Method for the parallel preparation of the aspartic protease isostere: Hydroxyethylamino amides

Journal of Combinatorial Chemistry

Volumn 6, Issue 5, 2004, Pages 688-691

  Coats, Steven J ^a   Schulz, Mark J ^a   Hlasta, Dennis J ^a  

^a Drug Discovery   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ASPARTIC PROTEINASE; ASPARTIC PROTEINASE INHIBITOR; BASE; BENZOIC ACID DERIVATIVE; DICHLOROMETHANE; DIMETHYL SULFOXIDE; EPICHLOROHYDRIN; EPOXIDE; LEWIS ACID; LITHIUM DERIVATIVE; OXIDE; RESIN; TRIFLUOROACETIC ACID; YTTERBIUM;

ACYLATION; ALKYLATION; ARTICLE; DEPROTECTION REACTION; DRUG SYNTHESIS; METHODOLOGY; PROTON TRANSPORT;

AMIDES; ASPARTIC ENDOPEPTIDASES; COMBINATORIAL CHEMISTRY TECHNIQUES; ENZYME INHIBITORS; MOLECULAR MIMICRY; RESINS, SYNTHETIC;

EID: 4944255224     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc049911l     Document Type: Article

References (44)

1. (a) Structure and Function of the Aspartic Proteinases; Dunn, B. M., Ed.; Plenum Press: New York, 1991.
2. (b) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305-41.
3. (c) Bursavich, M. G.; Rich, D. H. J. Med. Chem. 2002, 45, 541-58.
4. (d) Thompson, L. A.; Tebben, A. J. Annu. Rep. Med. Chem. 2001, 36, 247-56.
5. (a) Kornilova, A. Y.; Wolfe, M. S. Annu. Rep. Med. Chem. 2003, 38, 41-50.
6. (b) Wolfe, M. S. J. Med. Chem. 2001, 44, 2039-60.
7. (c) Roggo, S. Curr. Top. Med. Chem. 2002, 2, 359-70.
8. (d) Ghosh, A. K.; Bilcer, G.; Harwood: C.; Kawahama, R.; Shin, D.; Hussain, K. A.; Hong, L.; Loy, J. A.; Nguyen, C.; Koelsch, G.; Ermolieff, J.; Tang, J. J. Med. Chem. 2001, 44, 2865-68.
9. (a) Rochefort, H.; Liaudet-Coopman, E. APMIS 1999, 107, 86-95.
10. (b) Kick, E. K.; Roe, D. C.; Skillman, A. G.; Liu, G.; Ewing, T. J.; Sun, Y.; Kuntz, I. D.; Ellman, J. A. Chem. Biol. 1997, 4, 297-307.
11. (c) Lee, C. E.; Kick, E. K.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 9735-47.
12. (a) Rosenberg, S. H. Renin Inhibitors. In Progress in Medicinal Chemistry; Ellis, G. P., Luscombe, D. K., Eds.; Elsevier Science: New York, 1995; Vol. 32, pp 37-115.
13. (b) Rahuel, J.; Rasetti, V.; Maibaum, J.; Rueger, H.; Göschke, R.; Cohen, N.-C.; Stutz, S.; Cumin, F.; Fuhrer, W.; Wood, J. M.; Grutter, M. G. Chem. Biol. 2000, 7, 493-504.
14. (c) Güller, R.; Binggeli, A.; Breu, V.; Bur, D.; Fischli, W.; Hirth, G.; Jenny, C.; Kansy, M.; Montavon, F.; Müller, M.; Oefner, C.; Stadler, H.; Vieira, E.; Wilhelm, M.; Wostl, W.; Märki, H. P. Bioorg. Med. Chem. Lett. 1999, 9, 1403-8.
15. (a) Haque, T. S.; Skillman, A. G.; Lee, C. E.; Habashita, H.; Gluzman, I. Y.; Ewing, T. J. A.; Goldberg, D. E.; Kuntz, I. D.; Ellman, J. A. J. Med. Chem. 1999, 42, 1428-40.
16. (b) Boss, C.; Richard-Bildstein, S.; Weller, T.; Fischli, W.; Meyer, S.; Binkert, C. Curr. Med. Chem. 2003, 10, 883-907.
17. (a) Dorsey, B. D.; McDonough, C.; McDaniel, S. L.; Levin, R. B.; Newton, C. L.; Hoffman, J. M.; Darke, P. L.; Zugay-Murphy, J. A.; Emini, E. A.; Schleif, W. A.; Olsen, D. B.; Stahlhut, M. W.; Rutkowski, C. A.; Kuo, L. C.; Lin, J. H.; Chen, I.-W.; Michelson, S. R.; Holloway, M. K.; Huff, J. R.; Vacca, J. P. J. Med. Chem. 2000, 43, 3386-99.
18. (b) Rocheblave, L.; Bihel, F.; De Michelis, C.; Priem, G.; Courcambeck, J.; Bonnet, B.; Chermann, J.; Kraus, J. J. Med. Chem. 2002, 45, 3321-24.
19. (c) Di Santo, R.; Costi, R.; Artico, M.; Massa, S.; Ragno, R.; Marshall, G. R.; La Colla, P. Bioorg. Med. Chem. 2002, 10, 2511-26.
20. Lebon, F.; Ledecq, M. Curr. Med. Chem. 2000, 7, 455-77.
21. For other solid-phase or parallel approaches to hydroxyethylamines, see: (a) Kick, E. K.; Ellman, J. A.; Kuntz, I. D.; Lee, C. E.; Liu, G.; Roe, D. C.; Skillman, A. G. U.S. Patent 6,150,416, 1998. (b) Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427-30. (c) Baker, C. T.; Salituro, F. G.; Court, J. J.; Deininger, D. D.; Kim, E. E.; Li, B.; Novak, P. M.; Rao, B. G.; Pazhanisamy, S.; Schairer, W. C.; Tung, R. D. Bioorg. Med. Chem. Lett. 1998, 8, 3631-36. (d) Chino, M.; Wakao, M.; Ellman, J. A. Tetrahedron 2002, 58, 6305-10. (e) Tamamura, H.; Kato, T.; Otaka, A.; Fujii, N. Org. Biomol. Chem. 2003, 1, 2468-73.
22. For other solid-phase or parallel approaches to hydroxyethylamines, see: (a) Kick, E. K.; Ellman, J. A.; Kuntz, I. D.; Lee, C. E.; Liu, G.; Roe, D. C.; Skillman, A. G. U.S. Patent 6,150,416, 1998. (b) Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427-30. (c) Baker, C. T.; Salituro, F. G.; Court, J. J.; Deininger, D. D.; Kim, E. E.; Li, B.; Novak, P. M.; Rao, B. G.; Pazhanisamy, S.; Schairer, W. C.; Tung, R. D. Bioorg. Med. Chem. Lett. 1998, 8, 3631-36. (d) Chino, M.; Wakao, M.; Ellman, J. A. Tetrahedron 2002, 58, 6305-10. (e) Tamamura, H.; Kato, T.; Otaka, A.; Fujii, N. Org. Biomol. Chem. 2003, 1, 2468-73.
23. For other solid-phase or parallel approaches to hydroxyethylamines, see: (a) Kick, E. K.; Ellman, J. A.; Kuntz, I. D.; Lee, C. E.; Liu, G.; Roe, D. C.; Skillman, A. G. U.S. Patent 6,150,416, 1998. (b) Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427-30. (c) Baker, C. T.; Salituro, F. G.; Court, J. J.; Deininger, D. D.; Kim, E. E.; Li, B.; Novak, P. M.; Rao, B. G.; Pazhanisamy, S.; Schairer, W. C.; Tung, R. D. Bioorg. Med. Chem. Lett. 1998, 8, 3631-36. (d) Chino, M.; Wakao, M.; Ellman, J. A. Tetrahedron 2002, 58, 6305-10. (e) Tamamura, H.; Kato, T.; Otaka, A.; Fujii, N. Org. Biomol. Chem. 2003, 1, 2468-73.
24. For other solid-phase or parallel approaches to hydroxyethylamines, see: (a) Kick, E. K.; Ellman, J. A.; Kuntz, I. D.; Lee, C. E.; Liu, G.; Roe, D. C.; Skillman, A. G. U.S. Patent 6,150,416, 1998. (b) Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427-30. (c) Baker, C. T.; Salituro, F. G.; Court, J. J.; Deininger, D. D.; Kim, E. E.; Li, B.; Novak, P. M.; Rao, B. G.; Pazhanisamy, S.; Schairer, W. C.; Tung, R. D. Bioorg. Med. Chem. Lett. 1998, 8, 3631-36. (d) Chino, M.; Wakao, M.; Ellman, J. A. Tetrahedron 2002, 58, 6305-10. (e) Tamamura, H.; Kato, T.; Otaka, A.; Fujii, N. Org. Biomol. Chem. 2003, 1, 2468-73.
25. For other solid-phase or parallel approaches to hydroxyethylamines, see: (a) Kick, E. K.; Ellman, J. A.; Kuntz, I. D.; Lee, C. E.; Liu, G.; Roe, D. C.; Skillman, A. G. U.S. Patent 6,150,416, 1998. (b) Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427-30. (c) Baker, C. T.; Salituro, F. G.; Court, J. J.; Deininger, D. D.; Kim, E. E.; Li, B.; Novak, P. M.; Rao, B. G.; Pazhanisamy, S.; Schairer, W. C.; Tung, R. D. Bioorg. Med. Chem. Lett. 1998, 8, 3631-36. (d) Chino, M.; Wakao, M.; Ellman, J. A. Tetrahedron 2002, 58, 6305-10. (e) Tamamura, H.; Kato, T.; Otaka, A.; Fujii, N. Org. Biomol. Chem. 2003, 1, 2468-73.
26. Dörner, B.; Husar, G. M.; Ostresh, J. M.; Houghten, R. A. Bioorg. Med. Chem. 1996, 4, 709-15.
27. Sennyey, G.; Barcelo, G.; Senet, J.-P. Tetrahedron Lett. 1987, 28, 5809-10.
28. Preformed on a Gilson purification system; typical recoveries are 85%
29. (a) Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1998, 37, 1907-9.
30. (b) Le Hetet, C.; David, M.; Carreaux, F.; Carboni, B.; Sauleau, A. Tetrahedron Lett. 1997, 38, 5153-6.
31. (c) Rotella, D. P. J. Am. Chem. Soc. 1996, 118, 12246-7.
32. (a) Rao, Y. V. S.; De Vos, D. E.; Jacobs, P. A. Angew. Chem., Int. Ed., Engl. 1997, 36, 2661-3.
33. (b) Wendeborn, S.; De Mesmaeker, A.; Brill, W. K.-D. Synlett 1998, 865-8.
34. (c) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-18.
35. (d) Ciobanu, L. C.; Maltais, R.; Poirier, D. Org. Lett. 2000, 2, 445-8.
36. (a) Tan, D. S.; Foley, M. A.; Stockwell, B. R.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 9073-87.
37. (b) Stones, D.; Miller, D. J.; Beaton, M. W.; Rutherford, T. J.; Gani, D. Tetrahedron Lett. 1998, 39, 4875-8.
38. The relative Lewis acid cleavage stability was calculated as follows: From the total absorption chromatogram, the sum of the area of epoxide 7 and hydroxyethylamino amide 10 was divided by the sum of the area of compounds 7, 8, and 10, then corrected for the initial ratio of 7 to 8 (Table 1 footnote c).
39. (a) Randolph, J. T.; Danishefsky, S. J. Angew Chem., Int. Ed., Engl. 1994, 33, 1470-3.
40. (b) Volkmer-Engert, R.; Hoffmann, B.; Schneider-Mergener, J. Tetrahedron Lett. 1997, 38, 1029-32.
41. (a) Hori, M.; Janda, K. D. J. Org. Chem. 1998, 63, 889-94.
42. (b) Rossé, G.; Ouertani, F.; Schröder, H. J. Comb. Chem. 1999, 1, 397-401.
43. (c) Buchstaller, H.-P. Tetrahedron 1998, 54, 3465-70.
44. In the selection of conditions for the identification of an optimal Lewis Acid, we chose a reaction time, which left some starting epoxide 7. This allowed us to obtain a meaningful percent conversion for each set of conditions studied.