On the synthesis of new amphiphilic entities by the succinic coupling of β-cyclodextrins to calixarenes

Canadian Journal of Chemistry

Volumn 83, Issue 5, 2005, Pages 493-498

  Jankowski, Christopher K ^a   Arseneau, Sébastien ^a   Blu, Jérome ^b   Mauclaire, Laurent ^b   Aychet, Nicolas ^b  

^a UNIVERSITÉ DE MONCTON   (Canada)

^b Departement de Recherche Sur l'Etat Condense Les Atomes et Les Molecules (DRECAM)   (France)

Author keywords

cyclodextrin calix 4 arene coupling; Aminosuccinate CD; Aminosuccinate calix 4 arene; Calix 4 arene biscrown 6; Octyloxy calix 4 arene monocrown 6

Indexed keywords

AMINES; DERIVATIVES; MOLECULAR STRUCTURE; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

AMPHIPHILIC ENTITIES; CALIXARENES; NOVEL MOLECULES; SUCCINIC COUPLINGS;

CRACKING (CHEMICAL);

6' DEOXY 6' AMINO BETA CYCLODEXTRIN; AMPHOPHILE; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; BIS CROWN 6 CALIX[4]ARENE; CALIXARENE; CROWN ETHER DERIVATIVE; DI N OCTYL CALIX[4]ARENE CROWN 6; DIAMIDE; SUCCINIC ACID; TETRAAMINOCALIX[4]ARENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COUPLING REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 22844437758     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-070     Document Type: Article

References (31)

1. N. Funasaki, S. Ishikawa, and S. Neya. J. Phys. Chem. B, 108, 9593 (2004).
2. S. Daoud-Mahammed, P. Couvreur, C. Amiel, M. Besnard, M. Appel, and R. Gref. J. Drug Deliv. Sci. Tec. 14, 51 (2004).
3. J. Lin, C. Creminon, B. Perly, and F. Djedaïni-Pilard. J. Chem. Soc. Perkin Trans. 2, 2639 (1998).
4. J.J. Michels, J. Huskens, J.F.J. Engbersen, and D.N. Reinhoudt. Langmuir, 16, 4864 (2000).
5. D.A. Fulton and J.F. Stoddart. Bioconjugate Chem. 12, 655 (2001).
6. I. Higler, P. Timmerman, W. Verboom, and D.N. Reinhoudt. Eur. J. Org. Chem. 2689 (1998).
7. W. Sliwa, T. Girek, and J.J. Koziol. Curr. Org. Chem. 8, 1445 (2004).
8. J.J. Michels, R. Fiammengo, P. Timmerman, J. Huskens, and D.N. Reinhoudt. J. Inclusion Phenom. Macrocyclic Chem. 41, 163 (2001).
9. J.J. Michels, M.W.P.L. Baars, E.W. Meijer, J. Huskens, and D.N. Reinhoudt. J. Chem. Soc. Perkin Trans. 2, 1914 (2000).
10. Y. Liu, Y. Chen, L. Li, G. Huang, C.C. You, H.Y. Zhang, T. Wada, and Y. Inoue. J. Org. Chem. 66, 7209 (2001).
11. N. Kuhnert and A. Le-Gesley. Chem. Commun. 2426 (2003).
12. R. Zadmard, M. Junkers, T. Schrader, T. Grawe, and A. Kraft. J. Org. Chem. 68, 6511 (2003).
13. M.R. de Jong, J. Huskens, and D.N. Reinhoudt. Chem. Eur. J. 7, 4164 (2001).
14. C.K. Jankowski, J.F. Dozol, F. Allain, J.C. Tabet, R. Ungaro, A. Casnati, J. Vicens, A. Asfari, and J. Boivin. Pol. J. Chem. 76, 701 (2002).
15. C. Péan, C. Créminon, A. Wijkhuisen, J. Grassi, P. Guenot, P. Jéhan, J.P. Dalbiez, B. Perly, and F. Djedaïni-Pilard. J. Chem. Soc. Perkin Trans. 2, 853 (2000).
16. R.C. Petter, J.S. Salek, C.T. Sikorski, G. Kumaravel, and F.T. Lin. J. Am. Chem. Soc. 112, 3860 (1990).
17. H.S. Byun, N. Zhong, and R. Bittman. Org. Synth. 77, 225 (2000).
18. F. Djedaïni-Pilard, F. Désalos, and B. Perly. Tetrahedron Lett. 34, 2457 (1993).
19. C.K. Jankowski, F. Allain, J.F. Dozol, H. Virelizier, J.C. Tabet, C. Moulin, and C. Lamouroux. Rapid Commun. Mass Spectrom. 17, 1247 (2003).
20. V. Lamarre, J.F. Dozol, F. Allain, H. Virelizier, C. Moulin, C.K. Jankowski, and J.C. Tabet. ACS Symp. Vol. 757. Washington, D.C. 2000. Chap. 5. p. 55.
21. C. Lamouroux, N. Aychet, A. Lelièvre, C.K. Jankowski, and C. Moulin. Rapid Commun. Mass Spectrom. 18, 1493 (2004).
22. A. Paquet. Can. J. Chem. 60, 976 (1982).
23. J. Boger, R.J. Corcoran, and J.M. Lehn. Helv. Chim. Acta, 61, 2190 (1978).
24. J.B. Harper, C.J. Easton, and S.F. Lincoln. Tetrahedron Lett. 44, 5815 (2003).
25. J.H. Coates, C.J. Easton, S.J. van Eyk, S.F. Lincoln, B.L. May, C.B. Whalland, and M.L. Williams. J. Chem. Soc. Perkin Trans, 1, 2619 (1990).
26. H. Ikeda, Y. Horimoto, M. Nakata, and A. Ueno. Tetrahedron Lett. 41, 6483 (2000).
27. H. Yamamura, S. Yamada, K. Kohno, N. Okuda, S. Araki, K. Kobayashi, R. Katakai, K. Kano, and M. Kawai. J. Chem. Soc. Perkin Trans, 1, 2943 (1999).
28. T. Lecourt, J.M. Mallet, and P. Sinaÿ. Tetrahedron Lett. 43, 5533 (2002).
29. A. Sartori, A. Casnati, L. Mandolini, F. Sansone, D.N. Reinhoudt, and R. Ungaro. Tetrahedron, 59, 5539 (2003).
30. J. Bügler, N.A.J.M. Sommerdijk, A.J.W.G. Visser, A. van Hoek, R.J.M. Nolte, J.F.J. Engbersen, and D.N. Reinhoudt. J. Am. Chem. Soc. 121, 28 (1999).
31. HyperChem 6.03 Mm+ [computer program]. HyperCube Inc., Gainsville, Fl. 2000.