Peptide-heterocycle hybrid molecules: Solid-phase synthesis of a 400-member library of N-terminal 2-iminohydantoin peptides

Journal of Combinatorial Chemistry

Volumn 8, Issue 2, 2006, Pages 237-246

  Gavrilyuk, Julia I ^a   Evindar, Ghotas ^a   Batey, Robert A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; HYDANTOIN DERIVATIVE; IMINE; OLIGOPEPTIDE; PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

HETEROCYCLIC COMPOUNDS; HYDANTOINS; IMINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PEPTIDES;

EID: 33645510651     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc050090+     Document Type: Article

References (71)

1. Sewald, N.; Jakubke, H. D. Peptides: Chemistry and Biology; Wiley-VCH: Weinheim, Germany, 2002.
2. For general reviews, see: (a) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441-452.
3. (b) Bursavich, M. G.; Rich, D. H. J. Med. Chem. 2002, 45, 541-558.
4. (c) Hardy, L. W.; Abraham, D. J.; Safo, M. K. Structure-Based Drug Design and Estiarte, M. A.; Rich, D. H. Peptidomimetics for Drug Design. In Burger's Medicinal Chemistry and Drug Discovery, Vol. 1: Drug Discovery, 6th ed.; Abraham, D. J., Ed.; John Wiley and Sons: Hoboken, New Jersey, 2003; pp 417-469 and 633-685.
5. (d) Loughlin, W. A.; Tyndall, J. D. A.; Glenn, M. P.; Fairlie, D. P. Chem. Rev. 2004, 104, 6085-6117.
6. (a) Hruby, V. J.; Balse, P. M. Curr. Med, Chem. 2000, 7, 945-970.
7. (b) Hruby, V. J. Nat. Rev. Drug Discov. 2002, 1, 847-858.
8. (c) Jones, R. M.; Boatman, P. D.; Semple, G.; Shin, Y.-J.; Tamura, S. Y. Curr. Opin. Pharmacol. 2003, 3, 530-543.
9. (d) Eguchi, M. Med. Res. Rev. 2004, 24, 182-212.
10. (e) Rosenstrom, U.; Skold, C.; Pluoffe, B.; Beaudry, H.; Lindeberg, G.; Botros, M.; Nyberg, F.; Wolf, G.; Karlen, A.; Gallo-Payet, N.; Hallberg, A. J. Med. Chem. 2005, 48, 4009-4024.
11. (a) Cochran, A. G. Curr. Opin. Chem. Biol. 2001, 5, 654-659.
12. (b) Burgess, K. Acc. Chem. Res. 2001, 34, 826-835.
13. (c) Berg, T. Angew. Chem., Int. Ed. 2003, 42, 2462-2481.
14. (d) Pagliaro, L.; Felding, J.; Audouze, K.; Nielsen, S. J.; Terry, R. B.; Krog-Jensen, C.; Butcher, S. Curr. Opin. Chem. Biol. 2004, 8, 442-449.
15. (e) Arkin, M. R.; Wells, J. A. Nat. Rev. Drug Discov. 2004, 3, 301-317.
16. (f) Arkin, M. Curr. Opin. Chem. Biol. 2005, 9, 317-324.
17. (a) Zhang, H.-C.; Andrade-Gordon, P.; Maryanoff, B. E.; Derian, C. K. Drug Dev. Res. 2003, 59, 355-366.
18. (b) Fairlie, D. P. Aust. J. Chem. 2004, 57, 855-857.
19. (a) Stigers, K. D.; Soth, M. J.; Nowick, J. S. Curr. Opin. Chem. Biol. 1999, 3, 714-723.
20. (b) Dasgupta, F.; Gangadhar, N.; Bruhaspathy, M.; Verma, A. K.; Sarin, S.; Mukherjee, A. K. Bioorg. Med. Chem. Lett. 2001, 555-557.
21. (c) Alluri, P. G.; Reddy, M. M.; Bachhawat-Sikder, K.; Olivos, H. J.; Kodadek, T. J. Am. Chem. Soc. 2003, 125, 13995-14004.
22. (d) Horton, D. A.; Severinsen, R.; Koford-Hansen, M.; Bourne, G. T.; Smythe, M. L. J. Comb. Chem. 2005, 7, 421-435.
23. For general review, see: Sewald, N.; Jakubke, H.-D. Peptide and Protein design, Pseudopeptides, and Peptidomimetics. In Peptides: Chemistry and Biology, Wiley-VCH: Weinheim, Germany, 2002, pp 339-378.
24. Peptidomimetics containing heterocyclic cores have received special attention because of their metabolic stability and biological activity, see: (a) Fruchel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
25. (b) Franzen, G. R. J. Comb. Chem. 2000, 2, 195-214.
26. (a) Zabrocki, J.; Dunbar, J. B.; Marshall, K. W.; Toth, M. V.; Marshall, G. R. J. Org. Chem. 1992, 57, 202-209.
27. (b) Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457.
28. (c) Tornoe, C. W.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H.; Meldal, M. J. Comb. Chem. 2004, 6, 312-324.
29. (a) Tamura, S. Y.; Shamblin, B. M.; Brunck, T. K.; Ripka, W. C. Bioorg. Med. Chem. Lett. 1997, 13599-1364.
30. (b) Costanzo, M. J.; Almond, H. R., Jr.; Hecker, L. R.; Schott, M. R.; Yabut, S. C.; Zhang, H.-C.; Andrade-Gordon, P.; Corcoran, T. W.; Giardino, E. C.; Kauffman, J. A.; Lewis, J. M.; de Garavilla, L.; Haertlein, B. J.; Maryanoff, B. E. J. Med. Chem. 2005, 48, 1984-2008.
31. (a) McCornsey, D. F.; Hawkins, M. J.; Andrade-Gordon, P.; Addo, M. F.; Oksenberg, D.; Maryanoff, B. E. Bioorg. Med. Chem. Lett. 1999, 9, 1423-1428.
32. (b) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Comb. Chem. 2002, 4, 484-490.
33. (c) Mann, E.; Ghana, A.; Sanchez-Sancho, F.; Puerta, C.; Garcia-Merino, A.; Herradon, B. Adv. Synth. Catal. 2002, 344, 855-867.
34. (d) Salgado, A.; Mann, E.; Sanchez-Sancho, F.; Herradon, B. Heterocycles 2003, 60, 57-71.
35. (a) Kwon, C-H.; Iqbal, M. T.; Wurpel, J. N. D. J. Med. Chem. 1991, 34, 1845-1849.
36. (b) Sun, Z.-Y.; Kwon, C-H.; Wurpel, J. N. D. J. Med. Chem. 1994, 37, 2841-2845.
37. (c) Rung, C-H.; Wurpel, J. N. D.; Kwon, C.-H. Drug Dev. Res. 1999, 47, 17-26.
38. (a) Dyrant, G. J. Chem. Soc. Rev. 1985, 84, 375-381.
39. (b) Yu, Y.; Ostersh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 3138-3141.
40. (a) Jones, G. L.; Woodbury, D. M. Drug Dev. Res. 1982, 2, 333-335.
41. (b) Poupaert, J. H.; Vandervorst, D.; Guiot, P.; Moustafa, M. M.; Dumont, P. J. Med. Chem. 1984, 27, 76-78.
42. (b) Cortes, S.; Liao, Z.-K.; Watson, D.; Kohn, H. J. Med. Chem. 1985, 28, 601-606.
43. (d) Meusel, M.; Gutschow, M. Org. Prep. Proc. Intl. 2004, 36, 391-443.
44. (a) Wegner, M. M.; Rapoport, H. J. Org. Chem. 1978, 43, 3840-3844.
45. (b) Kwon, C. H.; Nagasawa, H. T. Synth. Commun. 1987, 17, 1677-1682.
46. (c) Talaty, E. R.; Gomez, J. A.; Dillon, J. A.; Palomino, E.; Agho, M. O.; Batt, B. C.; Gleason, K. J.; Park, S.; Hernandez, J. R.; Yusoff, M. M.; Rupp, G. A.; Malone, F. C.; Brummett, M. F.; Finch, C. L.; Ismail, S. A.; Williams, N.; Aghakhani, M. Synth. Commun. 1987, 17, 1063-1070.
47. (d) Bentley, J. D.; Maclaren, J. A. Aust. J. Chem. 1991, 44, 537-442.
48. (e) Garratt, P. J.; Thorn, S. N.; Wrigglesworth, R. Tetrahedron Lett. 1991, 32, 691-694.
49. (f) Garratt, P. J.; Thorn, S. N.; Wrigglesworth, R. Tetrahedron 1993, 49, 6885-6898.
50. (g) Ding, M.-W.; Tu, H.-Y.; Liu, Z.-J. Synth. Commun. 1997, 27, 3657-3662.
51. (h) Drewry, D. H.; Ghiron, C. Tetrahedron Lett. 2000, 41, 6989-6992.
52. Evindar, G.; Batey, R. A. Org. Lett. 2003, 5, 1201-1204.
53. Yu, Y.; Ostresh, J. M.; Houghten, R. A. Tetrahedron 2002, 58, 3349-3353.
54. (a) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Comb. Chem. 2001, 3, 521-523.
55. (b) Lange, U. E. W. Tetrahedron Lett. 2002, 43, 6857-6860.
56. (c) Li, J.; Zhang, Z.; Fan, E. Tetrahedron Lett. 2004, 45, 1267-1269.
57. (a) Edman, P. Acta Chem. Scand. 1950, 4, 283-293.
58. (b) Edman, P.; Begg, G. Eur. J. Biochem. 1967, 1, 80-91.
59. N-terminal cyclization of peptides to hydantoins and thiohydantoins has been achieved by reaction of peptides with N,N′-carbonyldiimidazole and N,N′-thiocarbonyldiimidazole, respectively. Esser, F.; Roos, O. Angew. Chem. 1978, 90, 495-496;
60. Angew. Chem., Int. Ed. Engl. 1978, 17, 467-468.
61. For general references on solid-phase organic synthesis, see: (a) Fruchel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
62. (b) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
63. Krchnak, V.; Holladay, M. W. Chem. Rev. 2002, 102, 61-91.
64. (a) Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiu, G.; Sotiriu, P.; Yao, W.; Schaefer, W. Tetrahedron Lett. 1989, 30, 3943-3946.
65. (b) Barlos, K.; Chatzi, O.; Gatos, D.; Stavropoulos, G. Int. J. Pept. Protein Res. 1991, 37, 513-520.
66. (c) Barlos, K.; Gatos, D.; Kapolos, S.; Poulos, C.; Schafer, W.; Yao, W. Int. J. Pept. Protein Res. 1991, 38, 555-561.
67. (d) Barlos, K.; Gatos, D.; Kutsogianni, S.; Papaphotiou, G.; Poulos, C.; Tsegenidis, T. Int. J. Pept. Protein Res. 1991, 38, 562-568.
68. Barlos, K.; Gatos, D.; Kapolos, S.; Papaphotiu, G.; Schaefer, W.; Yao, W. Tetrahedron Lett. 1989, 30, 3947-3950.
69. Houghten, R. A. Proc. Natl. Acad. Sci. U.S.A., 1985, 82, 5131-5135.
70. Bollhagen, R.; Schmiedberger, M.; Barlos, K.; Grell, E. J. Chem. Soc., Chem. Commun. 1994, 2559-2560.
71. NovaBiochem Catalog 2000, Synthesis Notes, P4, Method 6P.