Microwave-assisted decarboxylation of bicyclic 2-pyridone scaffolds and identification of Aβ-peptide aggregation inhibitors

Organic and Biomolecular Chemistry

Volumn 3, Issue 15, 2005, Pages 2817-2823

  Åberg, Veronica ^a   Norman, Fredrik ^a   Chorell, Erik ^a   Westermark, Andreas ^a   Olofsson, Anders ^a   Elisabeth Sauer Eriksson, A ^a   Almqvist, Fredrik ^a  

^a UMEÅ UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; CARBOXYLIC ACIDS; DEPOSITION; DISEASES; ESTERS; MICROWAVE HEATING; MOLECULAR STRUCTURE; POLYPEPTIDES; PROTEINS; SCAFFOLDS; TOXIC MATERIALS;

AGGREGATION INHIBITORS; ALZHEIMER; PEPTIDES; PYRIDONES;

AROMATIC COMPOUNDS;

AMYLOID BETA PROTEIN; CARBOXYLIC ACID; PEPTIDE; PYRIDONE DERIVATIVE;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMISTRY; DRUG ANTAGONISM; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; INFRARED SPECTROPHOTOMETRY; MICROWAVE RADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

AMYLOID BETA-PROTEIN; CARBOXYLIC ACIDS; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ATOMIC FORCE; MICROWAVES; PEPTIDES; PYRIDONES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, INFRARED;

EID: 23844443559     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b503294f     Document Type: Article

References (31)

1. W. L. Klein, G. A. Krafft and C. E. Finch, Trends Neurosci., 2001, 24, 219.
2. J. P. Cleary, D. M. Walsh, J. J. Hofmeister, G. M. Shankar, M. A. Kuskowski, D. J. Selkoe and K. H. Ashe, Nat. Neurosci., 2005, 8, 79.
3. D. M. Walsh, I. Klyubin, J. V. Fadeeva, M. J. Rowan and D. J. Selkoe, Biochem. Soc. Trans., 2002, 30, 552.
4. A. Lorenzo and B. A. Yankner, Proc. Natl. Acad. Sci. USA, 1994, 91, 12243.
5. C. J. Pike, A. J. Walencewicz, C. G. Glabe and C. W. Cotman, Brain Res., 1991, 563, 311.
6. A. T. Petkova, R. D. Leapman, Z. H. Guo, W. M. Yau, M. P. Mattson and R. Tycko, Science, 2005, 307, 262.
7. R. Kayed, E. Head, J. L. Thompson, T. M. McIntire, S. C. Milton, C. W. Cotman and C. G. Glabe, Science, 2003, 300, 486.
8. T. Berg, Angew. Chem., Int. Ed., 2003, 42, 2462.
9. P. L. Toogood, J. Med. Chem., 2002, 45, 1543.
10. A. G. Cochran, Chem. Biol., 2000, 7, R85.
11. G. Huber Trottman, R. Jakob-Roetne, S. Kolczewski, R. D. Norcross and T. J. Weltering, in: Use of Bi- and Tricyclic Pyridone Derivatives Against Alzheimer's Disease, WO 98/25930, 1998.
12. P. Kuner, B. Bohrmann, L. O. Tjernberg, J. Naslund, G. Huber, S. Celenk, F. Gruninger-Leitch, J. G. Richards, R. Jakob-Roetne, J. A. Kemp and C. Nordstedt, J. Biol. Chem., 2000, 275, 1673.
13. E. D. Thorsett and L. H. Latimer, Curr. Opin. Chem. Biol., 2000, 4, 377.
14. H. Emtenas, L. Alderin and F. Almqvist, J. Org. Chem., 2001, 66, 6756.
15. H. Emtenas, K. Ahlin, J. S. Pinkner, S. J. Hultgren and F. Almqvist, J. Comb. Chem., 2002, 4, 630.
16. H. Emtenas, C. Taflin and F. Almqvist, Mol. Diversity, 2003, 7, 165.
17. J. Meinwald, J. C. Shelton, G. L. Buchanan and A. Courtin, J. Org. Chem., 1968, 33, 99.
18. K. B. Wiberg, B. R. Lowry and T. H. Colby, J. Am. Chem. Soc., 1961, 83, 3998.
19. P. S. Engel and A. Y. Wu, J. Org. Chem., 1994, 59, 3969.
20. W. H. Starnes, J. Am. Chem. Soc., 1964, 86, 5603.
21. T. M. Bookman, S. M. Hubig and J. K. Kochi, J. Org. Chem., 1997, 62, 2210.
22. D. H. R. Barton, D. Crich and W. B. Motherwell, Tetrahedron, 1985, 41, 3901.
23. K. Okada, K. Okamoto and M. Oda, J. Am. Chem. Soc., 1988, 110, 8736.
24. N. Pemberton, V. Aberg, H. Almstedt, A. Westermark and F. Almqvist, J. Org. Chem., 2004, 69, 7830.
25. C. L. Zara, T. Jin and R. J. Giguere, Synth. Commun., 2000, 30, 2099.
26. G. B. Jones and B. J. Chapman, J. Org. Chem., 1993, 58, 5558.
27. C. X. Kuang, H. Senboku and M. Tokuda, Tetrahedron Lett., 2001, 42, 3893.
28. G. Herstad and T. Benneche, J. Heterocycl. Chem., 2003, 40, 219.
29. J. G. Huddleston, H. D. Willauer, R. P. Swatloski, A. E. Visser and R. D. Rogers, Chem. Commun., 1998, 1765.
30. O. Toussaint, P. Capdevielle and M. Maumy, Tetrahedron, 1984, 40, 3229.
31. B. Hin, P. Majer and T. Tsukamoto, J. Org. Chem., 2002, 67, 7365.