Differentially-protected steroidal triamines; scaffolds with potential for medicinal, supramolecular, and combinatorial chemistry

Organic and Biomolecular Chemistry

Volumn 2, Issue 22, 2004, Pages 3320-3328

  Amo, Vicente Del ^a   Siracusa, Laura ^a,b   Markidis, Theodoros ^a   Baragaña, Beatriz ^b   Bhattarai, Khadga M ^a   Galobardes, Marta ^a   Naredo, Gregorio ^a   Pérez Payán, M Nieves ^b   Davis, Anthony P ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHROMATOGRAPHY; FUNCTIONS; PROTEINS; SENSITIVITY ANALYSIS; SYNTHESIS (CHEMICAL);

COMBINATORIAL CHEMISTRY; STERIC HINDRANCE; SYNTHETIC RECEPTORS; TEMPLATES;

SUPRAMOLECULAR CHEMISTRY;

AMINO ACID; AZIDE; CHOLIC ACID; POLYAMINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; ORGANIC CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; AZIDES; CHEMISTRY, ORGANIC; CHOLIC ACID; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; POLYAMINES; STEREOISOMERISM;

EID: 10244256427     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b412298d     Document Type: Article

References (38)

1. (a) S. A. W. Gruner, E. Locardi, E. Lohof and H. Kessler, Chem. Rev., 2002, 102, 491;
2. (b) P. H. Rasmussen and J. Rebek, Tetrahedron Lett., 1999, 40, 3511;
3. (c) G. Wess, K. Bock, H. Kleine, M. Kurz, W. Guba, H. Hemmerle, E. Lopez-Calle, K. H. Baringhaus, H. Glombik, A. Enhsen and W. Kramer, Angew. Chem., Int. Ed. Engl., 1996, 35, 2222;
4. (d) H. De Muynck, A. Madder, N. Farcy, P. J. De Clercq, M. N. Pérez-Payán, L. M. Öhberg and A. P. Davis, Angew. Chem., Int. Ed. Engl, 2000, 39, 145;
5. (e) R. Boyce, G. Li, H. P. Nestler, T. Suenaga and W. C. Still, J. Am. Chem. Soc., 1994, 116, 7955;
6. (f) C. Chamorro and R. M. J. Liskamp, J. Comb. Chem., 2003, 5, 794;
7. (g) N. Farcy, H. De Muynck. A. Madder, N. Hosten and P. J. De Clercq, Org. Lett., 2001, 3, 4299.
8. (a) S. Hecht and J. M. J. Fréchet, Angew. Chem., Int. Ed. Engl, 2001, 40, 74;
9. (b) R. Balasubramanian and U. Maitra, J. Org. Chem., 2001, 66, 3035.
10. (a) M. Mutter, P. Dumy, P. Garrouste, C. Lehmann, M. Mathieu, C. Peggion, S. Peluso, A. Razaname and G. Tuchscherer, Angew. Chem., Int. Ed. Engl., 1996, 35, 1482;
11. (b) H. G. Li and L. X. Wang. Org. Biomol. Chem., 2003, 1, 3507.
12. (a) S. D. Burke, Q. Zhao, M. C. Schuster and L. L. Kiessling, J. Am. Chem. Soc., 2000, 122, 4518;
13. T. Ohta, N. Miura, N. Fujitani, F. Nakajima, K. Niikura, R. Sadamoto, C. T. Guo, T. Suzuki, Y. Suzuki, K. Monde and S. I. Nishimura, Angew. Chem., Int. Ed. Engl, 2003, 42, 5186;
14. (c) H. G. Li and L. X. Wang, Org. Biomol. Oiew., 2004, 2, 483.
15. (a) M. W. Peczuh and A. D. Hamilton, Chem. Rev., 2000, 100, 2479;
16. (b) G. Hennrich and E. V. Anslyn, Chem. -Eur. J., 2002, 8, 2219;
17. (c) A. P. Davis and J.-B. Joos, Coord. Chem. Rev., 2003, 240, 143.
18. Aldrich Handbook of Fine Chemicals and Laboratory Equipment, Aldrich Chemical Company, Milwaukee, WI, USA, 2003/4.
19. Y. A. Cheng, T. Suenaga and W. C. Still, J. Am. Chem. Soc., 1996, 118, 1813.
20. A. Kasal, L. Kohout and M. Lebl, Collect. Czech. Chem. Commun., 1995, 60, 2147.
21. C. H. Li, A. Rehman, N. K. Dalley and P. B. Savage, Tetrahedron Lett., 1999, 40, 1861.
22. J. F. Barry, A. P. Davis, M. N. Pérez-Payán, M. R. J. Elsegood, R. F. W. Jackson, C. Gennari, U. Piarulli and M. Gude, Tetrahedron Lett., 1999, 40, 2849.
23. S. Broderick, A. P. Davis and R. P. Williams, Tetrahedron Lett., 1998, 39, 6083.
24. A. P. Davis and M. N. Pérez-Payán, Synlett, 1999, 991.
25. X. T. Zhou, A. Rehman, C. H. Li and P. B. Savage, Org. Lett., 2000, 2, 3015; P. B. Savage, Eur. J. Org. Chem., 2002, 759.
26. X. T. Zhou, A. Rehman, C. H. Li and P. B. Savage, Org. Lett., 2000, 2, 3015; P. B. Savage, Eur. J. Org. Chem., 2002, 759.
27. Y. R. Vandenburg, B. D. Smith, M. N. Pérez-Payán and A. P. Davis, J. Am. Chem. Soc., 2000, 122, 3252.
28. A. J. Ayling, M. N. Pérez-Payán and A. P. Davis, J. Am. Chem. Soc., 2001, 123, 12716.
29. L. F. Fieser and S. Rajagopalan, J. Am. Chem. Soc., 1950, 72, 5530.
30. J. F. Baker and R. T. Blickenstaff, J. Org. Chem., 1975, 40, 1579 and refs. cited therein.
31. R. P. Bonar-Law, A. P. Davis and J. K. M. Sanders, J. Chem. Soc., Perkin Trans. 1, 1990, 2245.
32. (a) T. Fukuyama, C.-K. Jow and M. Cheung, Tetrahedron Lett., 1995, 36, 6373;
33. S. C. Miller and T. S. Scanlan, J. Am. Chem. Soc., 1998, 120, 2690;
34. (c) K. Nihei, M. J. Kato, T. Yamane, M. S. Palma and K. Konno, Synlett, 2001, 1167.
35. S. Y. Kim, N. D. Sung, J. K. Choi and S. S. Kim, Tetrahedron Lett., 1999, 40, 117.
36. V. O. Topuzyan and M. S. Martirosyan, Zh. Org. Khim., 1991, 27, 2418.
37. Based on the method reported in J. F. Baker and R. T. Blickenstaff, J. Org. Chem., 1975, 40, 1579.
38. R. Grand and T. Reichstein, Helv. Chim. Acta, 1945, 28, 344.