A new access to polyhydroxy piperidines of the azasugar class: Synthesis and glycosidase inhibition studies

Organic and Biomolecular Chemistry

Volumn 1, Issue 19, 2003, Pages 3321-3326

  Pandey, Ganesh ^a   Kapur, Manmohan ^a   Islam Khan, M ^a   Gaikwad, Sushama M ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYMES; POSITIVE IONS; QUENCHING; SYNTHESIS (CHEMICAL);

INHIBITORS;

ORGANIC COMPOUNDS;

EID: 0142031005     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b307455b     Document Type: Article

References (51)

1. (a) B. Ganem, Acc. Chem. Res., 1996, 29, 340;
2. (b) A. de Raadt, C. W Ekhart, M. Ebner and A. E. Stütz, Top. Curr. Chem., 1997, 187, 157;
3. (c) A. E. Stütz, Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond, Wiley-VCH, Weinheim, Germany, 1999;
4. (d) V. H. Lillelund, H. H. Jensen, X. Laing and M. Bols, Chem. Rev., 2002, 102, 515 and references therein;
5. (e) Y. Ichikawa, Y. Igarashi, M. Ichikawa and Y. Suhara, J. Am. Chem. Soc., 1998, 120, 3007.
6. N. Asano, R. J. Nash, R. J. Molyneux and G. W. J. Fleet, Tetrahedron: Asymmetry, 2000, 11, 1645.
7. For some reviews on this topic see: (a) D. L, Zechel and S. G. Withers, Acc. Chem. Res., 2000, 33, 11; (b) P. Sears and C.-H. Wong, Angew. Chem., Int. Ed., 1999, 38, 2300; (c) T. D. Heightman and A. T. Vasella, Angew. Chem., Int. Ed., 1999, 38, 7.50.
8. For some reviews on this topic see: (a) D. L, Zechel and S. G. Withers, Acc. Chem. Res., 2000, 33, 11; (b) P. Sears and C.-H. Wong, Angew. Chem., Int. Ed., 1999, 38, 2300; (c) T. D. Heightman and A. T. Vasella, Angew. Chem., Int. Ed., 1999, 38, 7.50.
9. For some reviews on this topic see: (a) D. L, Zechel and S. G. Withers, Acc. Chem. Res., 2000, 33, 11; (b) P. Sears and C.-H. Wong, Angew. Chem., Int. Ed., 1999, 38, 2300; (c) T. D. Heightman and A. T. Vasella, Angew. Chem., Int. Ed., 1999, 38, 7.50.
10. (a) T. M. Jespersen, W. Dong, M. R, Sierks, T. Skrydstrup, I. Lundt and M. Bols, Angew. Chem., Int. Ed. Engl, 1994, 33, 1778;
11. (b) A. Hansen, T. M. Tagmose and M. Bols, Chem. Commun., 1996, 2649;
12. (c) M. Bols, R. G. Hazell and Ib B. Thomsen, Chem. Eur. J., 1997, 3, 940;
13. (d) H. Liu, X. Liang, H. H. Søhoel, A. Bülow and M. Bols, J. Am. Chem. Soc., 2001, 123, 5116;
14. (e) H. Søhoel, X. Liang and M. Bols, J. Chem. Soc., Perkin Trans, 1, 2001, 1584.
15. See ref. 1(e) and (a) Y. Igarashi, M. Ichikawa and Y. Ichikawa, Bioorg. Med. Chem. Lett., 1996, 6, 553; (b) Y. Ichikawa and Y. Igarashi, Tetrahedron Lett., 1995, 36, 4585; (c) M. Ichikawa, Y. Igarashi and Y. Ichikawa, Tetrahedron Lett., 1995, 36, 1767; (d) Y. Igarashi, M. Ichikawa and Y. Ichikawa, Tetrahedron Lett., 1996, 37, 2707.
16. See ref. 1(e) and (a) Y. Igarashi, M. Ichikawa and Y. Ichikawa, Bioorg. Med. Chem. Lett., 1996, 6, 553; (b) Y. Ichikawa and Y. Igarashi, Tetrahedron Lett., 1995, 36, 4585; (c) M. Ichikawa, Y. Igarashi and Y. Ichikawa, Tetrahedron Lett., 1995, 36, 1767; (d) Y. Igarashi, M. Ichikawa and Y. Ichikawa, Tetrahedron Lett., 1996, 37, 2707.
17. See ref. 1(e) and (a) Y. Igarashi, M. Ichikawa and Y. Ichikawa, Bioorg. Med. Chem. Lett., 1996, 6, 553; (b) Y. Ichikawa and Y. Igarashi, Tetrahedron Lett., 1995, 36, 4585; (c) M. Ichikawa, Y. Igarashi and Y. Ichikawa, Tetrahedron Lett., 1995, 36, 1767; (d) Y. Igarashi, M. Ichikawa and Y. Ichikawa, Tetrahedron Lett., 1996, 37, 2707.
18. See ref. 1(e) and (a) Y. Igarashi, M. Ichikawa and Y. Ichikawa, Bioorg. Med. Chem. Lett., 1996, 6, 553; (b) Y. Ichikawa and Y. Igarashi, Tetrahedron Lett., 1995, 36, 4585; (c) M. Ichikawa, Y. Igarashi and Y. Ichikawa, Tetrahedron Lett., 1995, 36, 1767; (d) Y. Igarashi, M. Ichikawa and Y. Ichikawa, Tetrahedron Lett., 1996, 37, 2707.
19. (a) Y. Nishimura, T. Kudo, S. Kondo and T. Takeuchi, J. Antibiot., 1994, 47, 101;
20. (b) Y. Nishimura, Studies in Natural Products Chemistry, ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1995, vol 16, p 75;
21. (c) Y. Nishimura, T. Satoh, T. Kudo, S. Kondo and T. Takeuchi, Bio Med. Chem., 1996, 4, 91;
22. (d) Y. Nishimura, E. Shitara, H. Adachi, M. Toyoshima, M. Nakajima, Y. Okami and T. Takeuchi, J. Org. Chem., 2000, 65, 2;
23. E. Shitara, Y. Nishimura, F. Kojima and T. Takeuchi, Bioorg. Med. Chem., 2000, 8, 343.
24. R. C. Bernotas, G. Papandreou, J. Urbach and B. Ganem, Tetrahedron Lett., 1990, 31, 3393.
25. T. Sekioka, M. Shibano and G. Kusano, Nat. Med., 1995, 49, 332.
26. For 1-N-iminosugar syntheses see refs 4-6 and (a) G. Guanti and R. Riva, Tetrahedron Lett., 2003, 44, 357; (b) J. Andersch and M. Bols, Chem. Eur. J., 2001, 7, 2744; (c) G. Zhao, U. C. Deo and B. Ganem, Org. Lett., 2001, 3, 201; (d) Y. J. Kim, M. Ichikawa and Y. Ichikawa, J. Org. Chem., 2000, 65, 2599; (e) G. Mehta and N. Mohal, Tetrahedron Lett., 2000, 41, 5747; (f) U. Kazmaier and C. Schneider, Tetrahedron Lett., 1998, 39, 817; (g) X. Liang, A. Lohse and M. Bols, J. Org. Chem., 2000, 65, 7432; (h) M. Bols, Tetrahedron Lett., 1996, 37, 2097.
27. For 1-N-iminosugar syntheses see refs 4-6 and (a) G. Guanti and R. Riva, Tetrahedron Lett., 2003, 44, 357; (b) J. Andersch and M. Bols, Chem. Eur. J., 2001, 7, 2744; (c) G. Zhao, U. C. Deo and B. Ganem, Org. Lett., 2001, 3, 201; (d) Y. J. Kim, M. Ichikawa and Y. Ichikawa, J. Org. Chem., 2000, 65, 2599; (e) G. Mehta and N. Mohal, Tetrahedron Lett., 2000, 41, 5747; (f) U. Kazmaier and C. Schneider, Tetrahedron Lett., 1998, 39, 817; (g) X. Liang, A. Lohse and M. Bols, J. Org. Chem., 2000, 65, 7432; (h) M. Bols, Tetrahedron Lett., 1996, 37, 2097.
28. For 1-N-iminosugar syntheses see refs 4-6 and (a) G. Guanti and R. Riva, Tetrahedron Lett., 2003, 44, 357; (b) J. Andersch and M. Bols, Chem. Eur. J., 2001, 7, 2744; (c) G. Zhao, U. C. Deo and B. Ganem, Org. Lett., 2001, 3, 201; (d) Y. J. Kim, M. Ichikawa and Y. Ichikawa, J. Org. Chem., 2000, 65, 2599; (e) G. Mehta and N. Mohal, Tetrahedron Lett., 2000, 41, 5747; (f) U. Kazmaier and C. Schneider, Tetrahedron Lett., 1998, 39, 817; (g) X. Liang, A. Lohse and M. Bols, J. Org. Chem., 2000, 65, 7432; (h) M. Bols, Tetrahedron Lett., 1996, 37, 2097.
29. For 1-N-iminosugar syntheses see refs 4-6 and (a) G. Guanti and R. Riva, Tetrahedron Lett., 2003, 44, 357; (b) J. Andersch and M. Bols, Chem. Eur. J., 2001, 7, 2744; (c) G. Zhao, U. C. Deo and B. Ganem, Org. Lett., 2001, 3, 201; (d) Y. J. Kim, M. Ichikawa and Y. Ichikawa, J. Org. Chem., 2000, 65, 2599; (e) G. Mehta and N. Mohal, Tetrahedron Lett., 2000, 41, 5747; (f) U. Kazmaier and C. Schneider, Tetrahedron Lett., 1998, 39, 817; (g) X. Liang, A. Lohse and M. Bols, J. Org. Chem., 2000, 65, 7432; (h) M. Bols, Tetrahedron Lett., 1996, 37, 2097.
30. For 1-N-iminosugar syntheses see refs 4-6 and (a) G. Guanti and R. Riva, Tetrahedron Lett., 2003, 44, 357; (b) J. Andersch and M. Bols, Chem. Eur. J., 2001, 7, 2744; (c) G. Zhao, U. C. Deo and B. Ganem, Org. Lett., 2001, 3, 201; (d) Y. J. Kim, M. Ichikawa and Y. Ichikawa, J. Org. Chem., 2000, 65, 2599; (e) G. Mehta and N. Mohal, Tetrahedron Lett., 2000, 41, 5747; (f) U. Kazmaier and C. Schneider, Tetrahedron Lett., 1998, 39, 817; (g) X. Liang, A. Lohse and M. Bols, J. Org. Chem., 2000, 65, 7432; (h) M. Bols, Tetrahedron Lett., 1996, 37, 2097.
31. For 1-N-iminosugar syntheses see refs 4-6 and (a) G. Guanti and R. Riva, Tetrahedron Lett., 2003, 44, 357; (b) J. Andersch and M. Bols, Chem. Eur. J., 2001, 7, 2744; (c) G. Zhao, U. C. Deo and B. Ganem, Org. Lett., 2001, 3, 201; (d) Y. J. Kim, M. Ichikawa and Y. Ichikawa, J. Org. Chem., 2000, 65, 2599; (e) G. Mehta and N. Mohal, Tetrahedron Lett., 2000, 41, 5747; (f) U. Kazmaier and C. Schneider, Tetrahedron Lett., 1998, 39, 817; (g) X. Liang, A. Lohse and M. Bols, J. Org. Chem., 2000, 65, 7432; (h) M. Bols, Tetrahedron Lett., 1996, 37, 2097.
32. For 1-N-iminosugar syntheses see refs 4-6 and (a) G. Guanti and R. Riva, Tetrahedron Lett., 2003, 44, 357; (b) J. Andersch and M. Bols, Chem. Eur. J., 2001, 7, 2744; (c) G. Zhao, U. C. Deo and B. Ganem, Org. Lett., 2001, 3, 201; (d) Y. J. Kim, M. Ichikawa and Y. Ichikawa, J. Org. Chem., 2000, 65, 2599; (e) G. Mehta and N. Mohal, Tetrahedron Lett., 2000, 41, 5747; (f) U. Kazmaier and C. Schneider, Tetrahedron Lett., 1998, 39, 817; (g) X. Liang, A. Lohse and M. Bols, J. Org. Chem., 2000, 65, 7432; (h) M. Bols, Tetrahedron Lett., 1996, 37, 2097.
33. For 1-N-iminosugar syntheses see refs 4-6 and (a) G. Guanti and R. Riva, Tetrahedron Lett., 2003, 44, 357; (b) J. Andersch and M. Bols, Chem. Eur. J., 2001, 7, 2744; (c) G. Zhao, U. C. Deo and B. Ganem, Org. Lett., 2001, 3, 201; (d) Y. J. Kim, M. Ichikawa and Y. Ichikawa, J. Org. Chem., 2000, 65, 2599; (e) G. Mehta and N. Mohal, Tetrahedron Lett., 2000, 41, 5747; (f) U. Kazmaier and C. Schneider, Tetrahedron Lett., 1998, 39, 817; (g) X. Liang, A. Lohse and M. Bols, J. Org. Chem., 2000, 65, 7432; (h) M. Bols, Tetrahedron Lett., 1996, 37, 2097.
34. For 3,4,5-piperidine triol syntheses, see refs 5(a), 7 and (a) H. Han, Tetrahedron Lett., 2003, 44, 1567; (b) N. T. Patil, S. John, S. G. Sabharwal and D. D. Dhawale, Bioorg. Med. Chem., 2002, 10, 2155; (c) M. Amat, N. Llor, M. Huguet, E. Molins, E. Espinosa and J. Bosch, Org. Lett., 2001, 3, 3257; (d) K. C. Jang, I.-Y. Jeong, M. S. Yang, S. U. Choi and K. H. Park, Heterocycles, 2000, 53, 887; (e) M. Godskesen, I. Lundt, R. Madsen and B. Winchester, Bioorg. Med. Chem., 1996, 4, 1857; (f) G. Legier, A. E. Stütz and H. Immich, Carbohydr. Res., 1995, 272, 17; (g) D. Sames and R.Polt, Synlett, 1995, 552; (h) T. Tschamber, F. Backenstrass, M. Neuberger, M. Zhender and J. Streith, Tetrahedron, 1994, 50, 1135.
35. For 3,4,5-piperidine triol syntheses, see refs 5(a), 7 and (a) H. Han, Tetrahedron Lett., 2003, 44, 1567; (b) N. T. Patil, S. John, S. G. Sabharwal and D. D. Dhawale, Bioorg. Med. Chem., 2002, 10, 2155; (c) M. Amat, N. Llor, M. Huguet, E. Molins, E. Espinosa and J. Bosch, Org. Lett., 2001, 3, 3257; (d) K. C. Jang, I.-Y. Jeong, M. S. Yang, S. U. Choi and K. H. Park, Heterocycles, 2000, 53, 887; (e) M. Godskesen, I. Lundt, R. Madsen and B. Winchester, Bioorg. Med. Chem., 1996, 4, 1857; (f) G. Legier, A. E. Stütz and H. Immich, Carbohydr. Res., 1995, 272, 17; (g) D. Sames and R.Polt, Synlett, 1995, 552; (h) T. Tschamber, F. Backenstrass, M. Neuberger, M. Zhender and J. Streith, Tetrahedron, 1994, 50, 1135.
36. For 3,4,5-piperidine triol syntheses, see refs 5(a), 7 and (a) H. Han, Tetrahedron Lett., 2003, 44, 1567; (b) N. T. Patil, S. John, S. G. Sabharwal and D. D. Dhawale, Bioorg. Med. Chem., 2002, 10, 2155; (c) M. Amat, N. Llor, M. Huguet, E. Molins, E. Espinosa and J. Bosch, Org. Lett., 2001, 3, 3257; (d) K. C. Jang, I.-Y. Jeong, M. S. Yang, S. U. Choi and K. H. Park, Heterocycles, 2000, 53, 887; (e) M. Godskesen, I. Lundt, R. Madsen and B. Winchester, Bioorg. Med. Chem., 1996, 4, 1857; (f) G. Legier, A. E. Stütz and H. Immich, Carbohydr. Res., 1995, 272, 17; (g) D. Sames and R.Polt, Synlett, 1995, 552; (h) T. Tschamber, F. Backenstrass, M. Neuberger, M. Zhender and J. Streith, Tetrahedron, 1994, 50, 1135.
37. For 3,4,5-piperidine triol syntheses, see refs 5(a), 7 and (a) H. Han, Tetrahedron Lett., 2003, 44, 1567; (b) N. T. Patil, S. John, S. G. Sabharwal and D. D. Dhawale, Bioorg. Med. Chem., 2002, 10, 2155; (c) M. Amat, N. Llor, M. Huguet, E. Molins, E. Espinosa and J. Bosch, Org. Lett., 2001, 3, 3257; (d) K. C. Jang, I.-Y. Jeong, M. S. Yang, S. U. Choi and K. H. Park, Heterocycles, 2000, 53, 887; (e) M. Godskesen, I. Lundt, R. Madsen and B. Winchester, Bioorg. Med. Chem., 1996, 4, 1857; (f) G. Legier, A. E. Stütz and H. Immich, Carbohydr. Res., 1995, 272, 17; (g) D. Sames and R.Polt, Synlett, 1995, 552; (h) T. Tschamber, F. Backenstrass, M. Neuberger, M. Zhender and J. Streith, Tetrahedron, 1994, 50, 1135.
38. For 3,4,5-piperidine triol syntheses, see refs 5(a), 7 and (a) H. Han, Tetrahedron Lett., 2003, 44, 1567; (b) N. T. Patil, S. John, S. G. Sabharwal and D. D. Dhawale, Bioorg. Med. Chem., 2002, 10, 2155; (c) M. Amat, N. Llor, M. Huguet, E. Molins, E. Espinosa and J. Bosch, Org. Lett., 2001, 3, 3257; (d) K. C. Jang, I.-Y. Jeong, M. S. Yang, S. U. Choi and K. H. Park, Heterocycles, 2000, 53, 887; (e) M. Godskesen, I. Lundt, R. Madsen and B. Winchester, Bioorg. Med. Chem., 1996, 4, 1857; (f) G. Legier, A. E. Stütz and H. Immich, Carbohydr. Res., 1995, 272, 17; (g) D. Sames and R.Polt, Synlett, 1995, 552; (h) T. Tschamber, F. Backenstrass, M. Neuberger, M. Zhender and J. Streith, Tetrahedron, 1994, 50, 1135.
39. For 3,4,5-piperidine triol syntheses, see refs 5(a), 7 and (a) H. Han, Tetrahedron Lett., 2003, 44, 1567; (b) N. T. Patil, S. John, S. G. Sabharwal and D. D. Dhawale, Bioorg. Med. Chem., 2002, 10, 2155; (c) M. Amat, N. Llor, M. Huguet, E. Molins, E. Espinosa and J. Bosch, Org. Lett., 2001, 3, 3257; (d) K. C. Jang, I.-Y. Jeong, M. S. Yang, S. U. Choi and K. H. Park, Heterocycles, 2000, 53, 887; (e) M. Godskesen, I. Lundt, R. Madsen and B. Winchester, Bioorg. Med. Chem., 1996, 4, 1857; (f) G. Legier, A. E. Stütz and H. Immich, Carbohydr. Res., 1995, 272, 17; (g) D. Sames and R.Polt, Synlett, 1995, 552; (h) T. Tschamber, F. Backenstrass, M. Neuberger, M. Zhender and J. Streith, Tetrahedron, 1994, 50, 1135.
40. For 3,4,5-piperidine triol syntheses, see refs 5(a), 7 and (a) H. Han, Tetrahedron Lett., 2003, 44, 1567; (b) N. T. Patil, S. John, S. G. Sabharwal and D. D. Dhawale, Bioorg. Med. Chem., 2002, 10, 2155; (c) M. Amat, N. Llor, M. Huguet, E. Molins, E. Espinosa and J. Bosch, Org. Lett., 2001, 3, 3257; (d) K. C. Jang, I.-Y. Jeong, M. S. Yang, S. U. Choi and K. H. Park, Heterocycles, 2000, 53, 887; (e) M. Godskesen, I. Lundt, R. Madsen and B. Winchester, Bioorg. Med. Chem., 1996, 4, 1857; (f) G. Legier, A. E. Stütz and H. Immich, Carbohydr. Res., 1995, 272, 17; (g) D. Sames and R.Polt, Synlett, 1995, 552; (h) T. Tschamber, F. Backenstrass, M. Neuberger, M. Zhender and J. Streith, Tetrahedron, 1994, 50, 1135.
41. For 3,4,5-piperidine triol syntheses, see refs 5(a), 7 and (a) H. Han, Tetrahedron Lett., 2003, 44, 1567; (b) N. T. Patil, S. John, S. G. Sabharwal and D. D. Dhawale, Bioorg. Med. Chem., 2002, 10, 2155; (c) M. Amat, N. Llor, M. Huguet, E. Molins, E. Espinosa and J. Bosch, Org. Lett., 2001, 3, 3257; (d) K. C. Jang, I.-Y. Jeong, M. S. Yang, S. U. Choi and K. H. Park, Heterocycles, 2000, 53, 887; (e) M. Godskesen, I. Lundt, R. Madsen and B. Winchester, Bioorg. Med. Chem., 1996, 4, 1857; (f) G. Legier, A. E. Stütz and H. Immich, Carbohydr. Res., 1995, 272, 17; (g) D. Sames and R.Polt, Synlett, 1995, 552; (h) T. Tschamber, F. Backenstrass, M. Neuberger, M. Zhender and J. Streith, Tetrahedron, 1994, 50, 1135.
42. (a) G. Pandey and M. Kapur, Tetrahedron Lett., 2000, 41, 8821;
43. (b) G. Pandey and M. Kapur, Synthesis, 2001, 1263.
44. (a) G. Pandey, G. Kumaraswamy and U. T. Bhalerao, Tetrahedron Lett., 1989, 30, 6059;
45. G. Pandey, G. D. Reddy and G. Kumaraswamy, Tetrahedron, 1994, 50, 8185.
46. G. Pandey and M. Kapur, Org. Lett., 2002, 4, 3883.
47. (a) O. Mitsunobu and M. Yamada, Bull. Chem. Soc. Jpn., 1967, 40, 2380;
48. (b) O. Mitsunobu, Synthesis, 1981, 1;
49. (c) D. L. Huges, R. A. Reamer, J. J. Bergan and E. J. J. Grabowski, J. Am. Chem. Soc., 1988, 110, 6487.
50. H. lida, N. Yamazaki and C. Kibayashi, J. Org. Chem., 1987, 52, 3337.
51. S. K. Kang and S. B. Lee, Chem. Commun., 1998, 761.