Iterative Oxime Bond Chemistry Leads to Protease Inhibitors

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4693-4696

  Renaudet, Olivier ^a   Reymond, Jean Louis ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; OLIGOMER; OXIME; PROTEINASE INHIBITOR;

ARTICLE; CHEMICAL BOND; ENZYME INHIBITION; MOLECULE;

CHYMOTRYPSIN; CRYSTALLOGRAPHY, X-RAY; INHIBITORY CONCENTRATION 50; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OXIMES; PROTEASE INHIBITORS;

EID: 0346780613     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035867r     Document Type: Article

References (51)

1. For selected reviews, see: (a) Schreiber, S. L. Science 2000, 287, 1964. (b) Weber, L. Drug Discov. Today 2002, 7, 143.
2. For selected reviews, see: (a) Schreiber, S. L. Science 2000, 287, 1964. (b) Weber, L. Drug Discov. Today 2002, 7, 143.
3. For selected reviews, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (c) Soth, M. J.; Nowick, J. S. Curr. Opin. Chem. Biol. 1997, 1, 120. (d) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
4. For selected reviews, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (c) Soth, M. J.; Nowick, J. S. Curr. Opin. Chem. Biol. 1997, 1, 120. (d) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
5. For selected reviews, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (c) Soth, M. J.; Nowick, J. S. Curr. Opin. Chem. Biol. 1997, 1, 120. (d) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
6. For selected reviews, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (c) Soth, M. J.; Nowick, J. S. Curr. Opin. Chem. Biol. 1997, 1, 120. (d) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
7. (a) Simon, R. J.; Kania, R. S.; Zuckermann, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D. C.; Tan, R.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Barlett, P. A. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 9367.
8. (b) Zuckermann, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646.
9. For reviews, see: (a) Seebach, D.; Matthews, J. L. J. Chem. Soc., Chem. Commun. 1997, 21, 2015. (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
10. For reviews, see: (a) Seebach, D.; Matthews, J. L. J. Chem. Soc., Chem. Commun. 1997, 21, 2015. (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
11. Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6568.
12. Gennari, C.; Salom, B.; Potenza, D.; Williams, A. Angew. Chem., Int. Ed. 1994, 33, 2067.
13. Ostresh, J. M.; Husar, G. M.; Blondelle, S. E.; Dömer, B.; Weber, P. A.; Houghten, R. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11138.
14. Moree, W. J.; van der Marel, G. A.; Liskamp, R. J. J. Org. Chem. 1995, 60, 5157.
15. (a) Burgess, K.; Lithicum, K. S.; Shin, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 907.
16. (b) Kim, J.-M.; Bi, Y.; Paikoff, S. J.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5305.
17. Cho, C. Y.; Moran, E. J.; Cherry, S. R.; Stephans, J. C.; Fodor, S. P. A.; Adams, C. L.; Sundaram, A.; Jacobs, J. W.; Schultz, P. G. Science 1993, 261, 1303.
18. Moran, E. J.; Wilson, T. E.; Cho, C. Y.; Cherry, S. R.; Schultz, P. G. Biopolymers 1995, 37, 213.
19. (a) Gante, J. Chem. Ber. 1965, 98, 3340.
20. (b) Gante, J. Synthesis 1994, 405.
21. Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 2539.
22. Cheguillaume, A.; Lehardy, F.; Bouget, K.; Baudy-Floc'h, M.; Grel, P. L. J. Org. Chem. 1999, 64, 2924.
23. Shin, I.; Park, K. Org. Lett. 2002, 4, 869.
24. (a) Rose, K. J. Am. Chem. Soc. 1994, 116, 30.
25. (b) Canne, L. E.; Ferré-D'Amaré, A. R.; Burley, S. K.; Kent, S. B. H. J. Am. Chem. Soc. 1995, 117, 2998.
26. Shao, J.; Tam, J. P. J. Am. Chem. Soc. 1995, 117, 3893.
27. (a) Rodriguez, E. C.; Winans, K. A.; King, D. S.; Bertozzi, C. R. J. Am. Chem. Soc. 1997, 119, 9905.
28. (b) Cervigni, S. E.; Dumy, P.; Mutter, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1230.
29. (c) Renaudet, O.; Dumy, P. Org. Lett. 2003, 5, 243.
30. Forget, D.; Boturyn, D.; Defrancq, E.; Lhomme, J.; Dumy, P. Chem. Eur. J. 2001, 7, 3976.
31. (a) Mahal, L. K.; Yarema, K. J.; Bertozzi, C. R. Science 1997, 276, 1125.
32. (b) Yarema, K. J.; Mahal, L. K.; Bruehl, R. E.; Rodriguez, E. C.; Bertozzi, C. R. J. Biol. Chem. 1998, 273, 31168.
33. By contrast, aliphatic aldehydes and ketones gave E/Z mixtures of oximes, with the exception of pivaldehyde, suggesting that the isomeric equilibrium reflects thermodynamics governed by steric factors.
34. For selected references, see: (a) Carpino, L. A. J. Am. Chem. Soc. 1960, 82, 3133. (b) Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. J. Org. Chem. 1973, 38, 1239. (c) Sheradsky, T. J. Heterocycl. Chem. 1967, 4, 413. (d) Castellino, A. J.; Rapoport, H. J. Org. Chem. 1983, 49, 1348.
35. For selected references, see: (a) Carpino, L. A. J. Am. Chem. Soc. 1960, 82, 3133. (b) Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. J. Org. Chem. 1973, 38, 1239. (c) Sheradsky, T. J. Heterocycl. Chem. 1967, 4, 413. (d) Castellino, A. J.; Rapoport, H. J. Org. Chem. 1983, 49, 1348.
36. For selected references, see: (a) Carpino, L. A. J. Am. Chem. Soc. 1960, 82, 3133. (b) Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. J. Org. Chem. 1973, 38, 1239. (c) Sheradsky, T. J. Heterocycl. Chem. 1967, 4, 413. (d) Castellino, A. J.; Rapoport, H. J. Org. Chem. 1983, 49, 1348.
37. For selected references, see: (a) Carpino, L. A. J. Am. Chem. Soc. 1960, 82, 3133. (b) Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. J. Org. Chem. 1973, 38, 1239. (c) Sheradsky, T. J. Heterocycl. Chem. 1967, 4, 413. (d) Castellino, A. J.; Rapoport, H. J. Org. Chem. 1983, 49, 1348.
38. 4. A few drops of acetic acid and 3-hydroxybenzaldehyde (0.227 g, 1.86 mmol) were added to the organic layer, and then the solvent was evaporated under vacuum. Flash chromatography on silica gel (hexane/ethyl acetate 7: 3) gave 8 as a colorless oil (0.325 g, 51%).
39. (a) Endo, Y.; Shudo, K.; Okamoto, T. Synthesis 1980, 461.
40. (b) Tamura, Y.; Minamikawa, J.; Ikeda, M. Synthesis 1977, 1.
41. Methoxyphenols and 2,5-dimethoxy- or 2,5-dimethylphenols did not give coupling products but only starting phenol, probably due to steric hindrance of the hydroxyl group or electronic factors making the animation difficult. Amination of o-hydroxybenzaldehyde oximes resulted in cleavage by intramolecular transoximation leading to benzisoxazole.
42. Renaudet, O.; Dumy, P. Tetrahedron Lett. 2001, 42, 7575.
43. Meyer, E. A.: Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1212.
44. For selected reviews, see: (a) Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1539. (b) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305. (c) Powers, J. C.; Asgian, J. L.; Ekici, O. D.; James, K. E. Chem. Rev. 2002, 102, 4639. (d) Maly, D. J.; Huang, L.; Ellman, J. A. ChemBioChem 2002, 3, 16.
45. For selected reviews, see: (a) Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1539. (b) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305. (c) Powers, J. C.; Asgian, J. L.; Ekici, O. D.; James, K. E. Chem. Rev. 2002, 102, 4639. (d) Maly, D. J.; Huang, L.; Ellman, J. A. ChemBioChem 2002, 3, 16.
46. For selected reviews, see: (a) Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1539. (b) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305. (c) Powers, J. C.; Asgian, J. L.; Ekici, O. D.; James, K. E. Chem. Rev. 2002, 102, 4639. (d) Maly, D. J.; Huang, L.; Ellman, J. A. ChemBioChem 2002, 3, 16.
47. For selected reviews, see: (a) Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1539. (b) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305. (c) Powers, J. C.; Asgian, J. L.; Ekici, O. D.; James, K. E. Chem. Rev. 2002, 102, 4639. (d) Maly, D. J.; Huang, L.; Ellman, J. A. ChemBioChem 2002, 3, 16.
48. (a) Klein, G.; Reymond, J.-L. Angew. Chem., Int. Ed. 2001, 40, 1771.
49. (b) Dean, K.; Klein, G.; Renaudet O.; Reymond, J.-L. Bioorg. Med. Chem. Lett. 2003, 13, 1653.
50. DelMar, E. G.; Largman, C.; Brodrick, J. W.; Geokas, M. C. Anal. Biochem. 1979, 99, 316.
51. McGovern, S. L.; Caselli, E.; Grigorieff, N.; Shoichet, B. K. J. Med. Chem. 2002, 45, 1712.