Novel Peptide-Heterocycle Hybrids: Synthesis and Preliminary Studies on Calpain Inhibition

Advanced Synthesis and Catalysis

Volumn 344, Issue 8, 2002, Pages 855-867

  Mann, Enrique ^a   Chana, Antonio ^a   Sánchez Sancho, Francisco ^a   Puerta, Carmen ^b   García Merino, Antonio ^b   Herradón, Bernardo ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b HOSPITAL UNIVERSITARIO PUERTA DE HIERRO   (Spain)

Author keywords

Aromatic compounds; Calpain inhibitor; Heterocycles; Peptide heterocyclic hybrids

Indexed keywords

EID: 0012843434     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200209)344:8<855::AID-ADSC855>3.0.CO;2-1     Document Type: Article

References (94)

1. For some recent reviews on different aspects of peptides and related compounds, see: a) B. Gutte (Ed.), Peptides: Synthesis, Structures, and Applications, Academic Press, San Diego, 1995; b) A. Giannis, F. Rübsam, Adv. Drug Res. 1997, 29, 1-77; c) S. H. Gellman, Curr. Op. Chem. Biol. 1998, 2, 717-725; d) M. J. I. Andrews, A. B. Tabor, Tetrahedron 1999, 55, 11711-11743; e) L. Batzer, Topics in Current Chemistry 1999, 202, 39-76; f) O. Seitz, I. Heinemann, A. Mattes, H. Waldmann, Tetrahedron 2001, 57, 2247-2277; g) J. Venkatraman, S. C. Shankaramma, P. Balaram, Chem. Rev. 2001, 101, 3131-3152; h) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219-3232.
2. For some recent reviews on different aspects of peptides and related compounds, see: a) B. Gutte (Ed.), Peptides: Synthesis, Structures, and Applications, Academic Press, San Diego, 1995; b) A. Giannis, F. Rübsam, Adv. Drug Res. 1997, 29, 1-77; c) S. H. Gellman, Curr. Op. Chem. Biol. 1998, 2, 717-725; d) M. J. I. Andrews, A. B. Tabor, Tetrahedron 1999, 55, 11711-11743; e) L. Batzer, Topics in Current Chemistry 1999, 202, 39-76; f) O. Seitz, I. Heinemann, A. Mattes, H. Waldmann, Tetrahedron 2001, 57, 2247-2277; g) J. Venkatraman, S. C. Shankaramma, P. Balaram, Chem. Rev. 2001, 101, 3131-3152; h) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219-3232.
3. For some recent reviews on different aspects of peptides and related compounds, see: a) B. Gutte (Ed.), Peptides: Synthesis, Structures, and Applications, Academic Press, San Diego, 1995; b) A. Giannis, F. Rübsam, Adv. Drug Res. 1997, 29, 1-77; c) S. H. Gellman, Curr. Op. Chem. Biol. 1998, 2, 717-725; d) M. J. I. Andrews, A. B. Tabor, Tetrahedron 1999, 55, 11711-11743; e) L. Batzer, Topics in Current Chemistry 1999, 202, 39-76; f) O. Seitz, I. Heinemann, A. Mattes, H. Waldmann, Tetrahedron 2001, 57, 2247-2277; g) J. Venkatraman, S. C. Shankaramma, P. Balaram, Chem. Rev. 2001, 101, 3131-3152; h) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219-3232.
4. For some recent reviews on different aspects of peptides and related compounds, see: a) B. Gutte (Ed.), Peptides: Synthesis, Structures, and Applications, Academic Press, San Diego, 1995; b) A. Giannis, F. Rübsam, Adv. Drug Res. 1997, 29, 1-77; c) S. H. Gellman, Curr. Op. Chem. Biol. 1998, 2, 717-725; d) M. J. I. Andrews, A. B. Tabor, Tetrahedron 1999, 55, 11711-11743; e) L. Batzer, Topics in Current Chemistry 1999, 202, 39-76; f) O. Seitz, I. Heinemann, A. Mattes, H. Waldmann, Tetrahedron 2001, 57, 2247-2277; g) J. Venkatraman, S. C. Shankaramma, P. Balaram, Chem. Rev. 2001, 101, 3131-3152; h) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219-3232.
5. For some recent reviews on different aspects of peptides and related compounds, see: a) B. Gutte (Ed.), Peptides: Synthesis, Structures, and Applications, Academic Press, San Diego, 1995; b) A. Giannis, F. Rübsam, Adv. Drug Res. 1997, 29, 1-77; c) S. H. Gellman, Curr. Op. Chem. Biol. 1998, 2, 717-725; d) M. J. I. Andrews, A. B. Tabor, Tetrahedron 1999, 55, 11711-11743; e) L. Batzer, Topics in Current Chemistry 1999, 202, 39-76; f) O. Seitz, I. Heinemann, A. Mattes, H. Waldmann, Tetrahedron 2001, 57, 2247-2277; g) J. Venkatraman, S. C. Shankaramma, P. Balaram, Chem. Rev. 2001, 101, 3131-3152; h) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219-3232.
6. For some recent reviews on different aspects of peptides and related compounds, see: a) B. Gutte (Ed.), Peptides: Synthesis, Structures, and Applications, Academic Press, San Diego, 1995; b) A. Giannis, F. Rübsam, Adv. Drug Res. 1997, 29, 1-77; c) S. H. Gellman, Curr. Op. Chem. Biol. 1998, 2, 717-725; d) M. J. I. Andrews, A. B. Tabor, Tetrahedron 1999, 55, 11711-11743; e) L. Batzer, Topics in Current Chemistry 1999, 202, 39-76; f) O. Seitz, I. Heinemann, A. Mattes, H. Waldmann, Tetrahedron 2001, 57, 2247-2277; g) J. Venkatraman, S. C. Shankaramma, P. Balaram, Chem. Rev. 2001, 101, 3131-3152; h) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219-3232.
7. For some recent reviews on different aspects of peptides and related compounds, see: a) B. Gutte (Ed.), Peptides: Synthesis, Structures, and Applications, Academic Press, San Diego, 1995; b) A. Giannis, F. Rübsam, Adv. Drug Res. 1997, 29, 1-77; c) S. H. Gellman, Curr. Op. Chem. Biol. 1998, 2, 717-725; d) M. J. I. Andrews, A. B. Tabor, Tetrahedron 1999, 55, 11711-11743; e) L. Batzer, Topics in Current Chemistry 1999, 202, 39-76; f) O. Seitz, I. Heinemann, A. Mattes, H. Waldmann, Tetrahedron 2001, 57, 2247-2277; g) J. Venkatraman, S. C. Shankaramma, P. Balaram, Chem. Rev. 2001, 101, 3131-3152; h) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219-3232.
8. For some recent reviews on different aspects of peptides and related compounds, see: a) B. Gutte (Ed.), Peptides: Synthesis, Structures, and Applications, Academic Press, San Diego, 1995; b) A. Giannis, F. Rübsam, Adv. Drug Res. 1997, 29, 1-77; c) S. H. Gellman, Curr. Op. Chem. Biol. 1998, 2, 717-725; d) M. J. I. Andrews, A. B. Tabor, Tetrahedron 1999, 55, 11711-11743; e) L. Batzer, Topics in Current Chemistry 1999, 202, 39-76; f) O. Seitz, I. Heinemann, A. Mattes, H. Waldmann, Tetrahedron 2001, 57, 2247-2277; g) J. Venkatraman, S. C. Shankaramma, P. Balaram, Chem. Rev. 2001, 101, 3131-3152; h) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219-3232.
9. Several terms (sometimes poorly defined) have been used to name peptide analogues (peptidomimetic, peptoid, peptide isostere, peptide conjugate, and so on), creating some confusion.
10. a) D. Tourwé, Janssen Chimica Acta 1985, 3, 1-18;
11. b) D. Yang, J. Qu, B. Li, F.-F. Ng, X.-C. Wang, K.-K. Cheung, D.-P. Wang, Y.-D. Wu J. Am. Chem. Soc. 1999, 121, 589-590;
12. c) R. Günther, H.-J. Hofmann, J. Am. Chem. Soc. 2001, 123, 247-255;
13. d) A. Cheguillaume, A. Salaün, S. Sindandhit, M. Potel, P. Gall, M. Baudy-Floc'h, P. Le Grel, J. Org. Chem. 2001, 66, 4923-4929.
14. a) C. Toniolo, Int. J. Peptide Protein Res. 1990, 35, 287-300;
15. b) R. M. Liskamp, Recl. Trav. Chim. Pays-Bas 1994, 113, 1-19;
16. c) S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789-12854;
17. d) S. E. Gibson (née Thomas), N. Guillo, M. J. Tozer, Tetrahedron 1999, 55, 585-615.
18. Either the full peptide chain or only side chains have been linked to the non-peptidic cyclic compound.
19. a) J. P. Schneider, J. W. Kelly, Chem. Rev. 1995, 95, 2169-2187;
20. b) J. S. Nowick, E. M. Smith, M. Pairish, Chem. Soc. Rev. 1996, 401-415;
21. c) K. D. Stigers, M. J. Soth, J. S. Nowick, Curr. Op. Chem. Biol. 1999, 3, 714-723;
22. d) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893-4011.
23. There is a fourth strategy, that is the use of a structurally unrelated compound that imitates the biological activity of a peptide. A historical case is morphine and related opioid compounds; for an overview, see: T. Nogrady, Medicinal Chemistry. A Biochemical Approach, 2nd ed., Oxford University Press, Oxford, 1988, pp. 306-320. It has been proved in some cases that the endogenous peptide and the peptidomimetic bind to different subsites at the receptor; for a discussion, see: A. S. Ripka, D. H. Rich, Curr. Op. Chem. Biol. 1998, 2, 441-452.
24. There is a fourth strategy, that is the use of a structurally unrelated compound that imitates the biological activity of a peptide. A historical case is morphine and related opioid compounds; for an overview, see: T. Nogrady, Medicinal Chemistry. A Biochemical Approach, 2nd ed., Oxford University Press, Oxford, 1988, pp. 306-320. It has been proved in some cases that the endogenous peptide and the peptidomimetic bind to different subsites at the receptor; for a discussion, see: A. S. Ripka, D. H. Rich, Curr. Op. Chem. Biol. 1998, 2, 441-452.
25. a) G. D. Rose, L. M. Gierasch, J. A. Smith, Adv. Protein Chem. 1985, 37, 1-109;
26. b) M. Kahn, Synlett 1993, 821-826;
27. c) For a recent computational comparative study on β-turn mimetics, see: G. Müller, G. Hessler, H. Y. Decornez, Angew. Chem. Int. Ed. 2000, 39, 894-896;
28. d) For a critical analysis of the conformational properties of peptidomimetics, see: P. Gillespie, J. Cicariello, G. L. Olson, Biopolymers 1997, 43, 191-217.
29. For a recent book on the generation of molecular diversity using combinatorial strategies, see: D. Obrecht, J. M. Villalgordo, Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries, Pergamon, Oxford, 1998.
30. a) D. E. Hibbs, M. B. Hursthouse, I. G. Jones, W. Jones, K. M. A. Malik, M. North, J. Org. Chem. 1998, 63, 1496-1504;
31. b) D. Ranganathan, V. Haridas, S. Kurur, R. Nagaraj, E. Bikshapathy, A. C. Kunwar, A. V. S. Sarma, M. Vairamani, J. Org. Chem. 2000, 65, 365-374; and references cited in these papers.
32. R. Hirschmann, P. A. Sprengeler, T. Kawasaki, J. W. Leahy, W. C. Shakespeare, A. B. Smith III, Tetrahedron 1993, 49, 3665-3676; and references cited therein.
33. a) W. P. Nolan, G. S. Ratcliffe, D. C. Rees, Tetrahedron Lett. 1992, 33, 6879-6882;
34. b) T. Moriuchi, A. Nomoto, K, Yoshida, A. Ogawa, T. Hirao, J. Am. Chem. Soc. 2001, 123, 68-75;
35. c) J. S. Nowick, J. M. Cary, J. H. Tsai, J. Am. Chem. Soc. 2001, 123, 5176-5180.
36. a) R. Hirschmann, K. C. Nicolaou, S. Pietranico, E. M. Leahy, J. Salvino, B. Arison, M. A. Cichy, P. G. Spoors, W. C. Shakespeare, P. A. Sprengeler, P. Hamley, A. B. Smith III, T. Reisine, K. Raynor, L. Maechler, C. Donaldson, W. Vale, R. M. Freidiger, M. A. Cascieri, C. D. Strader, J. Am. Chem. Soc. 1993, 115, 12550-12568;
37. b) E. Graf von Roedern, E. Lohof, G. Hessler, M. Hoffmann, H. Kessler, J. Am. Chem. Soc. 1996, 118, 10156-10167;
38. c) K. C. Nicolaou, J. I. Trujillo, K. Chibale, Tetrahedron 1997, 53, 8571-8778;
39. d) Y. Suhara, M. Izumi, M. Ichikawa, M. B. Penno, Y. Ichikawa, Tetrahedron Lett. 1997, 38, 7167-7170;
40. e) H. S. Overkleeft, S. H. L. Verhelst, E. Pieterman, N. J. Meeuwenoord, M. Overhand, L. H. Cohen, G. A. van der Marel, J. H. van Boom, Tetrahedron Lett. 1999, 40, 4103-4106;
41. f) M. D. Smith, G. W. J. Fleet, J. Peptide Science 1999, 5, 425-441;
42. g) T. K. Chakraborty, S. Ghosh, S. Jayaprakash, J. A. R. P. Sharma, V. Ravikanth, P. V. Diwan, R. Nagaraj, A. C. Kunwar, J. Org. Chem. 2000, 65, 6441-6447;
43. h) U. Koert, J. Prakt. Chem. 2000, 342, 325-333;
44. i) F. Schweizer, Angew. Chem. Int. Ed. 2002, 41, 230-253;
45. j) S. A. W. Gruner, E. Locardi, E. Lohof, H. Kessler, Chem. Rev. 2002, 102, 491-514; and references cited in these papers.
46. a) K. H. Lee, G. L. Olson, D. R. Bolin, A. B. Benowitz, P. A. Sprengeler, A. B. Smith III, R. Hirschmann, D. C. Wiley, J. Am. Chem. Soc. 2000, 122, 8370-8375;
47. b) R. Kaul, A. R. Angeles, M. Jäger, E. T. Powers, J. W. Kelly, J. Am. Chem. Soc. 2001, 123, 5206-5212;
48. c) W. Maison, E. Arce, P. Renold, R. J. Kennedy, D. S. Kemp, J. Am. Chem. Soc. 2001, 123, 10245-10254;
49. d) S. T. Phillips, M. Rezac, U. Abel, M. Kossenjans, P. A. Bartlett, J. Am. Chem. Soc. 2002, 124, 58-66; and references cited therein.
50. a) F. Sánchez-Sancho, E. Mann, B. Herradón, Synlett 2000, 509-513;
51. b) F. Sánchez-Sancho, E. Mann, B. Herradón, Adv. Synth. Catal. 2001, 343, 360-368.
52. The parent ring system of compound 3 in IUPAC-nomenclature is pyrido[1,2-b]isoquinoline (Pure Appl. Chem. 1998, 7, 143-216) and in CAS-nomenclature is benzo[b]quinolizidine.
53. N. J. Heaton, P. Bello, B. Herradón, A. del Campo, J. Jiménez-Barbero, J. Am. Chem. Soc. 1998, 120, 9632-9645.
54. Aromatic rings can interact with diverse chemical functionalities through a variety of intermolecular forces (hydrogen bond, hydrophobic interactions, electrostatic interactions, and so on), that influence on their structures, physical and biological properties; for some reviews and leading references, see: a) S. K. Burley, G. A. Petsko, Adv. Protein Chem. 1988, 39, 125-189. b) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534; c) L. F. Newcomb, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 4993-4994; d) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; e) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324; f) J. P. Glusker, Topics in Current Chemistry 1998, 198, 1-109; g) G. W. Gokel, S. L. De Wall, E. S. Meadows, Eur. J. Org. Chem. 2000, 2967-2978; h) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669. i) McKay, S. L.; Haptonstall, B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 1244-1245. j) V. G. S. Box, F. Jean-Mary, J. Mol. Mod. 2001, 7, 334-342.
55. Aromatic rings can interact with diverse chemical functionalities through a variety of intermolecular forces (hydrogen bond, hydrophobic interactions, electrostatic interactions, and so on), that influence on their structures, physical and biological properties; for some reviews and leading references, see: a) S. K. Burley, G. A. Petsko, Adv. Protein Chem. 1988, 39, 125-189. b) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534; c) L. F. Newcomb, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 4993-4994; d) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; e) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324; f) J. P. Glusker, Topics in Current Chemistry 1998, 198, 1-109; g) G. W. Gokel, S. L. De Wall, E. S. Meadows, Eur. J. Org. Chem. 2000, 2967-2978; h) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669. i) McKay, S. L.; Haptonstall, B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 1244-1245. j) V. G. S. Box, F. Jean-Mary, J. Mol. Mod. 2001, 7, 334-342.
56. Aromatic rings can interact with diverse chemical functionalities through a variety of intermolecular forces (hydrogen bond, hydrophobic interactions, electrostatic interactions, and so on), that influence on their structures, physical and biological properties; for some reviews and leading references, see: a) S. K. Burley, G. A. Petsko, Adv. Protein Chem. 1988, 39, 125-189. b) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534; c) L. F. Newcomb, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 4993-4994; d) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; e) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324; f) J. P. Glusker, Topics in Current Chemistry 1998, 198, 1-109; g) G. W. Gokel, S. L. De Wall, E. S. Meadows, Eur. J. Org. Chem. 2000, 2967-2978; h) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669. i) McKay, S. L.; Haptonstall, B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 1244-1245. j) V. G. S. Box, F. Jean-Mary, J. Mol. Mod. 2001, 7, 334-342.
57. Aromatic rings can interact with diverse chemical functionalities through a variety of intermolecular forces (hydrogen bond, hydrophobic interactions, electrostatic interactions, and so on), that influence on their structures, physical and biological properties; for some reviews and leading references, see: a) S. K. Burley, G. A. Petsko, Adv. Protein Chem. 1988, 39, 125-189. b) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534; c) L. F. Newcomb, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 4993-4994; d) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; e) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324; f) J. P. Glusker, Topics in Current Chemistry 1998, 198, 1-109; g) G. W. Gokel, S. L. De Wall, E. S. Meadows, Eur. J. Org. Chem. 2000, 2967-2978; h) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669. i) McKay, S. L.; Haptonstall, B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 1244-1245. j) V. G. S. Box, F. Jean-Mary, J. Mol. Mod. 2001, 7, 334-342.
58. Aromatic rings can interact with diverse chemical functionalities through a variety of intermolecular forces (hydrogen bond, hydrophobic interactions, electrostatic interactions, and so on), that influence on their structures, physical and biological properties; for some reviews and leading references, see: a) S. K. Burley, G. A. Petsko, Adv. Protein Chem. 1988, 39, 125-189. b) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534; c) L. F. Newcomb, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 4993-4994; d) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; e) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324; f) J. P. Glusker, Topics in Current Chemistry 1998, 198, 1-109; g) G. W. Gokel, S. L. De Wall, E. S. Meadows, Eur. J. Org. Chem. 2000, 2967-2978; h) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669. i) McKay, S. L.; Haptonstall, B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 1244-1245. j) V. G. S. Box, F. Jean-Mary, J. Mol. Mod. 2001, 7, 334-342.
59. Aromatic rings can interact with diverse chemical functionalities through a variety of intermolecular forces (hydrogen bond, hydrophobic interactions, electrostatic interactions, and so on), that influence on their structures, physical and biological properties; for some reviews and leading references, see: a) S. K. Burley, G. A. Petsko, Adv. Protein Chem. 1988, 39, 125-189. b) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534; c) L. F. Newcomb, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 4993-4994; d) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; e) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324; f) J. P. Glusker, Topics in Current Chemistry 1998, 198, 1-109; g) G. W. Gokel, S. L. De Wall, E. S. Meadows, Eur. J. Org. Chem. 2000, 2967-2978; h) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669. i) McKay, S. L.; Haptonstall, B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 1244-1245. j) V. G. S. Box, F. Jean-Mary, J. Mol. Mod. 2001, 7, 334-342.
60. Aromatic rings can interact with diverse chemical functionalities through a variety of intermolecular forces (hydrogen bond, hydrophobic interactions, electrostatic interactions, and so on), that influence on their structures, physical and biological properties; for some reviews and leading references, see: a) S. K. Burley, G. A. Petsko, Adv. Protein Chem. 1988, 39, 125-189. b) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534; c) L. F. Newcomb, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 4993-4994; d) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; e) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324; f) J. P. Glusker, Topics in Current Chemistry 1998, 198, 1-109; g) G. W. Gokel, S. L. De Wall, E. S. Meadows, Eur. J. Org. Chem. 2000, 2967-2978; h) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669. i) McKay, S. L.; Haptonstall, B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 1244-1245. j) V. G. S. Box, F. Jean-Mary, J. Mol. Mod. 2001, 7, 334-342.
61. Aromatic rings can interact with diverse chemical functionalities through a variety of intermolecular forces (hydrogen bond, hydrophobic interactions, electrostatic interactions, and so on), that influence on their structures, physical and biological properties; for some reviews and leading references, see: a) S. K. Burley, G. A. Petsko, Adv. Protein Chem. 1988, 39, 125-189. b) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534; c) L. F. Newcomb, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 4993-4994; d) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; e) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324; f) J. P. Glusker, Topics in Current Chemistry 1998, 198, 1-109; g) G. W. Gokel, S. L. De Wall, E. S. Meadows, Eur. J. Org. Chem. 2000, 2967-2978; h) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669. i) McKay, S. L.; Haptonstall, B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 1244-1245. j) V. G. S. Box, F. Jean-Mary, J. Mol. Mod. 2001, 7, 334-342.
62. Aromatic rings can interact with diverse chemical functionalities through a variety of intermolecular forces (hydrogen bond, hydrophobic interactions, electrostatic interactions, and so on), that influence on their structures, physical and biological properties; for some reviews and leading references, see: a) S. K. Burley, G. A. Petsko, Adv. Protein Chem. 1988, 39, 125-189. b) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534; c) L. F. Newcomb, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 4993-4994; d) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; e) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324; f) J. P. Glusker, Topics in Current Chemistry 1998, 198, 1-109; g) G. W. Gokel, S. L. De Wall, E. S. Meadows, Eur. J. Org. Chem. 2000, 2967-2978; h) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669. i) McKay, S. L.; Haptonstall, B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 1244-1245. j) V. G. S. Box, F. Jean-Mary, J. Mol. Mod. 2001, 7, 334-342.
63. Aromatic rings can interact with diverse chemical functionalities through a variety of intermolecular forces (hydrogen bond, hydrophobic interactions, electrostatic interactions, and so on), that influence on their structures, physical and biological properties; for some reviews and leading references, see: a) S. K. Burley, G. A. Petsko, Adv. Protein Chem. 1988, 39, 125-189. b) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534; c) L. F. Newcomb, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 4993-4994; d) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; e) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324; f) J. P. Glusker, Topics in Current Chemistry 1998, 198, 1-109; g) G. W. Gokel, S. L. De Wall, E. S. Meadows, Eur. J. Org. Chem. 2000, 2967-2978; h) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669. i) McKay, S. L.; Haptonstall, B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 1244-1245. j) V. G. S. Box, F. Jean-Mary, J. Mol. Mod. 2001, 7, 334-342.
64. For general overviews on the design of protease inhibitors, see: a) H.-H. Otto, T. Schirmeister, Chem. Rev. 1997, 97, 133-171; b) A. Albeck, Drug. Dev. Res. 2000, 50, 425-434;
65. For general overviews on the design of protease inhibitors, see: a) H.-H. Otto, T. Schirmeister, Chem. Rev. 1997, 97, 133-171; b) A. Albeck, Drug. Dev. Res. 2000, 50, 425-434;
66. c) D. Leung, G. Abbenante, D. P. Fairlie, J. Med. Chem. 2000, 43, 305-341.
67. T. G. Sazontova, A. A. Matskevich, Y. V. Arkhipenko, Pathophysiology 1999, 6, 91-102.
68. Y. Huang, K. K. W. Wang, Trends Mol. Med. 2001, 7, 355-362.
69. a) B. C. White, J. M. Sullivan, D. J. DeGracia, B. J. O'Neil, R. W. Neumar, L. I. Grossman, J. A. Rafols, G. S. Krause, J. Neurol. Science 2000, 179, 1-33;
70. b) T. Yamashima, Prog. Neurobiol. 2000, 62, 273-295;
71. c) K. K. W. Wang Trends Neuroscience 2000, 23, 20-26.
72. For an overview of early work, see: a) K. K. W. Wang, P. Yuen, Adv. Pharmacol. 1996, 37, 117-152; For recent references, see: b) S. Chatterjee, Z.-Q. Gu, D. Dunn, M. Tao, K. Josef, R. Tripathy, R. Bihovsky, S. E. Senadhi, T. M. O'Kane, B. A. McKenna, S. Mallya, M. A. Ator, D. Bozyczko-Coyne, R. Siman, J. P. Mallamo, J. Med. Chem. 1998, 41, 2663-2666; c) M. Tao, R. Bihovsky, G. J. Wells, J. P. Mallamo, J. Med. Chem. 1998, 41, 3912-3916; d) R. Tripathy, M. A. Ator, J. P. Mallamo, Biorg. Med. Chem. Lett. 2000, 10, 2315-2319; e) I. O. Donkor, X. Zheng, D. D. Miller, Biorg. Med. Chem. Lett. 2000, 10, 2497-2500; f) G. J. Wells, M. Tao, K. A. Josef, R. Bihovsky, J. Med. Chem. 2001, 44, 3488-3503; g) I. O. Donkor, X. Zheng, J. Han, C. Lacy, D. D. Miller, Bioorg. Med. Chem. Lett. 2001, 11, 1753-1755.
73. For an overview of early work, see: a) K. K. W. Wang, P. Yuen, Adv. Pharmacol. 1996, 37, 117-152; For recent references, see: b) S. Chatterjee, Z.-Q. Gu, D. Dunn, M. Tao, K. Josef, R. Tripathy, R. Bihovsky, S. E. Senadhi, T. M. O'Kane, B. A. McKenna, S. Mallya, M. A. Ator, D. Bozyczko-Coyne, R. Siman, J. P. Mallamo, J. Med. Chem. 1998, 41, 2663-2666; c) M. Tao, R. Bihovsky, G. J. Wells, J. P. Mallamo, J. Med. Chem. 1998, 41, 3912-3916; d) R. Tripathy, M. A. Ator, J. P. Mallamo, Biorg. Med. Chem. Lett. 2000, 10, 2315-2319; e) I. O. Donkor, X. Zheng, D. D. Miller, Biorg. Med. Chem. Lett. 2000, 10, 2497-2500; f) G. J. Wells, M. Tao, K. A. Josef, R. Bihovsky, J. Med. Chem. 2001, 44, 3488-3503; g) I. O. Donkor, X. Zheng, J. Han, C. Lacy, D. D. Miller, Bioorg. Med. Chem. Lett. 2001, 11, 1753-1755.
74. For an overview of early work, see: a) K. K. W. Wang, P. Yuen, Adv. Pharmacol. 1996, 37, 117-152; For recent references, see: b) S. Chatterjee, Z.-Q. Gu, D. Dunn, M. Tao, K. Josef, R. Tripathy, R. Bihovsky, S. E. Senadhi, T. M. O'Kane, B. A. McKenna, S. Mallya, M. A. Ator, D. Bozyczko-Coyne, R. Siman, J. P. Mallamo, J. Med. Chem. 1998, 41, 2663-2666; c) M. Tao, R. Bihovsky, G. J. Wells, J. P. Mallamo, J. Med. Chem. 1998, 41, 3912-3916; d) R. Tripathy, M. A. Ator, J. P. Mallamo, Biorg. Med. Chem. Lett. 2000, 10, 2315-2319; e) I. O. Donkor, X. Zheng, D. D. Miller, Biorg. Med. Chem. Lett. 2000, 10, 2497-2500; f) G. J. Wells, M. Tao, K. A. Josef, R. Bihovsky, J. Med. Chem. 2001, 44, 3488-3503; g) I. O. Donkor, X. Zheng, J. Han, C. Lacy, D. D. Miller, Bioorg. Med. Chem. Lett. 2001, 11, 1753-1755.
75. For an overview of early work, see: a) K. K. W. Wang, P. Yuen, Adv. Pharmacol. 1996, 37, 117-152; For recent references, see: b) S. Chatterjee, Z.-Q. Gu, D. Dunn, M. Tao, K. Josef, R. Tripathy, R. Bihovsky, S. E. Senadhi, T. M. O'Kane, B. A. McKenna, S. Mallya, M. A. Ator, D. Bozyczko-Coyne, R. Siman, J. P. Mallamo, J. Med. Chem. 1998, 41, 2663-2666; c) M. Tao, R. Bihovsky, G. J. Wells, J. P. Mallamo, J. Med. Chem. 1998, 41, 3912-3916; d) R. Tripathy, M. A. Ator, J. P. Mallamo, Biorg. Med. Chem. Lett. 2000, 10, 2315-2319; e) I. O. Donkor, X. Zheng, D. D. Miller, Biorg. Med. Chem. Lett. 2000, 10, 2497-2500; f) G. J. Wells, M. Tao, K. A. Josef, R. Bihovsky, J. Med. Chem. 2001, 44, 3488-3503; g) I. O. Donkor, X. Zheng, J. Han, C. Lacy, D. D. Miller, Bioorg. Med. Chem. Lett. 2001, 11, 1753-1755.
76. For an overview of early work, see: a) K. K. W. Wang, P. Yuen, Adv. Pharmacol. 1996, 37, 117-152; For recent references, see: b) S. Chatterjee, Z.-Q. Gu, D. Dunn, M. Tao, K. Josef, R. Tripathy, R. Bihovsky, S. E. Senadhi, T. M. O'Kane, B. A. McKenna, S. Mallya, M. A. Ator, D. Bozyczko-Coyne, R. Siman, J. P. Mallamo, J. Med. Chem. 1998, 41, 2663-2666; c) M. Tao, R. Bihovsky, G. J. Wells, J. P. Mallamo, J. Med. Chem. 1998, 41, 3912-3916; d) R. Tripathy, M. A. Ator, J. P. Mallamo, Biorg. Med. Chem. Lett. 2000, 10, 2315-2319; e) I. O. Donkor, X. Zheng, D. D. Miller, Biorg. Med. Chem. Lett. 2000, 10, 2497-2500; f) G. J. Wells, M. Tao, K. A. Josef, R. Bihovsky, J. Med. Chem. 2001, 44, 3488-3503; g) I. O. Donkor, X. Zheng, J. Han, C. Lacy, D. D. Miller, Bioorg. Med. Chem. Lett. 2001, 11, 1753-1755.
77. For an overview of early work, see: a) K. K. W. Wang, P. Yuen, Adv. Pharmacol. 1996, 37, 117-152; For recent references, see: b) S. Chatterjee, Z.-Q. Gu, D. Dunn, M. Tao, K. Josef, R. Tripathy, R. Bihovsky, S. E. Senadhi, T. M. O'Kane, B. A. McKenna, S. Mallya, M. A. Ator, D. Bozyczko-Coyne, R. Siman, J. P. Mallamo, J. Med. Chem. 1998, 41, 2663-2666; c) M. Tao, R. Bihovsky, G. J. Wells, J. P. Mallamo, J. Med. Chem. 1998, 41, 3912-3916; d) R. Tripathy, M. A. Ator, J. P. Mallamo, Biorg. Med. Chem. Lett. 2000, 10, 2315-2319; e) I. O. Donkor, X. Zheng, D. D. Miller, Biorg. Med. Chem. Lett. 2000, 10, 2497-2500; f) G. J. Wells, M. Tao, K. A. Josef, R. Bihovsky, J. Med. Chem. 2001, 44, 3488-3503; g) I. O. Donkor, X. Zheng, J. Han, C. Lacy, D. D. Miller, Bioorg. Med. Chem. Lett. 2001, 11, 1753-1755.
78. For an overview of early work, see: a) K. K. W. Wang, P. Yuen, Adv. Pharmacol. 1996, 37, 117-152; For recent references, see: b) S. Chatterjee, Z.-Q. Gu, D. Dunn, M. Tao, K. Josef, R. Tripathy, R. Bihovsky, S. E. Senadhi, T. M. O'Kane, B. A. McKenna, S. Mallya, M. A. Ator, D. Bozyczko-Coyne, R. Siman, J. P. Mallamo, J. Med. Chem. 1998, 41, 2663-2666; c) M. Tao, R. Bihovsky, G. J. Wells, J. P. Mallamo, J. Med. Chem. 1998, 41, 3912-3916; d) R. Tripathy, M. A. Ator, J. P. Mallamo, Biorg. Med. Chem. Lett. 2000, 10, 2315-2319; e) I. O. Donkor, X. Zheng, D. D. Miller, Biorg. Med. Chem. Lett. 2000, 10, 2497-2500; f) G. J. Wells, M. Tao, K. A. Josef, R. Bihovsky, J. Med. Chem. 2001, 44, 3488-3503; g) I. O. Donkor, X. Zheng, J. Han, C. Lacy, D. D. Miller, Bioorg. Med. Chem. Lett. 2001, 11, 1753-1755.
79. [24b-d] this strategy has not been employed for calpain inhibition
80. b) W. R. Roush, S. L. Gwaltney II, J. Cheng, K. A. Scheidt, J. H. McKerrow, E. Hansell, J. Am. Chem. Soc. 1998, 120, 10994-10995;
81. c) M. T. Reetz, C. Merk, G. Mehler, Chem. Commun. 1998, 2075-2076;
82. d) J. E. Olson, G. K. Lee, A. Semenov, P. J. Rosenthal, Bioorg. Med. Chem. 1999, 7, 635-638.
83. E. Mann, PhD thesis, University Autónoma (Madrid, Spain), 2002.
84. S. J. Hubbard, J. M. Thornton, S. F. Campbell, Faraday Discuss. 1992, 93, 13-23.
85. All the yields refer to isolated, chromatographically homogeneous, compounds; and have not been optimized. The details of the synthesis of the peptide-heterocycle hybrids (structures of products, yields, and starting peptides) are indicated in Figures 3 and 5 as well as in the Experimental Section.
86. T. Ray, in Handbook of Reagents for Organic Synthesis. Activating Agents and Protecting Groups, (Eds.: A. J. Pearson, W. R. Roush), John Wiley and Sons, Chichester, 1999, pp. 243-244.
87. 2H);
88. b) In some cases, we have used D-amino acids in order to render these compounds more resistant to proteases; for work on D-/L-alternating peptides, see: D. U. Römer, E. Fenude-Schoch, G. P. Lorenzi, H. Rüegger, Helv. Chim. Acta 1993, 76, 451-458; and references cited therein.
89. B. Lygo, in Handbook of Reagents for Organic Synthesis. Activating Agents and Protecting Groups, (Eds.: A. J. Pearson, W. R. Roush), John Wiley and Sons, Chichester, 1999, pp 220-222.
90. K. Jones in Handbook of Reagents for Organic Synthesis. Activating Agents and Protecting Groups (Eds.: A. J. Pearson, W. R. Roush), John Wiley and Sons, Chichester, 1999, pp 318-322.
91. [25] The numbering in the assignation refers to the heterocyclic fragment. When a molecule contains several identical amino acid fragments, they are differentiated by giving the lower number to the one closer to the heterocyclic moiety. The acronyms Miq, Iiq, and Piq are used for the acyl radicals from 4, 5, and 13, respectively. Nva and Phg indicate residues of norvaline and phenylglycine, respectively. The rest of the amino acids are denoted by the standard three-letters code.
92. 3 in a Tris-HCl buffer). The reactions were monitored fluorometrically using a Perkin-Elmer LS50B spectrometer, setting the excitation and emission wavelengths at 485 nm and 530 nm, respectively.
93. a) S.-T. Jiang, J.-H. Wang, T. Chang, C.-S. Chen, Anal. Biochem. 1997, 244, 233-238;
94. b) S. K. Mallya, S. Meyer, D. Bozyczko-Coyne, R. Siman, M. A. Ator, Biochem. Biophys. Res. Comm. 1998, 248, 293-296.