Potential of amino acid-derived α-amino nitriles for generating molecular diversity

Mini-Reviews in Organic Chemistry

Volumn 5, Issue 3, 2008, Pages 209-221

  González Vera, Juan A ^a   García López, M Teresa ^a   Herranz, Rosario ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

Diversity oriented synthesis; Molecular diversity; Peptidomimetics; Privileged scaffolds; Pseudopeptides; amino nitriles

Indexed keywords

CYANIDES; SCAFFOLDS;

AMINO NITRILES; AMINO-ACIDS; BIOACTIVE PEPTIDES; DIVERSITY-ORIENTED SYNTHESIS; MOLECULAR DIVERSITY; PEPTIDOMIMETICS; PRIVILEGED SCAFFOLD; PSEUDO-PEPTIDE; THREE-COMPONENT; Α-AMINO NITRILE;

AMINO ACIDS;

EID: 50049132629     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157019308785161693     Document Type: Review

References (82)

1. (a) Schreiber, S.L. Science, 2000, 287, 1964.
2. (b) Burke, M.D.; Berger, E.M.; Schreiber, S.L. Science, 2003, 302, 613.
3. (c) Spring, D.R. Org. Biomol. Chem., 2003, 1, 3867.
4. (d) Burke, M.D.; Schreiber, S.L. Angew. Chem. Int. Ed., 2004, 43, 46.
5. Strecker, A. Liebigs. Ann. Chem., 1850, 75, 27.
6. (a) Williams, R.M. In Synthesis of6ptically Active α-Amino Acids, Pergamon Press: Oxford; 1989; pp. 208.
7. (b) Duthaler, O.R. Tetrahedron, 1994, 50, 1539.
8. (c) Enders, D.; Shilvock, J.P. Chem. Soc. Rev., 2000, 29, 359.
9. (d) Ager, D.J.; Fotheringham I. G. Curr. Opin. Drug Discov., 2001, 4, 800.
10. (a) Yet, L. Angew. Chem. Int. Ed., 2001, 40, 875.
11. (b) Gröger, H. Chem. Rev., 2003, 103, 2795.
12. (c) Spino, C. Angew. Chem. Int. Ed., 2004, 43, 1764.
13. Arai, T.; Takahashi, K.; Kubo, A. J. Antibiot., 1977, 30, 1015.
14. Cuevas, C.; Pérez, M.; Martín, M. J.; Chicharro, J. L.; Fernández-Rivas, C.; Flores, M.; Francesch, A.; Gallego, P.; Zarzuelo, M.; de La Calle, F.; García, J.; Polanco, C.; Rodríguez, I.; Manzanares, I. Org. Lett., 2000, 2, 2545.
15. Carter, N.J.; Keam, S.J. Drugs, 2007, 67, 2257.
16. Herranz, R.; Suárez-Gea, M.L.; Vinuesa, S.; García-López, M.T.; Martínez, A. Tetrahedron Lett., 1991, 32, 7579.
17. Herranz, R.; Suárez-Gea, M.L.; Vinuesa, S.; García-López, M.T. J. Org. Chem., 1993, 58, 5186.
18. (a) Patchett, A.A.; Nargund, R.P. In Annual Reports in Medicinal Chemistry, Doherty, A.M. Ed.; Academic Press: San Diego, 2000; Vol. 35, pp. 289.
19. (b) Klabunde, T.; Hessler, G. Chembiochem, 2002, 3, 928.
20. (c) Horton, D.A.; Bourne, G.T.; Smythe, M.L. Chem. Rev., 2003, 103, 893.
21. Spatola, A.F. In Chemistry and Biology of Amino Acids, Peptides and Proteins; Weinstein, B. Ed.; Marcel Dekker: New York, 1983; Vol. 7, pp. 267.
22. (a) Sasaki, Y.; Murphy, W.A.; Herman, M.L.; Lance, V.A.; Coy, D.H. J. Med Chem., 1987, 30, 1162.
23. (b) Rodriguez, M.; Lignon, M.F.; Galas, M.C.; Fulcrand, P.; Mendre, C.; Aumelas, A.; Laur, J.; Martinez, J. J. Med. Chem., 1987, 30, 1366.
24. (a) Martinez, J.; Bali, J.P.; Rodriguez, M.; Castro, B.; Magous, R.; Laur, J.; Lignon, M.F. J. Med. Chem., 1985, 28, 1874.
25. (b) Hocart, S.J.; Nekola, M.V.; Coy, D.H. J. Med. Chem., 1988, 31, 1820.
26. (c) Jensen, R.T.; Coy, D.H. Trends Pharmacol. Sci., 1991, 12, 13.
27. Greenlee, W.J. Med. Res. Rev., 1990, 10, 173.
28. González-Muñiz, R.; García-López, M.T.; Gómez-Monterrey, I.; Herranz, R.; Jimeno,,M.L.; Suárez-Gea, M.L.; Johansen, N.L.; Madsen, K.; Thøgersen, H.; Suzdak, P. J. Med. Chem., 1995, 38, 1015.
29. Herrero, S.; Suárez-Gea, M.L.; González-Muñiz, R.; García-López, M.T.; Herranz, R.; Ballaz, S.; Barber, A.; Fortuño, A.; Del Río, J. Bioorg. Med. Chem. Lett., 1997, 7, 855.
30. Bartolomé-Nebreda, J.M.; Gómez-Monterrey, I.; García-López, M.T.; González-Muñiz, R.; Martín-Martínez, M.; Ballaz, S.; Cenarruzabeitia, E.; LaTorre, M.; Del Río, J.; Herranz, R. J. Med. Chem., 1999, 42, 4659.
31. Alonso de Diego, S.A. Ph.D. Thesis, Autónoma University of Madrid, Spain, October 2007.
32. Suárez-Gea, M.L.; García-López, M.T.; Pérez, C.; Herranz, R. Bioorg. Med. Chem. Lett., 1994, 4, 1491.
33. Umezawa, H. In Small Molecular Immunomodifiers of Microbial Origin. Fundamental and Clinical Studies of Bestatin; Umezawa, H. Ed.; Pergamon Press: Oxford, 1981; pp. 1-16.
34. (a) Kunz, H.; Sager, W. Angew. Chem. Int. Ed. Engl., 1987, 26, 557.
35. (b) Kunz, H.; Sager, W.; Pfrengl, W.; Schansenbach, D. Tetrahedron Lett., 1988, 29, 4397.
36. Tanake, K.; Mori, A.; Inoue, S. J. Org. Chem., 1990, 55, 181.
37. (a) Cortes, S.; Kohn, H. J. Org. Chem., 1983, 48, 2246.
38. (b) Davidsen, S.K.; Chu-Moyer, M.Y. J. Org. Chem., 1989, 54, 5558.
39. Herranz, R.; Suárez-Gea, M.L.; García-López, M.T.; González-Muñiz, R.; Johansen, N.L.; Madsen, K.; Thogersen, H.; Suzdak, P. Tetrahedron Lett., 1993, 34, 8357.
40. González-Vera, J. A.; García-López, M. T.; Herranz, R. J. Org. Chem., 2005, 70, 3660.
41. Ducatel, H.; Van Nhien, A.N.; Postel, D. Tetrahedron Asymmetry, 2008, 19, 67.
42. Myers, G. A.; Kung, D. W. Org. Lett., 2000, 2, 3019.
43. Mohan, R.; Chou, Y.L; Bihovsky, R.; Lumma, W.C.; Erhardt, P.W.; Shaw, K.J. J. Med. Chem., 1991, 34, 2402.
44. Herranz, R.; Conde, S.; Fernández-Resa, P.; Arribas, E. J. Chem. Soc. Perkin Trans. 1, 1988, 649.
45. Suárez-Gea, M.L.; García-López, M.T.; Herranz, R. J. Org. Chem., 1994, 59, 3600.
46. Tam, J.P. Proc. Natl. Acad. Sci. USA, 1988, 85, 5409.
47. (a) Mutter, M.; Vuilleumier, S. Angew. Chem. Int. Ed. Engl., 1989, 28, 535.
48. (b) Grell, D.; Richardson, J.S.; Mutter, M. J. Pept. Sci., 2001, 7, 146.
49. (a) Tam, J.P.; Spetzler, J.C. Biomed. Pept. Proteins Nucleic Acids, 1995, 1, 123.
50. (b) Veprek, P.; Jezek, J. J. Pept. Sci., 1999, 5, 203.
51. Fairlie, D.P.; Sbbenantem, G.; March, D.R. Curr. Med. Chem., 1995, 2, 654.
52. (a) Blackwell, H.E.; Grubbs, R.H. Angew. Chem. Int. Ed. Engl., 1998, 37, 3281.
53. (b) Reichwein, J.F.; Wels, B.; Kruijtzer, J.A.W.; Versluis, C.; Liskamp, R.M.J. Angew. Chem. Int. Ed. Engl., 1999, 38, 3684.
54. (c) Müller, B.; Besser, D.; Kleinwächter, P.; Arad, O.; Reissmarin, S. J. Pept. Res., 1999, 54, 383.
55. Suárez-Gea, M.L.; García-López, M.T.; González-Muñiz, R.; Herrero, S.; Herranz, R. Tetrahedron Lett., 1996, 37, 2083.
56. Herrero, S.; Suárez-Gea, M.L.; García-López, M.T.; Herranz, R. Tetrahedron Lett., 2002, 43, 1421.
57. (a) Rylander, P. Catalytic Hydrogenation in Organic Synthesis, Academic Press: London, 1979.
58. (b) Rylander, P. Hydrogenation Methods, Academic Press: London, 1985.
59. (c) Dallons, J.L.; Van Gysel, A.; Jannes, G. In Catalysis of Organic Reactions; Pascoe, W.E. Ed.; Marcel Dekker: New York, 1992; pp. 93.
60. Evans, B.E.; Rittle, K.E.; Bock, M.G.; DiPardo, R.M.; Freidinger, R.M.; Whitter, W.L.; Lundell, G.F.; Veber, D.F.; Anderson, P.S.; Chang, R.S.L.; Lotti, V.J.; Cerino, D.J.; Chen, T.B.; Kling, P.J.; Kunkel, K.A.; Springer, J.P.; Hirshfield, J. J. Med. Chem., 1988, 31, 2235.
61. (a) Mason, J.S.; Morize, I.; Menard, P.R.; Cheney, D.L.; Hulme, C.; Labaudiniere, R.F. J. Med. Chem., 1999, 42, 3251.
62. (b) Patchett, A.A.; Nargund, R.P. Ann. Rep. Med. Chem., 2000, 35, 289.
63. (a) Freidinger, R.M. Curr. Opin. Chem. Biol., 1999, 3, 395.
64. (b) Ripka, A.S.; Rich, D.H. Curr. Opin. Chem. Biol., 1999, 3, 441.
65. Herrero, S.; García-López, M. T.; Latorre, M.; Cenarruzabeitia, E.; Del Río, J.; Herranz, R.J. Org. Chem., 2002, 67, 3866.
66. Herrero, S.; Salgado, A.; García-López, M. T.; Herranz, R. Tetrahedron Lett., 2002, 43, 4899.
67. González-Vera, J.A.; Garcia-López, M.T.; Herranz, R. Eur. J. Org. Chem., 2007, 70, 548.
68. González-Vera, J.A.; Ventosa-Andrés, P.; Casey, J.; García-López, M.T.; Herrauz, R. Tetrahedron, 2007, 63, 2675.
69. González-Vera, J.A.; García-López, M.T.; Herranz, R. Org. Lett., 2004, 6, 2641.
70. (a) Hino, T.; Taniguchi, M. J. Am. Chem. Soc., 1978, 100, 5564.
71. (b) Taniguchi, M.; Hino, T. Tetrahedron, 1981, 37, 1487.
72. González-Vera, J.A.; García-López, M.T.; Herranz, R. J. Org. Chem., 2005, 70, 8971.
73. (a) Crich, D.; Huang, X. J. Org. Chem., 1999, 64, 7218, and references therein.
74. (b) Depew, K. M.; Marsden, S. P.; Zatorska, D.; Zatorski, A.; Bornmann, W. G.; Danishefsky, S. J. J. Am. Chem. Soc., 1999, 121, 11953, and references therein.
75. (c) Caballero, E.; Avendaño, C.; Menéndez, J. C. J. Org. Chem., 2003, 68, 6944, and references therein.
76. (d) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett., 2000, 2, 675.
77. González-Vera, J.A.; García-López, M.T.; Herranz, R. J. Org. Chem., 2007, 72, 5395.
78. González-Vera, J.A.; García-López, M.T.; Herranz, R. Tetrahedron, 2007, 63, 9229.
79. Kawahara, M.; Nishida, A.; Nakagawa M. Org. Lett., 2000, 2, 675.
80. Corey, E.J.; Kim, C.U. J. Am. Chem. Soc., 1972, 94, 7586.
81. Herrero, S.; García-López, M.T.; Herranz, R. J. Org. Chem., 2003, 68, 4582.
82. Herrero, S.; García-López, M.T.; Cenarruzabeitia, E.; Del Río, J.; Herranz, R. Tetrahedron, 2003, 59, 4491.