Synthesis and l-fucosidase inhibitory activity of a new series of cyclic sugar imines-in situ formation and assay of their saturated counterparts

Tetrahedron Letters

Volumn 50, Issue 31, 2009, Pages 4498-4501

  Behr, Jean Bernard ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Glycosidases; Imines; Nitriles; Nucleophilic additions; Tandem reactions

Indexed keywords

ALPHA LEVO FUCOSIDASE; GLYCOSIDASE INHIBITOR; IMINE; IMINOSUGAR; NUCLEOPHILE; PYRROLIDINE DERIVATIVE; SODIUM BOROHYDRIDE;

ADDITION REACTION; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME INHIBITION; IC 50; INHIBITION KINETICS; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 67049159824     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.075     Document Type: Article

References (42)

1. Iminosugars: Recent Insights into their Bioactivity and Potential as Therapeutic Agents: Martin, O. R., Compain, P., Eds. Curr. Top. Med. Chem. 2003, 3, 5.
2. Compain P., and Martin O.R. Iminosugars: From Synthesis to Therapeutic Applications (2007), Wiley-VCH, Weinheim
3. Sinnott M.L. Chem. Rev. 90 (1990) 117-202
4. Moreno-Vargas A.J., Robina I., Demange R., and Vogel P. Helv. Chim. Acta 86 (2003) 1894-1913
5. Wu C.-Y., Chang C.-F., Chen J., Wong C.-H., and Lin C.-H. Angew. Chem., Int. Ed. 42 (2003) 4661-4664
6. Kato A., Kato N., Kano E., Adachi I., Ikeda K., Yu L., Okamoto T., Banba Y., Ouchi H., Takahata H., and Asano N. J. Med. Chem. 48 (2005) 2036-2044
7. Laroche C., Behr J.-B., Szymoniak J., Bertus P., Schütz C., Vogel P., and Plantier-Royon R. Bioorg. Med. Chem. 14 (2006) 4047-4054
8. Dubernet M., Defoin A., and Tarnus C. Bioorg. Med. Chem. Lett. 16 (2006) 1172-1174
9. Li H., Liu T., Zhang Y., Favre S., Bello C., Vogel P., Butters T., Oikonomakos N.G., Marrot J., and Bleriot Y. ChemBioChem 9 (2008) 253-260
10. Mitchell M.C., Tian F., Lee L.V., and Wong C.-H. Angew. Chem., Int. Ed. 41 (2002) 3041-3044
11. Bryan M.C., Lee L.V., and Wong C.-H. Bioorg. Med. Chem. Lett. 14 (2004) 3185-3188
12. Lin T.-W., Chang W.-W., Chen C.-C., and Tsai Y.-C. Biochem. Biophys. Res. Commun. 331 (2005) 953-957
13. Chevrier C., Le Nouen D., Defoin A., and Tarnus C. Eur. J. Org. Chem. (2006) 2384-2392
14. Shimanek E., McGarvey E.J., Jablonowski J.A., and Wong C.-H. Chem. Rev. 98 (1998) 833-862
15. Robina I., Moreno-Vargas A.J., Carmona A.T., and Vogel P. Curr. Drug Metabol. 5 (2004) 329-361
16. Khunnsook S., Bean B., McGowan S.R., and Alhadeff J.A. Biol. Reprod. 68 (2003) 709-716
17. Takayama S., Martin R., Wu J., Laslo K., Siuzdak G., and Wong C.-H. J. Am. Chem. Soc. 119 (1997) 8146-8151
18. Behr J.-B., Gainvors-Claisse A., and Belarbi A. Nat. Prod. Res. 20 (2006) 1308-1314
19. Cipolla L., Fernandes M.R., Gregori M., Airoldi C., and Nicotra F. Carbohydr. Res. 342 (2007) 1813-1830
20. Pearson M., Plantier-Royon R., Szymoniak J., Bertus P., and Behr J.-B. Synthesis (2007) 3589-3594
21. Racine E., Bello C., Gerber-Lemaire S., Vogel P., and Py S. J. Org. Chem. 74 (2009) 1766-1769
22. Behr J.-B., Pearson M., Bello C., Vogel P., and Plantier-Royon R. Tetrahedron: Asymmetry 19 (2008) 1829-1832
23. Moreno-Clavijo E., Carmona A.T., Vera-Ayoso Y., Moreno-Vargas A.J., Bello C., Vogel P., and Robina I. Org. Biomol. Chem. 7 (2009) 1192-1202
24. For a general synthetic method, see. Moriarty R.M., Mitan C.A., Branza-Nichita N., Phares K.R., and Parrish D. Org. Lett. 8 (2006) 3465-3469
25. For other examples of cyclic sugar imines, see:. Bouix C., Bisseret P., and Eustache J. Tetrahedron Lett. 39 (1998) 825-828
26. Schuster M., and Blechert S. Tetrahedron: Asymmetry 10 (1999) 3139-3145
27. Davis B.G., Maughan M.A., Chapman T.M., Villard R., and Courtney S. Org. Lett. 4 (2002) 103-106
28. Izquierdo I., Plaza M.T., Rodríguez M., Franco F., and Martos A. Tetrahedron 61 (2005) 11697-11704
29. Hotchkiss D.J., Kato A., Odell B., Claridge T.D.W., and Fleet G.W.J. Tetrahedron: Asymmetry 18 (2007) 500-512
30. Behr J.-B., Kalla A., Harakat D., and Plantier-Royon R. J. Org. Chem. 73 (2008) 3612-3615
31. Defoin A., Joubert M., Henchel J.-M., Strehler C., and Streith J. Synthesis (2000) 1719-1726
32. March J. Advanced Organic Chemistry. 4th ed. (1992), Wiley and Sons, New York pp 441-442
33. Weidmann H., Wolf N., and Timpe W. Carbohyd. Res. 24 (1972) 184-187
34. Hutchins R.O., Kandasamy D., Maryanoff C., Masilamani D., and Maryanoff B.E. J. Org. Chem. 42 (1977) 82-91
35. Lonn H., and Lonngren J. Carbohydr. Res. 132 (1984) 39-44
36. Rifé J., and Ortuno R.M. Tetrahedron: Asymmetry 10 (1999) 4245-4260
37. Furukawa J.-I., Kobayashi S., Nomizu M., Nishi N., and Sakairi N. Tetrahedron Lett. 41 (2000) 3453-3457
38. Thomas S., Huynh T., Enriquez-Rios V., and Singaram B. Org. Lett. 3 (2001) 3915-3918
39. Theodore L.J., and Nelson W.L. J. Org. Chem. 52 (1987) 1309-1315
40. 3)
41. See Supplementary data.
42. 4 reduction of such ketimines is usually not selective (see Ref. 9); thus, we assume that the two possible stereoisomers are formed during the reaction. Indeed, preliminary NMR analysis of a sample of 4b revealed the presence of the two possible isomers (two doublets at 1.3 ppm, 2 × 5-Me).