Synthesis and structure of 1,4-dipiperazino benzenes: Chiral terphenyl-type peptide helix mimetics

Organic Letters

Volumn 10, Issue 7, 2008, Pages 1473-1476

  Maity, Prantik ^a   König, Burkhard ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; PEPTIDE; TERPHENYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; MOLECULAR MIMICRY; PROTEIN SECONDARY STRUCTURE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BENZENE DERIVATIVES; CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; TERPHENYL COMPOUNDS;

EID: 45849130968     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8002749     Document Type: Article

References (68)

1. (a) Kabsch, W.; Sander, C. Biopolymers 1983, 22, 2577-2637.
2. (b) Ruan, F.Q.; Chen, Y. Q.; Hopkins, P. B. J. Am. Chem. Soc. 1990, 112, 9403-9404.
3. (a) Cochran, A. G. Chem. Biol. 2000, 7, 85-89.
4. (b) Cochran, A. G. Curr. Opin. Chem. Biol. 2001, 5, 654-659.
5. (a) Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6568-6570.
6. (b) Gennari, G.; Salom, B.; Potenza, D.; Williams, A. Angew. Chem., Int. Ed. Engl. 1994, 33, 2067-2069.
7. (c) Gude, M.; Piarulli, U.; Potenza, D.; Salom, B.; Gennari, C. Tetrahedron Lett. 1996, 37, 8589-8592.
8. (d) Cho, C. Y.; Moran, E. J.; Cherry, S. R.; Stephans, J. C.; Fodor, S. P. A.; Adams, C. L.; Sundaram, A.; Jacobs, J. W.; Schultz, P. G. Science 1993, 261, 1303-1305.
9. (e) Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1996, 118, 7529-7541.
10. (f) Nowick, J. S.; Mahrus, S.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 1066-1072.
11. (g) Lokey, R. S.; Iverson, B. L. Nature 1995, 375, 303-305.
12. (h) Murray, T. J.; Zimmerman, S. C. J. Am. Chem. Soc. 1992, 114, 4010-4011.
13. (i) Antuch, W.; Menon, S.; Chen, Q.-Z.; Lu, Y.; Sakamuri, S.; Beck, B.; Schauer-Vukasinovic, V.; Agarwal, S.; Hess, S.; Domling, A. Bioorg. Med. Chem. Lett. 2006, 16, 1740-1743.
14. For reviews on R-helix mimetics, see: (j) Yin, H.; Hamilton, A. D. Angew. Chem., Int. Ed. 2005, 44, 4130-4163.
15. (k) Maity, P.; König, B. Pept. Sci. 2008, 90, 8-27.
16. (l) Davis, J. M.; Tsou, L. K.; Hamilton, A. D. Chem. Soc. Rev. 2007, 36, 326-334.
17. See also: (m) Cummings, M. D.; Schubert, C.; Parks, D. J.; Calvo, R. R.; Lafrance, L. V.; Lattanze, J.; Milkiewicz, K. L.; Tianbao, L. Chem. Biol. Drug Des. 2006, 67, 201-205.
18. (n) Ahn, J.-M.; Han, S.-Y. Tetrahedron Lett. 2007, 48, 3543-3547.
19. (o) Walensky, L. D.; Kung, A. L.; Escher, I.; Malia, T. J.; Barbuto, S.; Wright, R. D.; Wagner, G.; Verdine, G. L.; Korsmeyer, S. J. Science 2004, 305, 1466-1470.
20. (a) Fairlie, D. P.; West, M. L.; Wong, A. K. Curr. Med. Chem. 1998, 5, 29-62.
21. (b) Jain, R.; Ernst, J. T.; Kutzuki, O.; Park, H. S.; Hamilton, A. D. Mol. Diversity 2004, 8, 89-100.
22. (c) Zutshi, R.; Brickner, M.; Chmielewski, J. Curr. Opin. Chem. Biol. 1998, 2, 62-66.
23. (d) Berg, T. Angew. Chem., Int. Ed. 2003, 42, 2462-2481.
24. Xuereb, H.; Maletic, M.; Glidersleeve, J.; Pelczer, I.; Kahne, D. J. Am. Chem. Soc. 2000, 122, 1883-1884.
25. Raguse, T. L.; Kai, J. R.; Gellman, S. H. J. Am. Chem. Soc. 2003, 125, 5592-5593.
26. Kritzer, J. A.; Lear, J. D.; Hodsdon, M. E.; Schepartz, A. J. Am. Chem. Soc. 2004, 126, 9468-9469.
27. (a) Orner, B. P.; Ernst, J. T.; Hamilton, A. D. J. Am. Chem. Soc. 2001, 123, 5382-5383.
28. (b) Yin, H.; Lee, G.; Sedey, K. A.; Kutzki, O.; Park, H. S.; Orner, B. P.; Ernst, J. T.; Wang, H.-G.; Sebti, S. M.; Hamilton, A. D. J. Am. Chem. Soc. 2005, 127, 10191-10196.
29. (c) Yin, H.; Lee, G.; Park, H. S.; Payne, G. A.; Rodriguez, J. M.; Sebti, S. M.; Hamilton, A. D. Angew. Chem., Int. Ed. 2005, 44, 2704-2707.
30. (d) Ernst, J. T.; Becerill, J.; Park, H. S.; Yin, H.; Hamilton, A. D. Angew. Chem., Int. Ed. 2003, 42, 535-539.
31. (e) Yin, H.; Hamilton, A. D. Bioorg. Med. Chem. Lett. 2004, 14, 1375-1379.
32. (f) Davis, J. M.; Truong, A.; Hamilton, A. D. Org. Lett. 2005, 7, 5405-5408.
33. (g) Kim, I. C.; Hamilton, A. D. Org. Lett. 2006, 8, 1751-1754.
34. Rodriguez, J. M.; Hamilton, A. D. Angew. Chem., Int. Ed. 2007, 46, 8614-8617.
35. Volonterio, A.; Molsan, L.; Rebek, J., Jr. Org. Lett. 2007, 9, 3733-3736.
36. (b) Biros, S. M.; Molsan, L.; Mann, E.; Carella, A.; Zhai, D.; Reed, J. C.; Rebek, J., Jr. Bio. Med. Chem. Lett. 2007, 17, 4641-4645.
37. Spartan '06, Wavefunction, Inc. AM1 semi-empirical geometry optimization.
38. Protein helices derived from natural amino acids are chiral. Many examples from medicinal chemistry show that the interaction of proteins with chiral molecules significantly depends on their chirality: Chirality in Drug Research; Francotte, E., Lindner, W., Eds.; Wiley: New York, 2007; Vol. 33. Methods and Principles in Medicinal Chemistry; Mannhold, R., Kubinyi, H., Folkers, G., Eds.; Wiley-VCH: Weinheim, 2006. 1,4-Dipiperazino benzene helix mimetics with different chirality are therefore expected to interact differently with helix-binding proteins.
39. Liu, B.; Xu, G.-Y.; Yang, C.-H.; Wu, X.-H.; Xie, Y.-Y. Syn. Commun. 2004, 34, 4111-4118.
40. Daugan, A. C.-M. (ICOS Corp.). Tetracyclic derivs., process of preparation and use. EP 0740668.
41. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793-796.
42. (a) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453-2455.
43. (b) Cai, Q.; Zhu, W.; Zhang, H.; Zhang, Y.; Ma, D. Synthesis 2005, 496-499.
44. (c) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164 -5173.
45. (d) Application in drug synthesis: Egger, M.; Li, X.; Müller, C.; Bernhardt, G.; Buschauer, A.; König, B. Eur. J. Org. Chem. 2007, 2643-2649.
46. (a) Lu, Z.; Twieg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 6289-6292.
47. (b) Lu, Z.; Twieg, R. J. Tetrahedron 2005, 61, 903-918.
48. Zhu, D.; Wang, R.; Mao, J.; Xu, L.; Wu, F.; Wan, B. J. Mol. Catal. A: Chem. 2006, 256, 256-260.
49. Shafir, A.; Buchwald, S. J. Am. Chem. Soc. 2006, 128, 8742-8743.
50. Jiang, D.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2007, 72, 672-674.
51. Marinetti, A.; Hubert, P.; Genet, J.-P. Eur. J. Org. Chem. 2000, 1815-1820
52. (a) Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927-928.
53. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
54. (c) An example of an intramolecular carbon-nitrogen bond forming process which proceeds at room temperature has been reported: Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525-7546.
55. (d) Wolfe, J. P.; Wagaw. S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216.
56. (e) Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240-7241.
57. (f) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609-3612.
58. (g) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218.
59. (h) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133-1135.
60. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264-1267.
61. (j) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268-1273.
62. (k) Subat, M.; König, B. Synthesis 2001, 1818-1825.
63. (l) For, a review, see: Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
64. (m) For two-fold amination, see: Tasler, S.; Mies, J.; Lang, M. Adv. Synth. Catal. 2007, 349, 2286-2300.
65. (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
66. (b) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158-1174.
67. (c) Charles, M. D.; Schultz, P.; Buchwald, S. L. Org. Lett. 2005, 7, 3965-3968.
68. (d) Anderson, K. W.; Tundel, R. E.; Ikawa, T.; Altman, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 6523-6527.