A facile synthesis of D-glucose-type gem-diamine 1-N-iminosugars: A new family of glucosidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 6, 1999, Pages 1241-1246

  Shitara, Eiki ^a   Nishimura, Yoshio ^a   Kojima, Fukiko ^a   Takeuchi, Tomio ^a  

^a INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE DERIVATIVE; ENZYME INHIBITOR; GLUCOSIDASE;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; METASTASIS INHIBITION; NONHUMAN;

ASPERGILLUS NIGER; ENZYME INHIBITORS; GLUCOSIDASES; PIPERIDINES; STREPTOMYCES;

STREPTOMYCES;

EID: 0032973908     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00048-6     Document Type: Article

References (36)

1. Karlsson, G. B.; Butters, T. D.; Dwek, R. A.; Platt, F. M. J. Biol. Chem. 1993, 268, 570.
2. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199.
3. Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182.
4. Nishimura Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol. 10, pp 495-583.
5. Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1995; Vol. 16, pp 75-121.
6. (a) Cordes, E. H.; Bull, H. G. Chem. Rev. 1974, 74, 581.
7. (b) Perkins, S. J.; Johnson, L. N.; Philips, D. C.; Dwek, R. A. Biochem. J. 1981, 193, 553.
8. (c) Sinnott, M. L. Chem. Rev. 1990, 90, 1171.
9. (d) Kajimoto, T.; Liu, K. K.-C.; Pederson, R. L.; Zhong, Z.; Ichikawa, Y.; Porco, Jr. J. A.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6187.
10. (e) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007.
11. Nishimura, Y.; Satoh, T.; Kondo, S.; Takeuchi, T.; Azetaka, M.; Fukuyasu, H.; Iizuka, Y.; Shibahara, S. J. Antibiotics 1994, 47, 840.
12. Satoh, T.; Nishimura, Y.; Kondo, S.; Takeuchi, T.; Azetaka, M.; Fukuyasu, H.; Iizuka, Y.; Oouchi, S.; Shibahara, S. J. Antibiotics 1996, 49, 321.
13. Nishimura, Y.; Satoh, T.; Kudo, T.; Kondo, S.; Takeuchi, T. Bioorg. Med. Chem. 1996, 4, 91.
14. Nishimura, Y.; Satoh, T.; Adachi, H.; Kondo, S.; Takeuchi, T.; Azetaka, M.; Fukuyasu, H.; Iizuka, Y. J. Am. Chem. Soc. 1996, 118, 3051; J. Med. Chem. 1997, 40, 2626.
15. (a) Humphries, M. J.; Matsumono, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215.
16. (b) Atsumi, S.; Nosaka, C.; Ochi, Y.; Iinuma, H.; Umezawa, K. Cancer Res. 1993, 53, 4896.
17. (a) Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Natl. Acad. Sci. USA 1988, 85, 9229.
18. (b) Taylor, D. L.; Sunkara, P. S.; Liu, P. S.; Kang, M. S.; Bowlin, T. L.; Tyms, A. S. AIDS 1991, 5, 693.
19. (c) Shimizu, H.; Tsuchie, H.; Yoshida, K.; Morikawa, S.; Tsuruoka, T.; Yamamoto, H.; Ushijima, H.; Kitamura, T. AIDS 1990, 4, 975.
20. (a) Joubert, P. H.; Venter, C. P.; Joubert, H. F.; Hillebrand, I. Eur. J. Pharmacol. 1985, 28, 705.
21. (b) Anzeveno, P. B.; Creemer, L. J.; Daniel, J. K.; King, C.-H.; Liu, P. S. J. Org. Chem. 1989, 54, 2539.
22. (c) Balfour, J. A.; McTavish, D. Drugs 1993, 46, 1025.
23. (d) Truscheit, E.; Frommer, W.; Junge, B.; Mueller, L.; Schmidt, D. D.; Wingender, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 744.
24. Umezawa, H.; Aoyagi, T.; Komiyama, T., Morishima, H.; Hamada, M.; Takeuchi, T. J. Antibiotics 1974, 27, 963.
25. Nishimura, Y.; Satoh, T.; Kudo, T.; Kondo, S.; Takeuchi, T. Bioorg. Med. Chem. 1996, 4, 91.
26. Shitara, E.; Nishimura, Y.; Kojima, F.; Takeuchi, T. J. Antibiotics, in press.
27. Mitsunobu, O. Synthesis 1981, 1.
28. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277; J. Org. Chem. 1983, 48, 4156.
29. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277; J. Org. Chem. 1983, 48, 4156.
30. Halvorson, H. O.; Ellias, L. Biochim. Biophys. Acta 1958 30 28.
31. Kobayashi, A. Agr. Biol. Chem. 1962, 26, 203.
32. Liu, Y.-T. J. Biol. Chem. 1967, 242, 5474.
33. Craven, G. R.; Steers, Jr. E.; Anfinsen, C. B. J. Biol. Chem. 1965, 240, 2468.
34. Stahl, P. P. D.; Fishman, W. H. In Methods of Enzymatic Analysis; Voigt, K. D., Ed.; Academic Press: New York, 1974; Vol. 4, pp 246-256.
35. Uda, Y.; Li, S.-C.; Li, Y.-T. J. Biol. Chem. 1977, 252, 5194.
36. Aoyagi, T.; Suda, H.; Uotani, K.; Kojima, F.; Aoyama, T.; Horiguchi, K.; Hamada, M.; Takeuchi, T. J. Antibiotics 1992, 45, 1404.