The spirocyclopropyl moiety as a methyl surrogate in the structure of l-fucosidase and l-rhamnosidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 23, 2009, Pages 8020-8026

  Pearson, Morwenna S M ^a   Floquet, Nicolas ^b   Bello, Claudia ^c   Vogel, Pierre ^c   Plantier Royon, Richard ^a   Szymoniak, Jan ^a   Bertus, Philippe ^d   Behr, Jean Bernard ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b UNIVERSITÉ DE MONTPELLIER   (France)

^c EPFL   (Switzerland)

^d UNIVERSITÉ DU MAINE   (France)

Author keywords

Glycosidases; Iminosugars; Inhibition; Spiro compounds

Indexed keywords

ALPHA LEVO FUCOSIDASE; ALPHA LEVO FUCOSIDASE INHIBITOR; ENZYME; ENZYME INHIBITOR; RHAMNOSIDASE; RHAMNOSIDASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLOPROPANATION; DRUG ACTIVITY; DRUG STRUCTURE; ENZYME INHIBITION;

ALPHA-L-FUCOSIDASE; CYCLOPROPANES; ENZYME INHIBITORS; FUCOSE; GLYCOSIDE HYDROLASES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; RHAMNOSE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPIRO COMPOUNDS;

EID: 72149091755     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.10.010     Document Type: Article

References (57)

1. Flowers H.M. Adv. Carbohydr. Chem. Biochem. 39 (1981) 279
2. Feizi T. Trends Biochem. Sci. 15 (1990) 330
3. Feizi T., and Childs R.A. Biochem. J. 245 (1987) 1
4. Nishihara S., Narimatsu H., Iwasaki H., Yazawa S., Akamatsu S., Ando T., Seno T., and Narimatsu I. J. Biol. Chem. 269 (1994) 29271
5. Lowe J.B. Cell 63 (1990) 861
6. Nelson R.M., Venot A., and Bevilacqua M.P. Ann. Res. Cell Dev. Biol. 11 (1995) 601
7. Etzioni A., Frydman M., Pollack S., Avidor I., Philips M.L., Paulson J.C., and Gershoni-Baruch R. New Eng. J. Med. 327 (1992) 1789
8. Philips M.L., Schwartz B.R., Etzioni A., Bayer R., Ochs H.D., Paulson J.C., and Harlan J.M. J. Clin. Invest. 96 (1995) 2898
9. Ayude D., Fernandez-Rodriguez J., Rodriguez-Berrocal F.J., Martinez-Zorzano V.S., de Carlos A., Gil E., and de la Cadena M.P. Oncology 59 (2000) 310
10. Fernandez-Rodriguez J., Ayude D., de la Cadena M.P., Martinez-Zorzano V.S., de Carlos A., Caride-Castro A., de Castro G., and Rodriguez-Berrocal F.J. Cancer Detect. Prev. 24 (2000) 143
11. Perez S., Rodriguez-Carvajal M.A., and Doco T. Biochimie 85 (2003) 5084
12. Tonetti M., Sturla L., Bisso A., Zanardi D., Benatti U., and deFlora A. Biochimie 80 (1998) 923
13. Yu H., Gong J., Zhang C., and Jin F. Chem. Pharm. Bull. 50 (2002) 175
14. Oda Y., Saito K., Ohara-Takada A., and Mori M. J. Biosci. Bioeng. 94 (2002) 321
15. Avigad G. In: Loewus F.A., and Tanner W. (Eds). Plant Carbohydrates 1, Encyclopedia of Plant Physiology (1982), Springer pp 217-347
16. Deng L., Kasper D.L., Krick T.P., and Wessels M.R. J. Biol. Chem. 275 (2000) 7497
17. In: Compain P., and Martin O.R. (Eds). Iminosugars: From Synthesis to Therapeutic Applications (2007), John Wiley and Sons, Chichester, UK
18. Robina I., Moreno-Vargas A.J., Carmona A.T., and Vogel P. Curr. Drug Metab. 5 (2004) 329
19. Behr J.-B. Curr. Med. Chem. (Anti-infective Agents) 2 (2003) 173
20. In: Stütz A.E. (Ed). Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond. Wiley-VCH (1999), Weinheim, Germany
21. Djebaili M., and Behr J.-B. J. Enzym. Inhib. Med. Chem. 20 (2005) 123
22. Gautier-Lefebvre I., Behr J.-B., Guillerm G., and Muzard M. Eur. J. Med. Chem. (2005) 1255
23. Compain P., and Martin O.R. Bioorg. Med. Chem. 9 (2001) 3077
24. Dubernet M., Defoin A., and Tarnus C. Bioorg. Med. Chem. Lett. 16 (2006) 1172
25. Winchester B., Barker C., Baines S., Jacob G.S., Namgoong S.K., and Fleet G. Biochem. J. 265 (1990) 277
26. Chevrier C., LeNouen D., Neuburger M., Defoin A., and Tarnus C. Tetrahedron Lett. 45 (2004) 5363
27. Robina I., Moreno-Vargas A.J., Fernández-Bolaños J.G., Fuentes J., Demange R., and Vogel P. Bioorg. Med. Chem. Lett. 11 (2001) 2555
28. Moreno-Vargas A.J., Robina I., Demange R., and Vogel P. Helv. Chim. Acta 86 (2003) 1894
29. Moreno-Vargas A.J., Carmona A.T., Mora F., Vogel P., and Robina I. Chem. Commun. (2005) 4949
30. 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
31. Behr J.-B. Tetrahedron Lett. 50 (2009) 4498
32. Davis B.G., Hull A., Smith C., Nash R.J., Watson A.A., Winkler D.A., Griffiths R.C., and Fleet G.W.J. Tetrahedron: Asymmetry 9 (1998) 2947
33. For the synthesis of 9, see:. Pearson M.S.M., Plantier-Royon R., Szymoniak J., Bertus P., and Behr J.-B. Synthesis (2007) 3589
34. for previous attempts towards spirocyclopropyl-pyrrolidines, see:. Laroche C., Plantier-Royon R., Szymoniak J., Bertus P., and Behr J.-B. Synlett (2006) 223
35. Laroche C., Behr J.-B., Szymoniak J., Bertus P., Schütz C., Vogel P., and Plantier-Royon R. Bioorg. Med. Chem. 14 (2006) 4047
36. for general aspects of the cyclopropanation of nitriles, see:. Bertus P., and Szymoniak J. Chem. Commun. (2001) 1792
37. Bertus P., and Szymoniak J. Synlett (2007) 1346
38. for the cyclopropanation of benzoylated glucose, see:. Bertus P., Szymoniak J., Jeanneau E., Docsa T., Gergely P., Praly J.-P., and Vidal S. Bioorg. Med. Chem. Lett. 18 (2008) 4774
39. Köln O., and Redlich H. Synthesis (1996) 826
40. Laroche C., Behr J.-B., Bertus P., Szymoniak J., and Plantier-Royon R. Eur. J. Org. Chem. (2005) 5084
41. Kaskar B., Heise G.L., Michalak R.S., and Vishnuvajjala B.R. Synthesis (1990) 1031
42. Barbat J., Gelas J., and Horton D. Carbohydr. Res. 219 (1991) 115
43. Behr J.-B., and Guillerm G. Tetrahedron Lett. 48 (2007) 2369
44. Taylor C.M., Barker W.D., Weir C.A., and Park J.H. J. Org. Chem. 67 (2002) 4466
45. Provencher L., Steensma D.H., and Wong C.-H. Bioorg. Med. Chem. 2 (1994) 1179
46. Behr J.-B., Defoin A., Mahmood N., and Streith J. Helv. Chim. Acta 78 (1995) 1166
47. Behr J.-B., Chevrier C., Defoin A., Tarnus C., and Streith J. Tetrahedron 59 (2003) 543
48. Merino P., Delso I., Tejero T., Cardona F., Marradi M., Faggi E., Parmeggiani C., and Goti A. Eur. J. Org. Chem. (2008) 2929
49. Behr J.-B., Pearson M.S.M., Bello C., Vogel P., and Plantier-Royon R. Tetrahedron: Asymmetry 19 (2008) 1829
50. Fairbanks A.J., Carpenter N.C., Fleet G.W.J., Ramsden N.G., Cenci di Bello I., Winchester B.G., Al-Daher S.S., and Nagahashi G. Tetrahedron 48 (1992) 3365
51. Chevrier C., Defoin A., and Tarnus C. Bioorg. Med. Chem. 15 (2007) 4125
52. Compound 26, see: Ref. 21a; compound 27, see:. Håkansson A.E., van Ameijde J., Horne G., Nash R.J., Wormald M.R., Kato A., Besra G.S., Gurcha S., and Fleet G.W.J. Tetrahedron Lett. 49 (2008) 179
53. compound 28, see:. Kim J.H., Curtis-Long M.J., Seo W.D., Lee J.H., Lee B.W., Yoon Y.J., Kang K.Y., and Park K.H. Bioorg. Med. Chem. Lett. 15 (2005) 4282
54. compound 29, see:. Chapman T.M., Courtney S., Hay P., and Davis B.G. Chem. Eur. J. 9 (2003) 3397
55. Palmer A.M., and Jäger V. Eur. J. Org. Chem. (2001) 2547
56. Saul R., Chambers J.P., Molyneux R.J., and Elbein A.D. Arch. Biochem. Biophys. 221 (1983) 593
57. Brandi A., Cicchi S., Cordero F.M., Frignoli R., Goti A., Picasso S., and Vogel P. J. Org. Chem. 60 (1995) 6806