Skeletal rearrangement of seven-membered iminosugars: Synthesis of (-)-adenophorine, (-)-1-epi-adenophorine and derivatives and evaluation as glycosidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 16, 2013, Pages 4803-4812

  Mondon, Martine ^a   Lecornué, Frédéric ^a   Guillard, Jérôme ^a   Nakagawa, Shinpei ^b   Kato, Atsushi ^b   Blériot, Yves ^a  

^a UNIVERSITÉ DE POITIERS   (France)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Adenophorine; Azepane; Glycosidase inhibition; Iminosugar; Natural product

Indexed keywords

1 EPIADENOPHORINE; 2 ETHYL 6 (HYDROXYMETHYL)PIPERIDINE 3,4,5 TRIOL; 2 ETHYLAZEPAN 3,4,5,6 TETRAOL; 2 HYDROXYMETHYL 6 PROPYLPIPERIDINE 3,4,5 TRIOL; 2 PROPYLAZEPAN 3,4,5,6 TETRAOL; 2,6 DIETHYLPIPERIDINE 3,4,5 TRIOL; ADENOPHORINE; ALPHA GALACTOSIDASE; ALPHA GLUCOSIDASE; ALPHA LEVO FUCOSIDASE; ALPHA MANNOSIDASE; BETA GALACTOSIDASE; BETA GLUCOSIDASE; BETA GLUCURONIDASE; BETA MANNOSIDASE; DIALLYLZINC; GLUCAN 1,4 ALPHA GLUCOSIDASE; GLYCOSIDASE INHIBITOR; IMINOSUGAR; ORGANOALUMINUM DERIVATIVE; ORGANOCERIUM COMPOUND; ORGANOLITHIUM COMPOUND; ORGANOMAGNESIUM COMPOUND; ORGANOMETALLIC COMPOUND; ORGANOZINC COMPOUND; TREHALASE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYMATIC ASSAY; ENZYME INHIBITION; STAUDINGER REACTION; WITTIG REACTION;

ADENOPHORINE; AZEPANE; GLYCOSIDASE INHIBITION; IMINOSUGAR; NATURAL PRODUCT;

ALKYLATION; ALPHA-L-FUCOSIDASE; ANIMALS; ASPERGILLUS NIGER; AZA COMPOUNDS; ENZYME INHIBITORS; GLYCOSIDE HYDROLASES; IMINO SUGARS; ORYZA SATIVA; PROTEIN BINDING; RATS; SACCHAROMYCES CEREVISIAE; STEREOISOMERISM;

EID: 84880571680     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.03.035     Document Type: Article

References (48)

1. O.R. Martin, and P. Compain Iminosugars: From synthesis to therapeutic applications 2007 Wiley-VCH Weinheim
2. G.S. Jacob Curr. Opin. Struct. Biol. 5 1995 605
3. P.L. McCormack, and K.L. Goa Drugs 63 2003 2427
4. G. Horne, and F.X. Wilson Prog. Med. Chem. 50 2011 135
5. G. Horne, F.X. Wilson, J. Tinsley, D.H. Williams, and R. Storer Drug Discovery Today 16 2011 107
6. C. Norez, S. Noel, M. Wilke, M. Bijvelds, H. Jorna, P. Melin, H. DeJonge, and F. Becq FEBS Lett. 580 2006 2081
7. B. Lubamba, J. Lebacq, P. Lebecque, R. Vanbever, A. Leonard, P. Wallemacq, and T. Leal Am. J. Respir. Crit. Care Med. 179 2009 1022
8. R. Khanna, R. Soska, Y. Lun, J. Feng, M. Frascella, B. Young, N. Brignol, L. Pellegrino, S.A. Sitaraman, R.J. Desnick, E.R. Benjamin, D.J. Lockhart, and K.J. Valenzano Mol. Ther. 18 2010 23
9. T. Wennekes, T.J. Boltje, W.E. Donker-Koopman, B. Kuijper, G.A. van der Marel, A. Strijland, C.P. Verhagen, J.M.F.G. Aerts, and H.S. Overkleeft Eur. J. Org. Chem. 10 2010 1258
10. W. Schönemann, E. Galienne, P. Compain, K. Ikeda, N. Asano, and O.R. Martin Bioorg. Med. Chem. 18 2010 2645
11. K.T. Weber, D. Hammache, J. Fantini, and B. Ganem Bioorg. Med. Chem. Lett. 10 2000 1011
12. H.-J. Wu, C.-W. Ho, T.-P. Ko, S.D. Popat, C.-H. Lin, and A.H.-J. Wang Angew. Chem., Int. Ed. 49 2010 337
13. W. Yu, T. Gill, L. Wang, L.Y. Du, H. Ye, X. Qu, J.-T. Guo, A. Cuconati, K. Zhao, T.M. Block, X. Xu, and J. Chang J. Med. Chem. 55 2012 6061
14. N. Asano, M. Nishida, H. Kizu, K. Matsui, A.A. Watson, and R.J. Nash J. Nat. Prod. 60 1997 98
15. N. Asano, A. Kato, M. Miyauchi, H. Kizu, Y. Kameda, A.A. Watson, R.J. Nash, and G.W.J. Fleet J. Nat. Prod. 61 1998 625
16. K. Yasuda, H. Kizu, T. Yamashita, Y. Kameda, A. Kato, R.J. Nash, G.W.J. Fleet, R.J. Molyneux, and N. Asano J. Nat. Prod. 65 2002 198
17. T. Yamashita, K. Yasuda, H. Kizu, Y. Kameda, A.A. Watson, R.J. Nash, G.W.J. Fleet, and N. Asano J. Nat. Prod. 65 2002 1875
18. N. Asano, K. Ikeda, M. Kasahara, Y. Arai, and H. Kizu J. Nat. Prod. 67 2004 846
19. A. Kato, N. Kato, I. Adachi, J. Hollinshead, G.W.J. Fleet, C. Kuriyama, K. Ikeda, N. Asano, and R.J. Nash J. Nat. Prod. 70 2007 993
20. K. Ikeda, M. Takahashi, M. Nishida, M. Miyauchi, H. Kizu, Y. Kameda, M. Arisawa, A.A. Watson, R.J. Nash, G.W.J. Fleet, and N. Asano Carbohydr. Res. 323 2000 73
21. M.S.M. Pearson, M. Evain, M. Mathé-Allainmat, and J. Lebreton Eur. J. Org. Chem. 2007 4888
22. M.A.T. Maughan, I.G. Davies, T.D.W. Claridge, S. Courtney, P. Hay, and B.G. Davis Angew. Chem., Int. Ed. 42 2003 3788
23. D. D'Alonzo, A. Guaragna, and G. Palumbo Curr. Med. Chem. 16 2009 473
24. S.F. Jenkinson, G.W.J. Fleet, R.J. Nash, Y. Koike, I. Adachi, A. Yoshihara, K. Morimoto, K. Izumori, and A. Kato Org. Lett. 13 2011 4064
25. P. Compain, V. Chaignault, and O. Martin R Tetrahedron: Asymmetry 20 2009 672
26. C.R. Johnson, A. Golebiowski, H. Sundram, M.W. Miller, and R.L. Dwaihy Tetrahedron Lett. 36 1995 653
27. T. Granier, and A. Vasella Helv. Chim. Acta 81 1998 865
28. T. Fuchss, H. Streicher, and R.R. Schmidt Liebigs Ann. Recl. 1997 1315
29. B.G. Davis, M.A.T. Maughan, T.M. Chapman, R. Villard, and S. Courtney Org. Lett. 4 2002 103
30. A. Peer, and A. Vasella Helv. Chim. Acta 82 1999 1044
31. F. Marcelo, Y. He, S.A. Yuzwa, L. Nieto, J. Jiménez-Barbero, M. Sollogoub, D.J. Vocadlo, G.J. Davies, and Y. Blériot J. Am. Chem. Soc. 131 2009 5390
32. H. Li, T. Liu, Y. Zhang, S. Favre, C. Bello, P. Vogel, T.D. Butters, N.G. Oikonomakos, J. Marrot, and Y. Blériot ChemBioChem 9 2008 253
33. H. Li, Y. Blériot, C. Chantereau, J.-M. Mallet, M. Sollogoub, Y. Zhang, E. Rodriguez-Garcia, P. Vogel, J. Jiménez-Barbero, and P. Sinaÿ Org. Biomol. Chem. 2 2004 1492
34. T. Liu, Y. Zhang, and Y. Blériot Synlett 2007 905
35. M. Mondon, N. Fontelle, J. Désiré, F. Lecornué, J. Guillard, J. Marrot, and Y. Blériot Org. Lett. 14 2012 870
36. W.R. Kobertz, C.R. Bertozzi, and M.D. Bednarski J. Org. Chem. 61 1996 1894
37. T.K. Chakraborty, S. Ghosh, S. Jayaprakash, J.A.R.P. Sharma, V. Ravikanth, P.V. Diwan, R. Nagaraj, and A.C. Kunwar J. Org. Chem. 65 2000 6441
38. R. Bloch Chem. Rev. 98 1998 1407
39. D. Enders, and U. Reinhold Tetrahedron: Asymmetry 8 1997 1895
40. A.G. Steinig, and D.M. Spero Org. Prep. Proc. Int. 32 2000 205
41. for organocerium derivatives see: G. Bartoli, E. Marcantoni, M. Marcolini, and L. Sambri Chem. Rev. 110 2010 6104
42. S. Cutri, M. Bonin, L. Micouin, H.-P. Husson, and A. Chiaroni J. Org. Chem. 68 2003 2645
43. L. Cipolla, L. Lay, F. Nicotra, C. Pangrazio, and L. Panza Tetrahedron 51 1995 4679
44. V. Chagnault, P. Compain, K. Lewinski, K. Ikeda, N. Asano, and O.R. Martin J. Org. Chem. 74 2009 3179
45. T. Tite, A. Tsimilaza, M.-C. Lallemand, F. Tillequin, P. Leproux, F. Libot, and H.-P. Husson Eur. J. Org. Chem. 2006 863
46. K. Afarinkia, A. Bahar, and J. Neuss Synlett 2007 1375
47. F. Moris-Varas, X.-H. Qian, and C.-H. Wong J. Am. Chem. Soc. 118 1996 7647
48. The organocerium reagents were prepared using Imamoto procedure: Takeda, N.; Imamoto, T. Org. Synth. Coll. 2004, 10, 200.