Stereoselective synthesis of E-64 and related cysteine proteases inhibitors from 2,3-epoxyamides

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 5, 2005, Pages 1691-1705

  Sarabia, Francisco ^a   Sánchez Ruiz, Antonio ^a   Chammaa, Samy ^a  

^a UNIVERSITY OF MÁLAGA   (Spain)

Author keywords

CA 074; Cathepsins; Cysteine proteases inhibitors; E 64; Epoxyamides; Stereoselective synthesis; Sulfur ylides

Indexed keywords

ACETAL DERIVATIVE; AMIDE; CYSTEINE PROTEINASE INHIBITOR; EPOXIDE; INDOLE DERIVATIVE; SUCCINIC ACID DERIVATIVE;

ARTICLE; DEGRADATION KINETICS; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION KINETICS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 13444266214     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.12.018     Document Type: Article

References (48)

1. K. Hanada, M. Tamai, M. Yamagishi, S. Ohmura, J. Samada, and I. Tanaka Agric. Biol. Chem. 42 1978 523 528
2. J.P. Meara, and D.H. Rich J. Med. Chem. 39 1996 3357 3366
3. M. Murata, S. Miyashita, C. Yokoo, M. Tamai, K. Hanada, K. Hatayama, T. Towatari, T. Nikawa, and N. Katunuma FEBS Lett. 280 1991 307 310
4. H.H. Otto, and T. Schirmeister Chem. Rev. 97 1997 133 171 and references cited therein
5. S. Hashida, T. Towatari, E. Kominami, and N. Katunuma J. Biochem. 88 1980 1805
6. B. Grinde Biochim. Biophys. Acta 701 1982 328
7. S. Hashida, E. Kominami, and N. Katunuma J. Biochem. 91 1982 1373
8. T. Noda, K. Isogai, N. Katunuma, Y. Tarumoto, and M. Ohzeki J. Biochem. 90 1981 893
9. M. Tamai, K. Matsumoto, S. Omura, I. Koyama, Y. Ozawa, and K. Hanada J. Pharmacobiodyn. 9 1986 672
10. T. Ohshita, T. Nikawa, T. Towatari, and N. Katunuma Eur. J. Biochem. 209 1992 223
11. Y. Maekawa, K. Himeno, H. Ishikawa, H. Hisaeda, T. Sakai, T. Dainichi, T. Asao, R.A. Good, and N. Katunuma J. Immunol. 161 1998 2120
12. N. Katunuma, Y. Matsunaga, A. Matsui, H. Kakegawa, K. Endo, T. Inubushi, T. Saibara, Y. Ohba, and T. Kakiuchi Adv. Enzyme Regul. 38 1998 235
13. Y. Matsunaga, T. Saibara, H. Kido, and N. Katunuma FEBS Lett. 324 1993 325
14. T. Zhang, Y. Maekawa, J. Hanba, T. Dainichi, B.F. Nashed, H. Hisaeda, T. Sakai, T. Asao, K. Himeno, R.A. Good, and N. Katunuma Immunology 100 2000 13
15. S.T. Yee, Y. Okada, K. Ogasawara, S. Omura, A. Takatsuki, T. Kakiuchi, D. Muno, E. Kominami, and T. Mizuochi Microbiol. Immunol. 41 1997 563
16. M. Bogyo, S. Verhelst, V. Bellingard-Dubouchaud, S. Toba, and D. Greenbaum Chem. Biol. 7 2000 27
17. K. Tsuchiya, Y. Kohda, M. Yoshida, L. Zhao, T. Ueno, J. Yamashita, T. Yoshioka, E. Kominami, and T. Yamashima Exp. Neurol. 155 1999 187
18. T. Yamashima, Y. Kohda, K. Tsuchiya, T. Ueno, J. Yamashita, T. Yoshioka, and E. Kominami Eur. J. Neurosci. 10 1998 1723
19. W.R. Roush, A. Alvarez Hernandez, and G. Zepeda Synthesis 1999 1500 1504
20. A. Korn, S. Rudolph-Böhner, and L. Moroder Tetrahedron 50 1994 8381 8392
21. J.L. Asgian, K.E. James, Z.Z. Li, W. Carter, A.J. Barrett, J. Mikolajczyk, G.S. Salvesen, and J.C. Powers J. Med. Chem. 45 2002 4958 4960
22. D. Greenbaum, K.F. Medzihradsky, A. Burlingame, and M. Bogyo Chem. Biol. 7 2000 569 581
23. J.C. Powers, J.L. Asgian, O.D. Ekici, and K.E. James Chem. Rev. 102 2002 4639 4750
24. F.J. López Herrera, F.R. Sarabia García, and M.S. Pino González Recent Res. Devel. Org. Chem. 4 2000 465 490
25. F.J. López Herrera, F. Sarabia García, G.M. Pedraza Cebrián, and M.S. Pino González Tetrahedron Lett. 40 1999 1379 1380
26. F.J. López-Herrera, C. Assiego, and M.S. Pino González Tetrahedron Lett. 44 2003 8353 8356
27. C. Assiego, M.S. Pino González, and F.J. López-Herrera Tetrahedron Lett. 45 2004 2611 2613
28. L. Martín-Ortiz, S. Chammaa, M.S. Pino-González, A. Sánchez-Ruiz, M. García-Castro, C. Assiego, and F. Sarabia Tetrahedron Lett. 45 2004 9069 9072
29. M. Valpuesta Fernández, P. Durante-Lanes, and F.J. López-Herrera Tetrahedron 46 1990 7911 7922
30. M. Valpuesta-Fernández, P. Durante-Lanes, and F.J. López Herrera Tetrahedron 49 1993 9547
31. F.J. López Herrera, A. Heras López, M.S. Pino González, and F. Sarabia García J. Org. Chem. 61 1996 8839 8848
32. F.J. López-Herrera, F. Sarabia García, A. Heras López, J.J. Ortega Alcántara, G.M. Pedraza Cebrián, and M.S. Pino-González Tetrahedron: Asymmetry 7 1996 2065 2071
33. F.J. López Herrera, F. Sarabia García, A. Heras López, and M.S. Pino González J. Org. Chem. 62 1997 6056 6059
34. A. Heras-López, M.S. Pino-González, F. Sarabia- García, and F.J. López-Herrera J. Org. Chem. 63 1998 9630 9634
35. J. Jurczak, S. Pikuly, and T. Bauer Tetrahedron 42 1986 447
36. M.J.V. de Oliveira Baptista, A.G.M. Barrett, D.H.R. Barton, M. Girijavallabhan, R.C. Jennings, J. Kelly, V.J. Papadimitriou, J.V. Turner, and N.A. Usher J. Chem. Soc., Perkin Trans. 1 1977 1477 1500
37. K.C. Nicolaou, Y.-L. Zhong, P.S. Baran, J. Jung, H.-S. Choi, and W.H. Yoon J. Am. Chem. Soc. 124 2002 2202 2211
38. F. Sarabia, L. Martín-Ortiz, and F.J. López-Herrera Org. Lett. 5 2003 3927 3930
39. M. Daumas, Y. Vo-Quang, L. Vo-Quang, and F. Le Goffic Synthesis 1989 64 65
40. B.R. Travis, M. Sivakumar, G.O. Hollist, and B. Borhan Org. Lett. 5 2003 1031 1034
41. M. Carmignani, A.R. Volpe, B. Botta, R. Espinal, S.C. De Bonnevaux, C. De Luca, M. Botta, F. Corelli, A. Tafi, R. Sacco, and G. Delle Monache J. Med. Chem. 44 2001 2950 2958
42. D.L. Boger, M.W. Ledeboer, M. Kume, M. Searcey, and Q. Jin J. Am. Chem. Soc. 121 1999 11375 11383
43. G. Atwell, and W.A. Denny Synthesis 1984 1032 1033
44. J. Jones The Chemical Synthesis of Peptides (The International Series of Monographs on Chemistry, No 23) 1991 Oxford Science Publications Oxford pp 42-75
45. E-64 (1) was purchased from SIGMA-ALDRICH
46. M.P.M. van Aar, L. Thijs, and B. Zwanenburg Tetrahedron 51 1995 9699 9712
47. G. Zweifel, and H. Arzoumanian J. Am. Chem. Soc. 89 1967 291 295
48. M. Tamai, C. Yokoo, M. Murata, K. Oguma, K. Sota, E. Sato, and Y. Kanaoka Chem. Pharm. Bull. 35 1987 1098 1104