Solid-phase synthesis of rigid acylpolyamines using temporary N-4,4′-dimethoxytrityl protection in the presence of trityl linkers

Journal of Organic Chemistry

Volumn 69, Issue 18, 2004, Pages 6149-6152

  Olsen, Christian A ^a   Witt, Matthias ^b   Jaroszewski, Jerzy W ^a   Franzyk, Henrik ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b BRUKER DALTONIK GMBH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE REDUCTION; LIPOPHILICITY;

POLYAMIDES; REDUCTION; RIGIDITY; SYNTHESIS (CHEMICAL);

AMINES;

ACYLPOLYAMINE; BORANE DERIVATIVE; CYCLOHEXYLAMINE; N 4,4' DIMETHOXYTRITYL DERIVATIVE; PHILANTHOTOXIN; POLYAMINE; TRITYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; LIPOPHILICITY; METHODOLOGY; PROTEIN DEGRADATION; REACTION ANALYSIS; REDUCTION; SOLID STATE; SYNTHESIS;

BORANES; CATALYSIS; MOLECULAR STRUCTURE; POLYAMINES; STRUCTURE-ACTIVITY RELATIONSHIP; TRITYL COMPOUNDS; WASP VENOMS;

EID: 4344584772     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049278q     Document Type: Article

References (41)

1. Cohen, S. S. A Guide to Polyamines; Oxford University Press: New York, 1998.
2. Scott, R. H.; Sutton, K. G.; Dolphin, A. C. Trends Neurosci. 1993, 16, 153-160.
3. Williams, K. Biochem. J. 1997, 325, 289-297.
4. Igarashi, K.; Kashiwagi, K. Biochem. Biophys. Res. Commun. 2000, 271, 559-564.
5. Mueller, A. L.; Roeloffs, R.; Jackson, H. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1995; Vol. 46, p 63-94.
6. Strømgaard, K.; Andersen, K.; Krogsgaard-Larsen, P.; Jaroszewski, J. W. Mini Rev. Med. Chem. 2001, 1, 317-338.
7. Strømgaard, K.; Mellor, I. R. Med. Res. Rev. 2004, 24, 589-620.
8. Eldefrawi, A. T.; Eldefrawi, M. E.; Konno, K.; Mansour, N. A.; Nakanishi, K.; Eugene, O.; Usherwood, P. N. R. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4910-4913.
9. Piek, T.; Fokkens, R. H.; Karst, H.; Kruk, C.; Lind, A.; van Marle, J.; Tong, Y. C. In Neurotox 8: Molecular Basis of Drug and Pesticide Action; Lunt, G. G., Ed.; Elsevier: Amsterdam, 1988; pp 61-76.
10. Green, A. C.; Nakanishi, K.; Usherwood, P. N. R. Brain Res. 1996, 717, 135-146.
11. Blagbrough, I. S.; Carrington, S.; Geall, A. J. Pharm. Sci. 1997, 3, 223-233.
12. Casero, R. A.; Woster, P. M. J. Med. Chem. 2001, 44, 1-26.
13. Karigiannis, G.; Papaioannou, D. Eur. J. Org. Chem. 2000, 1841-1863.
14. Kuksa, V.; Buchan, R.; Lin, P. K. T. Synthesis 2000, 1189-1207.
15. Manov, N.; Bienz, S. Tetrahedron 2001, 57, 7893-7898.
16. Manov, N.; Tzouros, M.; Chesnov, S.; Bigler, L.; Bienz, S. Helv. Chim. Acta 2002, 85, 2827-2846.
17. Kan, T.; Kobayashi, H.; Fukuyama, T. Synlett 2002, 8, 1338-1340.
18. Olsen, C. A.; Witt, M.; Jaroszewski, J. W.; Franzyk, H. Org. Lett. 2004, 6, 1935-1938.
19. Hone, N. D.; Payne, L. J. Tetrahedron Lett. 2000, 41, 6149-6152.
20. Strømgaard, K.; Andersen, K.; Ruhland, T.; Krogsgaard-Larsen, P.; Jaroszewski, J. W. Synthesis 2001, 877-884.
21. Olsen, C. A.; Witt, M.; Jaroszewski, J. W.; Franzyk, H. Synlett 2004, 473-476.
22. Chhabra, S. R.; Khan, A. N.; Bycroft, B. W. Tetrahedron Lett. 2000, 41, 1095-1098.
23. Jönsson, D. Tetrahedron Lett. 2002, 43, 4793-4796.
24. Wang, F.; Manku, S.; Hall, D. G. Org. Lett. 2000, 2, 1581-1583.
25. Yoneda, Y.; Mimura, T.; Kawagoe, K.; Yasukouchi, T.; Tatematu, T.; Ito, M.; Saito, M.; Sugimura, M.; Kito, F.; Kawajiri, S. Bioorg. Med. Chem. 2002, 10, 1347-1359.
26. Fixon-Owoo, S.; Levasseur, F.; Williams, K.; Sabado, T. N.; Lowe, M.; Klose, M.; Mercier, A. J.; Fields, P.; Atkinson, J. Phytochemistry 2003, 63, 315-334.
27. Olsen, C. A.; Witt, M.; Jaroszewski, J. W.; Franzyk, H. Org. Lett. 2003, 5, 4183-4185.
28. Nash, I. A.; Bycroft, B. W.; Chan, W. C. J. Chem. Soc., Chem. Commun 1993, 37, 2625-2628.
29. Matysiak, S.; Bøldicke, T.; Tegge, W.; Frank, R. Tetrahedron Lett. 1998, 39, 1733-1734.
30. Consult the Supporting Information for details.
31. Combs, A. P.; Kapoor, T. M.; Feng, S.; Chen, J. K., Daudé-Snow, L. F.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 287-288.
32. Barlos, P. Liebigs Ann. Chem. 1988, 1079-1081.
33. Carpino, L. A.; Tsao, J.-H. J. Chem. Soc., Chem. Commun. 1978, 358-359.
34. Koh, J. S.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494-4495.
35. Paikoff, S. J.; Wilson, T. E.; Cho, C. Y.; Schultz, P. G. Tetrahedron Lett. 1997, 37, 5653-5656.
36. Ostresh, J. M.; Schoner, C. G.; Hamashin, V. T.; Nefvi, A.; Meyer, J.-P.; Houghten, R. A. J. Org. Chem. 1998, 63, 8622-8623.
37. Hall, D. G.; Laplante, C.; Manku, S.; Nagendran, J. J. Org. Chem. 1999, 64, 698-699.
38. Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F. J. Chem. Soc., Chem. Commun. 1994, 201-203.
39. Poulain, R. F.; Tartar, A. L.; Deprez, B. P. Tetrahedron Lett. 2001, 42, 1495-1498.
40. Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205-208.
41. Jacobson, A. R.; Gintzler, A. R.; Sayre, L. M. J. Med. Chem. 1989, 32, 1708-1717.