bioorg. Med. Chem., 10, 1182-1188.
87. Butters, T. D., Dwek, R. A. and Platt, F. M., 2003 Curr. Top. Med. Chem., 3, 561-574.
88. Futerman, A. H., Sussman, J. L., Horowitz, M., Silman, I. and Zimran, A., 2004 Trends Pharm. Sci., 25, 147-151.
89. Fan, J.-Q., 2003 Trends Pharm. Sci., 24, 355-360.
90. Sawkar, A. R., Cheng, W.-C., Beutler, E., Wong, C.-H., Balch, W. E. and Kelly, J. W., 2002 Proc. Natl. Acad. Sci USA, 99, 15428-15433.
91. Compain, P., Martin, O. R., Boucheron, C., Godin, G., Yu, L., Ikeda, K. and Asano, N., 2006 ChemBioChem, 7, 1356-1359.
92. Yu, L., Ikeda, K., Kato, A., Adachi, I., Godin, G., Compain, P., Martin, O. R. Asano, N., 2006 Bioorg. Med. Chem., 14, 7736-7744.
93. Asano, N., Ishii, S., Kizu, H., Yasuda, K., Martin, O. R. and Fan J.-Q., 2000 Eur. J. Biochem., 267, 4179-4186.
94. Boucheron, C., Desvergnes, V., Compain, P., Martin, O. R., Lavi, A., Mackeen, M., Wormald, M. R., Dwek, R. A. and Butters, T. D., 2005 Tetrahedron: Asymmetry, 16, 1747-1756.
95. Godin, G., Compain, P., Martin, O. R., Lavi, A. and Butters, T. D., unpublished results.
96. See, for example,: (a) Liu, L. and Postema, M. H. D., 2001 J. Am. Chem. Soc., 123, 8602-8603.
97. Postema, M. H. D. and Piper, J. L., 2003 Org. Lett., 5, 1721-1723.
98. Ikeda, K., Takahashi, M., Nishida, M., Miyauchi, M., Kizu, H., Kameda, Y., Arisawa, M., Watson, A. A., Nash, R. J., Fleet, G. W. J. and Asano, N., 2000 Carbohydr. Res., 323, 73-80.