Polyhydroxyazepanes mimicking monosaccharides: Synthesis of an α-D-galacto-like iminoheptitol

Heterocycles

Volumn 64, Issue , 2004, Pages 65-74

  Li, Hongqing ^a   Blériot, Yves ^a   Mallet, Jean Maurice ^a   Zhang, Yongmin ^a   Rodriguez Garcia, Eliazar ^b   Vogel, Pierre ^b   Mari, Silvia ^c   Jiménez Barbero, Jesús ^c   Sinaÿ, Pierre ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

^b SWISS FEDERAL INSTITUTE OF TECHNOLOGY   (Switzerland)

^c CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 13144262401     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-04-S(P)45     Document Type: Article

References (40)

1. Lillelund V.H., Jensen H.H., Liang X., and Bols M. Chem. Rev. 102 (2002) 515
2. Martin O.R., and Compain P. Curr. Top. Med. Chem. 3 (2003) i-iv
3. Mitrakou A., Tountas N., Raptis A.E., Bauer R.J., Schulz H., and Raptis S.A. Diab. Med. 15 (1998) 657
4. Butters T.D., Dwek R.A., and Platt F.M. Curr. Top. Med. Chem. 3 (2003) 561
5. Groopman J.E. Rev. Infect. Dis. 12 (1990) 908
6. Robina I., Moreno-Vargas A.J., Carmona A.T., and Vogel P. Current Drug Metabolism 5 (2004) 329
7. Jan. Laver W.G., Bischofberger N., and Webster R.G. Sci. Am. (1999) 78
8. Greimel P., Spreitz J., Stütz A.E., and Wrodnigg T.M. Curr. Top. Med. Chem. 3 (2003) 513
9. Zitzmann N., Mehta A.S., Carrouée S., Butters T.D., Platt F.M., McCauley J., Blumberg B.S., Dwek R.A., and Block T.M. PNAS 96 (1999) 11878
10. Heightman T.D., and Vasella A.T. Angew. Chem. Int. Ed. 38 (1999) 750
11. Vasella A., Davies G.J., and Böhm M. Curr. Op. Chem. Biol. 6 (2002) 619
12. Stütz A. Iminosugars as glycosidase inhibitors: Nojirimycin and Beyond (1999), Wiley-VCH, N.Y.
13. For tetrahydroxyazepanes see. Paulsen H., and Todt K. Chem. Ber. 100 (1967) 512
14. Dax R., Gaigg B., Grassberger B., Koelblinger B., and Stütz A.E. J. Carb. Chem. 9 (1990) 479
15. Lohray B.B., Jayamma Y., and Chatterjee M. J. Org. Chem. 60 (1995) 5958
16. Qian X.-H., Moris-Varas F., and Wong C.-H. Bioorg. Med. Chem. Lett. 6 (1996) 1117
17. Moris-Varas F., Qian X.-H., and Wong C.-H. J. Am. Chem. Soc. 118 (1996) 7647
18. Qian X.-H., Moris-Varas F., Fitzgerald M.C., and Wong C.-H. Bioorg. Med. Chem. 4 (1996) 2055
19. Le Merrer Y., Poitout L., Depezay J.-C., Dosbaa I., Geoffroy S., and Foglietti M.-J. Biorg. Med. Chem. 5 (1997) 519
20. Lohray B.B., Bhushan V., Prasuna G., Jayamma Y., Raheem M.A., Papireddy P., Umadevi B., Premkumar M., Lakshmi N.S., and Narayanareddy K. Indian J. Chem., Sect. B 38B (1999) 1311
21. Painter G.F., and Falshaw A. J. Chem. Soc., Perkin Trans I (2000) 1157
22. Johnson H.A., and Thomas N.R. Bioorg. Med. Chem. Chem. Lett. 12 (2002) 237
23. Andreana P.R., Sanders T., Janezuk A., Warrick J.I., and Wang P.G. Tetrahedron Lett. 43 (2002) 6525
24. Joseph C.C., Regeling H., Zwanenburg B., and Chittenden G.J.F. Tetrahedron 58 (2002) 6907
25. Fuentes J., Gasch C., Olano D., Pradera M.A., Repetto G., and Sayago F.J. Tetrahedron: Asymmetry 13 (2002) 1743
26. Painter G.F., Eldridge P.G., and Falshaw A. Bioorg. Med. Chem. 12 (2004) 225
27. Godin G., Garnier E., Compain P., Martin O.R., Ikeda K., and Asano N. Tetrahedron Lett. 45 (2004) 579
28. Li H., Blériot Y., Chantereau C., Mallet J.-M., Sollogoub M., Zhang Y., Rodriguez-Garcia E., Vogel P., Jimenez-Barbero J., and Sinaÿ P. Org. Biomol. Chem. 2 (2004) 1492
29. Dhivale D.D., Markad S.D., Karanjule N.S., and PrakashaReddy J. J. Org. Chem. 69 (2004) 4760
30. For recent reviews on olefin metathesis, see. Fürstner A. Angew. Chem. 112 (2000) 3140
31. Fürstner A. Angew. Chem., Int. Ed. 39 (2000) 3012
32. Trnka T.M., and Grubbs R.H. Acc. Chem. Res. 34 (2001) 18
33. Grubbs R.H. Tetrahedron 60 (2004) 7117
34. Fleet G.W.J., Petursson S., Campbell A.L., Müller R.A., Behling J.R., Babiak K.A., Ng J.S., and Scarosc M.G. J. Chem. Soc. Perkin Trans I (1989) 665
35. Godskesen M., Lundt I., and Sotofte I. Tetrahedron: Asymmetry 11 (2000) 567
36. w=0.0502; Crystallographic data (excluding structure factors) have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 250899. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.ukl.
37. +): 194.1028, Found 194.1021.
38. A known protocol was applied:. Saul R., Chambers J.P., Molyneux R.J., and Elbein A.D. Arch. Biochem. Biophys. 221 (1983) 593. We verified that the delay of inhibitor/enzyme incubation did not affect the inhibition measurements. Under standard conditions, optimal inhibitory activities were measured after five minutes of incubation.
39. Brandi A., Cicchi S., Cordero F.M., Frignoli B., Goti A., Picasso S., and Vogel P. J. Org. Chem. 60 (1995) 6806. We verified that the delay of inhibitor/enzyme incubation did not affect the inhibition measurements. Under standard conditions, optimal inhibitory activities were measured after five minutes of incubation.
40. Martinez-Mayorga K., Medina-Franco J.L., Mari S., Canada F.J., Rodriguez-Garcia E., Vogel P., Li H., Blériot Y., Sinaÿ P., and Jiménez-Barbero J. Eur. J. Org. Chem. 20 (2004) 4119