Building multivalent iminosugar-based ligands on calixarene cores via nitrone cycloadditions

Journal of Organic Chemistry

Volumn 77, Issue 16, 2012, Pages 6980-6988

  Cardona, Francesca ^a   Isoldi, Giovanni ^a   Sansone, Francesco ^b   Casnati, Alessandro ^b   Goti, Andrea ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALIX[4]ARENES; CALIXARENES; CYCLOADDITION REACTION; CYCLOADDITIONS; FUNCTIONALIZED; IMINOSUGARS; NEOGLYCOCONJUGATES; NITRONES;

CYCLOADDITION; SCAFFOLDS;

CARBOHYDRATES;

25,26,27,28 TETRAKIS[[4,5 BIS(BENZYLOXY) 6 [(BENZYLOXY)METHYL]HEXAHYDROPYRROLO[1,2 B]ISOXAZOL 2 YL]METHOXY]CALIX[4]ARENE; 26,28 BIS[3 (3,4 DIBENZYLOXY 2 BENZYLOXYMETHYL PYRROLIDIN 5 ) 2 HYDROXYPROPYL] 25,27 DIHYDROXYCALIX[4]ARENE; 26,28 BIS[[4,5 BIS(BENZYLOXY) 6 [(BENZYLOXY)METHYL] HEXAHYDROPYRROLO[1,2-B]ISOXAZOL 2 YL]METHOXY] 25,27 DIHYDROXY CALIX[4]ARENE; 5,11,17,23 TETRAKIS[[4,5 BIS(BENZYLOXY) 6 [(BENZYLOXY)METHYL]HEXAHYDROPYRROLO[1,2 B]ISOXAZOL 2 YL]METHYL] 25,26,27,28 TETRAPROPOXY CALIX[4]ARENE; 5,17 BIS[3 (3,4 DIBENZYLOXY 2 BENZYLOXYMETHYL PYRROLIDIN 5) 2 HYDROXYPROPYL] 25,26,27,28 TETRAPROPOXY CALIX[4]ARENE; 5,17 BIS[[4,5 BIS(BENZYLOXY) 6 [(BENZYLOXY)METHYL]HEXAHYDROPYRROLO[1,2 B]ISOXAZOL 2 YL]METHYL] 25,26,27,28 TETRAPROPOXY CALIX[4]ARENE; CALIXARENE; IMINOSUGAR; NITRONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; STEREOCHEMISTRY; SYNTHESIS;

CALIXARENES; CYCLOADDITION REACTION; GLYCOCONJUGATES; IMINO SUGARS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITROGEN OXIDES; STEREOISOMERISM;

EID: 84865211574     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301155p     Document Type: Article

References (54)

1. Lis, H.; Sharon, N. Chem. Rev. 1998, 98, 637-674
2. Ambrosi, M.; Cameron, N. R.; Davis, B. G. Org. Biomol. Chem. 2005, 3, 1593-1608
3. Gabius, H.-J.; André, S.; Kaltner, H.; Siebert, H.-C. Biochim. Biophys. Acta, Gen. Subj. 2002, 1572, 165-177
4. Lee, Y. C.; Lee, T. R. Acc. Chem. Res. 1995, 28, 321-327
5. Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754-94
6. Lundquist, J. J.; Toone, E. J. Chem. Rev. 2002, 102, 555-578
7. Choi, S. K. Synthetic Multivalent Molecules; Wiley-VCH: New York, 2004.
8. Chabre, Y. M.; Roy, R. Adv. Carbohydr. Chem. Biochem. 2010, 63, 165-393
9. Deniaud, D.; Julienne, K.; Gouin, S. G. Org. Biomol. Chem. 2011, 9, 966-979
10. Baldini, A. L.; Casnati, A.; Sansone, F.; Ungaro, R. Chem. Soc. Rev. 2007, 36, 254-266
11. Kiessling, L. L.; Gestwicki, J. E.; Strong, L. E. Angew. Chem., Int. Ed. 2006, 45, 2348-2368
12. Imberty, A.; Chabre, Y. M.; Roy, R. Chem.-Eur. J. 2008, 14, 7490-7499
13. Pieters, R. J. Org. Biomol. Chem. 2009, 7, 2013-2025
14. Kitov, P. I.; Sadowska, J. M.; Mulvey, G.; Armstrong, G. D.; Ling, H.; Pannu, N. S.; Read, R. J.; Bundle, D. R. Nature 2000, 403, 669-672
15. Gómez-García, M.; Benito, J. M.; Rodríguez-Lucena, D.; Yu, J.-X.; Chmurski, K.; Ortiz Mellet, C.; Gutiérrez Gallego, R.; Maestre, A.; Defaye, J.; García Fernández, J. M. J. Am. Chem. Soc. 2005, 127, 7970-7971
16. Gómez-García, M.; Benito, J. M.; Gutiérrez Gallego, R.; Maestre, A.; Ortiz Mellet, C.; García Fernández, J. M.; Jiménez Blanco, J. L. Org. Biomol. Chem. 2010, 8, 1849-1860
17. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749-752
18. Lohse, A.; Jensen, K. B.; Lundgren, K.; Bols, M. Bioorg. Med. Chem. 1999, 7, 1965-1971
19. Wennekes, T.; van den Berg, R. J. B. H. N.; Bonger, K. M.; Donker-Koopman, W. E.; Ghisaidoobe, A.; van der Marel, G. A.; Strijland, A.; Aerts, J. M. F. G.; Overkleeft, H. S. Tetrahedron: Asymmetry 2009, 20, 836-846
20. Diot, J.; García-Moreno, M. I.; Gouin, S. G.; Ortiz Mellet, C.; Haupt, K.; Kovensky, J. Org. Biomol. Chem. 2009, 7, 357-363
21. Compain, P.; Decroocq, C.; Iehl, J.; Holler, M.; Hazelard, D.; Mena Barragán, T.; Ortiz Mellet, C.; Nierengarten, J.-F. Angew. Chem., Int. Ed. 2010, 122, 5889-5892
22. Decroocq, C.; Rodríguez-Lucena, D.; Russo, V.; Mena Barragán, T.; Ortiz Mellet, C.; Compain, P. Chem.-Eur. J. 2011, 17, 13825-13831
23. Compain, P.; Martin, O. R. Iminosugars: from Synthesis to Therapeutic Applications; Wiley VCH: New York, 2007.
24. André, S.; Grandjean, C.; Gautier, F.-M.; Bernardi, S.; Sansone, F.; Gabius, H.-J.; Ungaro, R. Chem. Commun. 2011, 47, 6126-6127
25. Galante, S.; Geraci, C.; Sciuto, S.; Campo, V. L.; Carvalho, I.; Sesti-Costa, R.; Guedes, P. M. M.; Silva, J. S.; Hill, L.; Nepogodiev, S. A.; Field, R. A. Tetrahedron 2011, 67, 5902-5912
26. Moni, L.; Rossetti, S.; Scoponi, M.; Marra, A.; Dondoni, A. Chem. Commun. 2010, 46, 475-477
27. Fulton, D. A.; Stoddart, F. F. Bioconjugate Chem. 2001, 12, 655-672
28. Casnati, A.; Sansone, F.; Ungaro, R. Acc. Chem. Res. 2003, 36, 246-254
29. Baldini, L.; Casnati, A.; Sansone, F.; Ungaro, R. Chem. Soc. Rev. 2007, 36, 254-266
30. Dondoni, A.; Marra., A. Chem. Rev. 2010, 110, 4949-4977
31. Sansone, F.; Baldini, L.; Casnati, A.; Ungaro, R. New J. Chem. 2010, 34, 2715-2728
32. Dondoni, A. Org. Biomol. Chem. 2010, 8, 3366-3385
33. Sansone, F.; Rispoli, G.; Casnati, A.; Ungaro, R. Multivalent Glycocalixarenes. In Synthesis and Biological Applications of Glycoconjugates; Renaudet, O.; Spinelli, N., Eds.; Bentham Science Publishers: Sharjah, United Arab Emirates, 2011; pp 36-63.
34. Tarbell, D. S.; Kincaid, J. F. J. Am. Chem. Soc. 1940, 62, 728-731
35. Curtin, D. Y.; Crawford, R. J.; Wilhelm, M. J. Am. Chem. Soc. 1958, 80, 1391-1397
36. Hansen, H.-J. Helv. Chim. Acta 1977, 60, 2007-2033
37. Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem. 1993, 58, 5274-5275
38. Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806-6812
39. Cardona, F.; Goti, A.; Picasso, S.; Vogel, P.; Brandi, A. J. Carbohydr. Chem. 2000, 19, 585-601
40. For a review, see: Brandi, A.; Cardona, F.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem.-Eur. J. 2009, 15, 7808-7821
41. Cardona, F.; Faggi, E.; Liguori, F.; Cacciarini, M.; Goti, A. Tetrahedron Lett. 2003, 44, 2315-2318
42. Bonaccini, C.; Chioccioli, M.; Parmeggiani, C.; Cardona, F.; Lo, Re, D.; Soldaini, G.; Vogel, P.; Bello, C.; Goti, A.; Gratteri, A. Eur. J. Org. Chem. 2010, 5574-5585
43. Cardona, F.; Goti, A.; Parmeggiani, C.; Parenti, P.; Forcella, M.; Fusi, P.; Cipolla, L.; Roberts, S. M.; Davies, G. J.; Gloster, T. M. Chem. Commun. 2010, 46, 2629-2631
44. Dondoni, A.; Kleban, M.; Hu, X.; Marra, A.; Banks, H. D. J. Org. Chem. 2002, 67, 4722-4733
45. van Loon, J.-D.; Arduini, A.; Coppi, L.; Verboom, W.; Pochini, A.; Ungaro, R.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1990, 55, 5639-5646
46. Gutsche, C. D.; Dhawan, B.; Levine, J. A.; No, K. H.; Bauer, L. J. Tetrahedron 1983, 39, 409-426
47. Gutsche, C. D. Calixarenes: An Introduction; Royal Society of Chemistry: Cambridge, U.K., 2008.
48. Böhmer, V. Angew. Chem., Int. Ed. 1995, 34, 713-745
49. Casnati, A. Gazz. Chim. Ital. 1997, 127, 637-649
50. Casnati, A.; Ferdani, R.; Pochini, A.; Ungaro, R. J. Org. Chem. 1997, 62, 6236-6239
51. Casas, C. P.; Yamamoto, H.; Yamato, T. J. Chem. Res. 2005, 11, 694-696
52. Luo, J.; Shen, L.-C.; Chung, W.-S. J. Org. Chem. 2010, 75, 464-467
53. Cardona, F.; Parmeggiani, C.; Faggi, E.; Bonaccini, C.; Gratteri, P.; Sim, L.; Gloster, T. M.; Roberts, S.; Davies, G. J.; Rose, D. R. Chem.-Eur. J. 2009, 15, 1627-1636
54. Parmeggiani, C.; Martella, D.; Cardona, F.; Goti, A. J. Nat. Prod. 2009, 72, 2058-2060