Synthesis of multibranched australine derivatives from reducing castanospermine analogues through the amadori rearrangement of gem -diamine intermediates: Selective inhibitors of β-glucosidase

Journal of Organic Chemistry

Volumn 79, Issue 23, 2014, Pages 11722-11728

  Sánchez Fernández, Elena M ^a   Álvarez, Eleuterio ^b   Ortiz Mellet, Carmen ^a   García Fernández, José M ^b  

^a UNIVERSITY OF SEVILLE   (Spain)

^b CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITION;

AMADORI REARRANGEMENTS; ANOMERIC EFFECT; BETA-GLUCOSIDASE; CASTANOSPERMINE; DIASTEREOMERS; GAUCHER DISEASE; ONE-POT SYNTHESIS; SELECTIVE INHIBITORS;

AMINES;

1 DEOXY 5 OCTYLAMINO 3 OCTYLIMINO 2 OXACASTANOSPERMINE; 1 DEOXY 6 EPI 5 HYDROXY 3 OCTYLIMINO 2 OXACASTANOSPERMINE; 1 DEOXY 6 EPI 5 OCTYLAMINO 2 OXA 3 OXOCASTANOSPERMINE; 1 O ACETYL 2,3 O ISOPROPYLIDENE 5 DEOXY 5 (N' OCTYLUREIDO) ALPHA DEXTRO MANNOFURANOSE; 3,8 DIBUTYLAMINO 7,8 DIDEOXY 5 OCTYLIMINO 6 OXA 3 EPI AUSTRALINE; 4 [1' O ACETYL 2',3' O ISOPROPYLIDENE LEVO ERYTHROFURANOS 4' YL] 2 OCTYLAMINO 2 OXAZOLINE; 7,8 DIDEOXY 3 HYDROXY 8 OCTYLAMINO 5 OCTYLIMINO 6 OXA 3 EPIAUSTRALINE; 7,8 DIDEOXY 3,8 DIDODECYLAMINO 5 OCTYLIMINO 6 OXA 3 EPI AUSTRALINE; 7,8 DIDEOXY 3,8 DIOCTYLAMINO 5 OCTYLIMINO 6 OXA 3 EPI AUSTRALINE; 7,8 DIDEOXY 8 DODECYLAMINO 3 HYDROXY 5 OCTYLIMINO 6 OXA 3 EPI AUSTRALINE; 8 BUTYLAMINO 7,8 DIDEOXY 3 HYDROXY 5 OCTYLIMINO 6 OXA 3 EPI AUSTRALINE; AUSTRALINE; AUSTRALINE DERIVATIVE; BETA GLUCOSIDASE INHIBITOR; CASTANOSPERMINE DERIVATIVE; DIAMINE DERIVATIVE; GLYCOSIDASE INHIBITOR; INDOLIZIDINE DERIVATIVE; PYRROLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG; BETA GLUCOSIDASE; CASTANOSPERMINE; CHAPERONE; DIAMINE; ENZYME INHIBITOR; INDOLIZINE DERIVATIVE; PYRROLIZIDINE ALKALOID;

ALMOND; AMADORI REARRANGEMENT; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATTLE; CHIRALITY; COMPETITIVE INHIBITION; CONFORMATION; DRUG SYNTHESIS; ESCHERICHIA COLI; GAUCHER DISEASE; HYDROGEN BOND; ISOMERIZATION; NUCLEAR OVERHAUSER EFFECT; NUCLEOPHILICITY; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION TIME; REDUCTION; RING OPENING; X RAY DIFFRACTION; YEAST; ANTAGONISTS AND INHIBITORS; BIOCHEMISTRY; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; SYNTHESIS;

BETA-GLUCOSIDASE; BIOCHEMICAL PROCESSES; DIAMINES; ENZYME INHIBITORS; GAUCHER DISEASE; HUMANS; INDOLIZIDINES; INDOLIZINES; MOLECULAR CHAPERONES; MOLECULAR STRUCTURE; PYRROLIZIDINE ALKALOIDS;

EID: 84916238664     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5025283     Document Type: Article

References (55)

1. Nash, R. J.; Kato, A.; Yu, C.-Y.; Fleet, G. W. J. Future Med. Chem. 2011, 3, 1531-1521
2. Home, G.; Francis, X.; Tinsley, J.; Williams, D. H.; Storer, R. Drug Discovery Today 2011, 16, 107-118
3. Wrodnigg, T. M.; Steiner, A. J.; Ueberbacher, B. J. Anti-Cancer Agents Med. Chem. 2008, 8, 77-85
4. Bhat, C.; Tilve, S. G. RSC Adv. 2014, 4, 5405-5452
5. Compain, P. Synlett 2014, 1215-1240
6. Lahiri, R.; Ansari, A. A.; Vankar, Y. D. Chem. Soc. Rev. 2013, 42, 5102-5118
7. Dragutan, I.; Dragutan, V.; Demonceau, A. RSC Adv. 2012, 2, 719-736
8. Stocker, B. L.; Dangerfield, E. M.; Win-Mason, A. L.; Haslett, G. W.; Timmer, M. S. M. Eur. J. Org. Chem. 2010, 1615-1637
9. Laborda, P.; Sayago, F. J.; Cativiela, C.; Parella, T.; Joglar, J.; Clapés, P. Org. Lett. 2014, 16, 1422-1425
10. Du-a-man, S.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakort, M. Eur. J. Org. Chem. 2014, 1708-1715
11. Abels, F.; Lindemann, C.; Schneider, C. Chem.-Eur. J. 2014, 20, 1964-1979
12. Crabtree, E. V.; Martinez, R. F.; Nakagawa, S.; Adachi, I.; Kato, A.; Fleet, G. W. J.; Glawar, A. F. G. Org. Biomol. Chem. 2014, 12, 3932-3943
13. Malik, G.; Ferry, A.; Guinchard, X.; Crestell, T.; Crich, D. Chem.-Eur. J. 2013, 19, 2168-2179
14. Malik, M.; Witkowski, G.; Ceborska, M.; Jarosz, S. Org. Lett. 2013, 15, 6214-6217
15. Dahnd, V.; Draper, J. A.; Moore, J.; Britton, R. Org. Lett. 2013, 15, 1914-1917
16. Davies, S. G.; Figuccia, A. L. A.; Fletcher, A. M.; Roberts, P. M.; Thomson, J. E. Org. Lett. 2013, 15, 2042-2045
17. Parmeggiani, C.; Cardona, F.; Giusti, L.; Reissig, H.-J; Goti, A. Chem.-Eur. J. 2013, 19, 10595-10604
18. Yu, Y.; Mena-Barragán, T.; Higaki, K.; Johnson, J. L.; Drury, J. E.; Lieberman, R. L.; Nakasone, N.; Ninomiya, H.; Tsukimura, T.; Sakuraba, H.; Suzuki, Y.; Namba, E.; Ortiz Mellet, C.; García Fernández, C.; Ohno, K. ACS Chem. Biol. 2014, 9, 1460-1469
19. Aguilar-Moncayo, M.; Takai, T.; Higaki, K.; Mena-Barragán, T.; Hirano, Y.; Yura, K.; Li, L.; Yu, Y.; Ninomiya, H.; García-Moreno, M. I.; Ishii, S.; Sakakibara, Y.; Ohno, K.; Namba, E.; Ortiz Mellet, C.; García Fernández, J. M.; Suzuki, Y. Chem. Commun. 2011, 48, 6514-6516
20. Andrews, J. S.; Weimar, T.; Frandsen, T. P.; Svensson, B.; Pinto, B. M. J. Am. Chem. Soc. 1995, 117, 10799-10804
21. Kavlekar, L. M.; Kuntz, D. A.; Wen, X.; Johnston, B. D.; Svensson, B.; Rose, D. R.; Pinto, B. M. Tetrahedron: Asymmetry 2005, 16, 1035-1046
22. Cumpstey, I.; Ramstadius, C.; Borbas, K. E.; Alonzi, D. S.; Butters, T. D. Bioorg. Med. Chem. 2011, 19, 5219-5223
23. Shing, T. K. M.; Cheng, H. M.; Wong, W. F.; Kwong, C. S. K.; Li, J.; Lau, C. B. S.; Leung, P. S.; Cheng, C. H. K. Org. Lett. 2008, 10, 3145-3149
24. Siriwardena, A.; Sonawane, D. P.; Bande, O. P.; Markad, P. R.; Yonekawa, S.; Tropak, M. B.; Ghosh, S.; Chopade, B. A.; Mahuran, D. J.; Dhavale, D. D. J. Org. Chem. 2014, 79, 4398-4404
25. Senthilkumar, S.; Prasad, S. S.; Kumar, P. S.; Baskaran, S. Chem. Commun. 2014, 50, 1549-1551
26. Biela-Banas, A.; Gallienne, E.; Front, S.; Martin, O. R. Tetrahedron Lett. 2014, 55, 838-841
27. Zoidi, M.; Muller, B.; Torvisco, A.; Tysoe, C.; Benazza, M.; Siriwardena, A.; Withers, S. G.; Wrodnigg, T. Bioorg. Med. Chem. Lett. 2014, 24, 2777-2780
28. Santana, A. G.; Paz, N. R.; Francisco, C. G.; Suárez, E.; González, C. J. Org. Chem. 2013, 78, 7527-7543
29. Mondon, M.; Fontelle, N.; Désiré, J.; Lecornue, F.; Guillard, J.; Marrot, J.; Blériot, Y. Org. Lett. 2012, 14, 870-873
30. Wennekes, T.; van den Berg, R. J. H. N.; Boltje, T. J.; Donker-Koopman, W. E.; Kuijper, B.; van der Marel, G. A.; Strijland, A.; Verhagen, C. P.; Aerts, J. M. F. G.; Overkleeeft, H. S. Eur. J. Org. Chem. 2010, 1258-1283
31. Compain, P.; Chagnault, V.; Martin, O. R. Tetrahedron: Asymmetry 2009, 20, 672-711
32. Wennekes, T.; van der Berg, R. J. B. H. N.; Boot, R. G.; van der Marel, G. A.; Overkleeft, H. S.; Aerts, J. M. F. G. Angew. Chem., Int. Ed. 2009, 48, 8848-8869
33. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M. Chem. Commun. 1997, 1969-1970
34. Rísquez-Cuadro, R.; García Fernández, J. M.; Nierengarten, J.-F.; Ortiz Mellet, C. Chem.-Eur. J. 2013, 19, 16791-16803
35. Sánchez-Fernández, E. M.; Rísquez-Cuadro, R.; Chasseraud, M.; Ahidouch, A.; Ortiz Mellet, C.; Ouadid-Ahidouch, H.; García Fernández, J. M. Chem. Commun. 2010, 46, 5328-5330
36. Allan, G.; Ahidouch, A.; Sánchez-Fernández, E. M.; Rísquez-Cuadro, R.; García Fernandez, J. M.; Ortiz Mellet, C.; Ouadid-Ahidouch, H. PLoS One 2013, 8, e76411
37. Wrodnigg, T. M.; Eder, B. Top. Curr. Chem. 2001, 215, 115-152
38. Frongia, A.; Secci, F.; Capitta, F.; Piras, P. P.; Sanna, M. L. Chem. Commun. 2013, 49, 8812-8814
39. Gallas, K.; Pototschnig, G.; Adanitsch, F.; Stütz, A. E.; Wrodnigg, T. M. Beilstein J. Org. Chem. 2012, 8, 1619-1629
40. Hricovíniová, Z. Tetrahedron: Asymmetry 2010, 2238-2243
41. Wrodnigg, T. M.; Kartusch, C.; Illaszewicz, C. Carbohydr. Res. 2008, 343, 2057-2066
42. Hotchkiss, D. J.; Soengas, R.; Booth, K. V.; Weymouth-Wilson, A. C.; Eastwick-Field, V.; Fleet, G. W. J. Tetrahedron Lett. 2007, 48, 517-520
43. García-Moreno, M. I.; Díaz-Pérez, P.; Ortiz Mellet, C.; García Fernández, J. M. Chem. Commun. 2002, 848-849
44. Luan, Z.; Higaki, K.; Aguilar-Moncayo, M.; Ninomiya, H.; Ohno, K.; García-Moreno, M. I.; Ortiz Mellet, C.; García Fernández, J. M.; Suzuki, Y. ChemBioChem 2009, 10, 2780-2792
45. Díaz Pérez, V. M.; García-Moreno, M. I.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. J. Org. Chem. 2000, 65, 136-143
46. Díaz Pérez, P.; García-Moreno, M. I.; Ortiz Mellet, C.; García Fernández, J. M. Eur. J. Org. Chem. 2005, 2903-2913
47. Asensio, J. L.; Cañada, F. J.; García-Herrero, A.; Murillo, M. T.; Fernández-Mayoralas, A.; Johns, B. A.; Kozak, J.; Zhu, Z. Z.; Johnson, C. R.; Jiménez-Barbero, J. J. Am. Chem. Soc. 1999, 121, 11318-11329
48. Suzuki, H.; Ohto, U.; Higaki, K.; Mena-Barragán, T.; Aguilar-Moncayo, M.; Ortiz Mellet, C.; Namba, E.; García Fernández, J. M.; Suzuki, Y.; Shimizu, T. J. Biol. Chem. 2014, 289, 14560-14568
49. Kato, A.; Kano, E.; Adachi, I.; Molineux, R. J.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Wormald, M. J.; Kizu, H.; Ikeda, K.; Asano, N. Tetrahedron: Asymmetry 2003, 14, 325-331
50. Castilla, J.; Rísquez, R.; Cruz, D.; Higaki, K.; Namba, E.; Ohno, K.; Suzuki, Y.; Díaz, Y.; Ortiz Mellet, C.; García Fernández, J. M.; Castillón, S. J. Med. Chem. 2012, 58, 6857-6865
51. In a preliminary test, compounds 12b, 12c, 13a, and 13b exhibited inhibition curves toward human β-glucocerebrosidase that matched that obtained for Ambroxol, a non-iminosugar type inhibitor in preclinical studies for chaperone therapy. See: Suzuki, Y. Brain Dev. 2013, 6, 515-518
52. APEX2; Bruker AXS Inc.: Madison, WI, 2007.
53. SADABS; Bruker AXS Inc.: Madison, WI, 2001.
54. Burla, M. C.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; Giacovazzo, C.; Poliori, G.; Spagna, R. J. Appl. Crystallogr. 2003, 36, 1103
55. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122