Benzoxazoles as transthyretin amyloid fibril inhibitors: Synthesis, evaluation, and mechanism of action

Angewandte Chemie - International Edition

Volumn 42, Issue 24, 2003, Pages 2758-2761

  Razavi, Hossein ^a   Palaninathan, Satheesh K ^b   Powers, Evan T ^a   Wiseman, R Luke ^a   Purkey, Hans E ^a   Mohamedmohaideen, Nilofar N ^b   Deechongkit, Songpon ^a   Chiang, Kyle P ^a   Dendle, Maria T A ^a   Sacchettini, James C ^b   Kelly, Jeffery W ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b NONE

Author keywords

Aggregation; Bioorganic chemistry; Drug design; Inhibitors; Structure activity relationships

Indexed keywords

CRYSTAL STRUCTURE; DISSOCIATION; UREA;

AMYLOID FORMATION;

AROMATIC COMPOUNDS;

AMYLOID; BENZOXAZOLE DERIVATIVE; PREALBUMIN; TETRAMER; UREA;

AMYLOIDOSIS; ARTICLE; CRYSTAL STRUCTURE; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS;

AMYLOID; BENZOXAZOLES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; PREALBUMIN;

EID: 10744228786     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351179     Document Type: Article

References (24)

1. J. D. Sipe, Crit. Rev. Clin. Lab. Sci. 1994, 31, 325.
2. J. W. Kelly, Curr. Opin. Struct. Biol. 1996, 6, 11.
3. C. C. Blake, M. J. Geisow, S. J. Oatley, B. Rerat, C. Rerat, J. Mol. Biol. 1978, 121, 339.
4. L. Bartalena, J. Robbins, Clin. Lab. Med. 1993, 13, 583.
5. H. L. Monaco, Biochim. Biophys. Acta 2000, 1482, 65.
6. J. W. Kelly, W. Colon, Z. Lai, H. A. Lashuel, J. McCulloch, S. L. McCutchen, G. J. Miroy, S. A. Peterson, Adv. Protein Chem. 1997, 50, 161.
7. R. E. McCarthy III, E. K. Kasper, Clin. Cardiol. 1998, 21, 547.
8. V. Plante-Bordeneuve, G. Said, Curr. Opin. Neurobiol. 2000, 13, 569.
9. D. R. Jacobson, R. D. Pastore, R. Yaghoubian, I. Kane, G. Gallo, F. S. Buck, J. N. Buxbaum, N. Engl. J. Med. 1997, 336, 466.
10. P. Hammarstrom, F. Schneider, J. W. Kelly, Science 2001, 293, 2459.
11. P. Hammarstrom, R. L. Wiseman, E. T. Powers, J. W Kelly, Science 2003, 299, 713.
12. J. C. Sacchettini, J. W. Kelly, Nat. Rev. Drug Discov. 2002, 1, 267..
13. G. J. Miroy, Z. Lai, H. A. Lashuel, S. A. Peterson, C. Strang, J. W. Kelly, Proc. Natl. Acad. Sci. USA 1996, 93, 15051.
14. S. A. Peterson, T. Klabunde, H. A. Lashuel, H. Purkey, J. C. Sacchettini, J. W. Kelly, Proc. Natl. Acad. Sci. USA 1998, 95, 12956.
15. P. W. Baures, S. A. Peterson, J. W. Kelly, Bioorg. Med. Chem. 1998, 6, 1389.
16. P. W. Baures, V. B. Oza, S. A. Peterson, J. W. Kelly, Bioorg. Med. Chem. 1999, 7, 1339.
17. V. B. Oza, H. M. Petrassi, H. E. Purkey, J. W. Kelly, Bioorg. Med. Chem. Lett. 1999, 9, 1.
18. T. Klabunde, H. M. Petrassi, V. B. Oza, P. Raman, J. W. Kelly, J. C. Sacchettini, Nat. Struct. Biol. 2000, 7, 312.
19. H. M. Petrassi, T. Klabunde, J. Sacchettini, J. W. Kelly, J. Am. Chem. Soc. 2000, 122, 2178.
20. V. B. Oza, C. Smith, P. Raman, E. K. Koepf, H. A. Lashuel, H. M. Petrassi, K. P. Chiang, E. T. Powers, J. Sacchettinni, J. W. Kelly, J. Med. Chem. 2002, 45, 321.
21. M. Terashima, M. Ishii, Synthesis 1982, 484.
22. M. R. DeLuca, S. M. Kerwin, Tetrahedron 1997, 53, 457.
23. H. E. Purkey, M. I. Dorrell, J. W. Kelly, Proc. Natl. Acad. Sci. USA 2001, 98, 5566.
24. M. H. Teng, J. Y. Yin, R. Vidal, J. Ghiso, A. Kumar, R. Rabenou, A. Shah, D. R. Jacobson, C. Tagoe, G. Gallo, J. Buxbaum, Lab. Invest. 2001, 81, 385.