Synthesis of 5a-carba-hexopyranoses and hexopyranosylamines, as well as 5a,5a′-dicarbadisaccharides, from 3,8-dioxatricyclo[4.2.1.0 2,4]nonan-9-ol: Glycosidase inhibitory activity of N-substituted 5a-carba-β-gluco- and β-galactopyranosylamines, and derivatives thereof

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 20, 2004, Pages 5183-5188

  Ogawa, Seiichiro ^a   Funayama, Sho ^a   Okazaki, Kensuke ^a   Ishizuka, Fumito ^a   Sakata, Yoko ^a   Doi, Fuminao ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA GALACTOSIDASE; AMINE; DISACCHARIDE; GLUCOSE DERIVATIVE; GLYCOSIDASE; GLYCOSIDASE INHIBITOR; GLYCOSYLTRANSFERASE INHIBITOR; PYRAN DERIVATIVE;

ARTICLE; COFFEE; IC 50; SYNTHESIS;

ALKANES; AMINO SUGARS; DISACCHARIDES; GALACTOSE; GLYCOSIDE HYDROLASES; HETEROCYCLIC COMPOUNDS, 3-RING;

EID: 4544369197     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.07.091     Document Type: Article

References (26)

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2. J. Matsuda, O. Suzuki, A. Oshima, Y. Yamamoto, A. Noguchi, K. Takimoto, M. Itoh, Y. Matsuzaki, Y. Yasuda, S. Ogawa, Y. Sakata, E. Nanba, K. Higaki, Y. Ogawa, L. Tominaga, K. Ohno, H. Iwasaki, H. Watanabe, R.O. Brandy, and Y. Suzuki Proc. Natl. Acad. Sci. U.S.A. 100 2003 15912
3. K. Okazaki, S. Nishigaki, F. Ishizuka, Y. Kajihara, and S. Ogawa Org. Biomol. Chem. 1 2003 2229
4. S. Ogawa, M. Oya, T. Toyokuni, N. Chida, and T. Suami Bull. Chem. Soc. Jpn. 56 1983 1441
5. S. Ogawa, M. Mori, G. Takeuchi, F. Doi, M. Watanabe, and Y. Sakata Bioorg. Med. Chem. Lett. 12 2002 2811
6. S. Ogawa, K. Nakamoto, M. Takahara, Y. Tanno, N. Chida, and T. Suami Bull. Chem. Soc. Jpn. 52 1979 1174
7. gem = 16.1 Hz, H-5a(endo)]
8. gem = 14.4 Hz, H-5a(endo)]
9. The reaction conditions have not been optimized yet
10. 5,6exo = 7.8 Hz, H-5), 2.34-.37 (m, 2H, H-5a,5a)
11. S. Ogawa, H. Aoyama, and T. Sato Carbohydr. Res. 337 2002 1979 1992
12. Aoyama, H.; Ogawa, S.; Sato, T. In preparation
13. Y. Miura, T. Arai, and T. Yamagata Carbohydr. Res. 289 1996 193
14. Y. Miura, and T. Yamagata Biochem. Biophys. Res. Commun. 241 1997 698
15. H. Nakajim, Y. Miura, and T. Yamagata J. Biochem. 124 1998 148
16. M. Carmelita, Z. Kasuya, L.X. Wang, Y.C. Lee, M. Mitsuki, H. Nakajima, Y. Miura, T. Sato, K. Hatanaka, S. Yamagata, and T. Yamagata Cabohydr. Res. 329 2000 755 763
17. Exhaustive acetolysis of 3i is likely to give 6g selectively; however, prolonged heating of intermediate 6f and/or 6g under these conditions might cause substitution as well as elimination to give rise to aromatic compounds. Therefore, careful optimization should be worked out for the acetolysis
18. 3)
19. gem = 13.2 Hz, H-5a(ax)]
20. gem = 12.5 Hz, H-5a′ax)
21. 4 (40:20:1), 80-95°C], de-O-methylation was partly accompanied with opening of the anhydro ring and the benzyl ether group remained almost unaffected, contrary to the cases of 3d and 3f. Therefore, initial removal of the benzyl ether group by hydrogenolysis, followed by acetolysis, would be an effective route to furnish free N-linked dicarbadisaccharides. Furthermore, in order to get the 1-O-alkyl derivatives in acceptable yields, the acetolysis conditions should be optimized in each cases
22. All compounds were assayed for activity against six glycosidases: α-galactosidase (green coffee beans), β-galactosidase (bovine liver), α-glucosidase (Baker's yeast), β-glucosidase (almond), α-fucosidase (bovine kidney), α-mannosidase (Jack beans). Biological assays were carried out in a standard manner by Drs. A. Takahashi and A. Tomoda (Hokko Chemical Industries, Co. Ltd, Toda, Atsugi, Japan)
23. Some N-alkyl derivatives of 6h were synthesized for the purpose of comparing their activity with those of 6-deoxy congeners, the antipodes of α-fucopyranosylamine-type inhibitors. They have been shown to possess strong inhibitory activity against β-galactosidase and β-glucosidase, as well as α-galactosidase: Ogawa, S.; Fujieda, M.; Sakata, Y., in preparation
24. With a series of N-alkyl-5a-carba-β-galactopyranosylamines, deoxylation at C-6 resulted in drastic change in potential and specificity of inhibitory activity: S. Ogawa, S. Fujieda, Y. Sakata, M. Ishizaki, S. Hisamatsu, and K. Okazaki Bioorg. Med. Chem. Lett. 13 2003 3461 3463
25. S. Ogawa, M. Ashiura, C. Uchida, S. Watanabe, C. Yamazaki, K. Yamagishi, and J. Inokuchi Bioorg. Med. Chem. Lett. 6 1996 929
26. S. Ogawa, Y. Kobayashi, K. Kabayama, M. Jimbo, and J. Inokuchi Bioorg. Med. Chem. 6 1998 1955