First stereocontrolled synthesis and biological evaluation of 1,6-dideoxy-L-nojirimycin

Tetrahedron Asymmetry

Volumn 14, Issue 1, 2003, Pages 47-51

  Bordier, Aymeric ^a   Compain, Philippe ^a   Martin, Olivier R ^a   Ikeda, Kyoko ^b   Asano, Naoki ^b  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b HOKURIKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 IMINOALDITOL; 1,6 DIDEOXY LEVO NOJIRIMYCIN; ALDITOL; GLYCOSIDASE INHIBITOR; NOJIRIMYCIN; UNCLASSIFIED DRUG; XYLOSE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 0037421266     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00752-8     Document Type: Article

References (38)

1. Stütz A.E. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond. 1999;Wiley-VCH, Weinheim.
2. Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 11:2000;1645.
3. For a review on carbohydrate mimetic-based glycosyltransferase inhibitors, see: Compain P., Martin O.R. Bioorg. Med. Chem. 9:2001;3077.
4. Fedorov A., Shi W., Kicska G., Fedorov E., Tyler P.C., Furneaux R.H., Hanson J.C., Gainsford G.J., Larese J.Z., Schramm V.L., Almo S.C. Biochemistry. 40:2001;853.
5. Miles R.W., Tyler P.C., Furneaux R.H., Bagdassarian C., Schramm V.L. Biochemistry. 37:1998;8615.
6. Kline P.C., Schramm V.L. Biochemistry. 32:1993;13212.
7. Jakobsen P., Lundbeck J.M., Kristiansen M., Breinholt J., Demuth H., Pawlas J., Torres Candela M.P., Andersen B., Westergaard N., Lundgren K., Asano N. Bioorg. Med. Chem. 9:2001;733.
8. Lee R.E., Smith M.D., Pickering L., Fleet G.W.J. Tetrahedron Lett. 40:1999;8689.
9. 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., Fleet G.W.J. Tetrahedron Lett. 38:1997;6733.
10. Iminosugars: Recent Insights Into Their Bioactivity and Potential As Therapeutic Agents. Curr. Top. Med. Chem.; Martin, O. R.; Compain, P., Eds.; Bentham: Hilversum, Netherlands, in press.
11. Häusler H., Kawakami P., Mlaker E., Severn W.B., Wrodnigg T.M., Stütz A.E. J. Carbohydr. Chem. 19:2000;435.
12. Durantel D., Branza-Nichita N., Carrouee-Durantel S., Butters T.D., Dwek R.A., Zitzmann N. J. Virol. 75:2001;8987.
13. Goss P.E., Baker M.A., Carver J.P., Dennis J.W. Clin. Cancer Res. 1:1995;935.
14. Humphries M.J., Matsumoto K., White S.L., Olden K. Cancer Res. 46:1986;5215.
15. Nishimura Y., Satoh T., Adachi H., Kondo S., Takeuchi T., Azetaka M., Fukuyasu H., Izuka Y. J. Med. Chem. 40:1997;2626.
16. Butters T.D., Dwek A., Platt F.M. Chem. Rev. 100:2000;4683.
17. Alper J. Science. 291:2001;2338.
18. Cox T., Lachmann R., Hollak C., Aerts J., van Weely S., Hrebicek M., Platt F., Butters T., Dwek R., Moyses C., Gow I., Elstein D., Zimran A. The Lancet. 355:2000;1481.
19. Kajimoto T., Liu K.K.-C., Pederson R.L., Zhong Z., Ichikawa Y., Porco J.A., Wong C.-H. J. Am. Chem. Soc. 113:1991;6187.
20. Di J., Rajanikanth B., Szarek W.A. J. Chem. Soc., Perkin Trans. 1. 1992;2151.
21. Defoin A., Sarazin H., Streith J. Helv. Chim. Acta. 79:1996;560.
22. Dhavale D.D., Saha N.N., Desai V.N. J. Org. Chem. 62:1997;7482.
23. Pistia G., Hollingsworth R.I. Carbohydr. Res. 328:2000;467.
24. Renaud P., Millet J., Sepulchre C., Theveniaux J., Barberousse V., Jeanneret V., Vogel P. Helv. Chim. Acta. 81:1998;2043.
25. Streicher H., Meisch J., Bohner C. Tetrahedron. 57:2001;8851.
26. Godin G., Compain P., Masson G., Martin O.R. J. Org. Chem. 67:2002;6960.
27. Masson G., Compain P., Martin O.R. Org. Lett. 2:2000;2971.
28. Bloch R. Chem. Rev. 98:1998;1407.
29. Dhavale D.D., Desai V.N., Sindkhedkar M.D., Mali R.S., Castellari C., Trombini C. Tetrahedron: Asymmetry. 8:1997;1475.
30. For a pioneering study on the addition of organomagnesium reagents to 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose, see: Wolfrom M.L., Hanessian S. J. Org. Chem. 27:1962;1800.
31. One example of a diastereoselective chain extension of 3-O-methyl-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose N-p-anisylimine using 2-(trimethylsiloxy)furan has been reported in the literature: Casiraghi G., Colombo L., Rassu G., Spanu P. J. Org. Chem. 55:1990;2565.
32. 3 requires 148.0974).
33. Yasuda K., Kizu H., Yamashita T., Kameda Y., Kato A., Nash R.J., Fleet G.W.J., Molyneux R.J., Asano N. J. Nat. Prod. 65:2002;198.
34. Winchester B., Barker S., Baines S., Jacob G.S., Namgoong S.K., Fleet G.W.J. Biochem. J. 265:1990;277.
35. Davis B.G., Hull A., Smith C., Nash R.J., Watson A.A., Winkler D.A., Griffiths R.C., Fleet G.W.J. Tetrahedron: Asymmetry. 9:1998;2947. and references cited therein.
36. Wong C.-H., Provencher L., Porco J.A., Jung S.-H., Wang Y.-F., Chen L., Wang R., Steensma D.H. J. Org. Chem. 60:1995;1492.
37. Paulsen H., Matzke M., Nuck R., Orthen B., Reutter W. Liebigs Ann. Chem. 1990;953.
38. Legler S., Stütz A.E., Immich H. Carbohydr. Res. 272:1995;17.