Synthesis of a C3-symmetric furyl-cyclopeptide platform with anion recognition properties

European Journal of Organic Chemistry

Volumn , Issue 21, 2010, Pages 4049-4055

  Molina, Lidia ^a   Moreno Clavijo, Elena ^a   Moreno Vargas, Antonio J ^a   Carmona, Ana T ^a   Robina, Inmaculada ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

Anion receptors; Cyclopeptides; Heterocycles; Host guest systems; Peptidomimetics

Indexed keywords

EID: 77954708878     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000219     Document Type: Article

References (76)

1. a) S. Kubik, Chem. Soc. Rev. 2009, 38, 585-605, and references cited therein;
2. b) S. O. Kang, R. A. Begum, K. Bowman-James, Angew. Chem. Int. Ed. 2006, 45, 7882-7894;
3. c) T. Gunnlaugsson, M. Glynn, G. M. Tocci, P. E. Kruger, F. M. Pfeffer, Coord. Chem. Rev. 2006, 250, 3094-3117;
4. d) P.A. Gale, Acc. Chem. Res. 2006, 39, 465-475;
5. e) R. J. T. Houk, S. L. Tobey, E. V. Anslyn, Top. Curr. Chem. 2005, 255, 199-229;
6. f) R. Vilar, Eur. J. Inorg. Chem. 2008, 357-367;
7. g) A. Bianchi, K. BowmanJames, E. García-España, in: Supramolecular Chemistry of Anions, Wiley-VCH, New York, 1997;
8. h) P. A. Gale, Coord. Chem. Rev. 2003, 240, 191-221;
9. i) K. Bowman-James, Acc. Chem. Res. 2005, 38, 671-678;
10. j) P. Prados, R. Quesada, Supramol. Chem. 2008, 20, 201-216;
11. k) A. Pinter, G. Haberhauer, Synlett 2009, 3082-3098;
12. l) C. Caltagirone, P. A. Gale, Chem. Soc. Rev. 2009, 38, 520-563;
13. m) G. V. M. Sharma, V. Manohar, S. K. Dutta, B. Sridhar, V. S. Ramesh, K. Ragampeta, C. Ajit, J. Org Chem. 2010, 75, 1087-1094.
14. a) J. M. Berg, Acc. Chem. Res. 1995, 28, 14-19;
15. b) J. D. Puglisi, L. Chen, A. D. Frankel, J. R. Williamson, Prot: Nat. Acad. Sci. USA 1993, 90, 3680-3684.
16. A. D. Burrows, Sci. Prog. 2002, 85, 199-217.
17. a) P. D. Beer, P. A. Gale, Angew. Chem. Int. Ed. 2001, 40, 486-516;
18. b) V. Amendola, D. Esteban-Gómez, L. Fabbrizzi, M. Licchelli, Acc. Chem. Res. 2006, 39, 343-353.
19. a) K. W. Kulig, Cyanide Toxicity, U. S. Department of Health and Human Services, Atlanta, GA, 1991;
20. b) S. I. Baskin, T. G. Brewer, in: Medical Aspects of Chemical and Biological Warfare (Eds.: F. R. Sidell, E. T. Takafuji, D. R. Franz), TMM Publications, Washington, DC, 1997, pp. 271-286;
21. c) C. Baird, M. Cann, Environmental Chemistry, 4th ed, Freeman and Co, New York, 2005.
22. G. C. Miller, C. A. Pritsos, Proc. Symp. Annu, Meet., TMS, 2001, pp. 73-81.
23. a) S. Y. Chung, S.-W. Nam, J. Lim, S. Park, J. Yoon, Chem. Commun. 2009, 2866-2868;
24. b) R.-J. Cheng, C.-H. Lee, C.-W. Chao, Chem. Commun, 2009, 2526-2528;
25. c) S.-J. Hong, J. Yoo, S.-H. Kim, J. S. Kim, J. Yoon, C.-H. Lee, Chem. Commun. 2009, 189-191;
26. d) H. Miyaji, D.-S. Kim, B.-Y. Chang, E. Park, S.-M. Park, K. H. Ahn, Chem. Commun. 2008, 753-755;
27. e) C.L. Chen, Y-H. Chen, C.-Y Chen, S.-S. Sun, Org. Lett, 2006, 8, 5053-5056;
28. f) Y. M. Chung, B. Raman, D.-S. Kim, K. H. Ahn, Chem. Commun. 2006, 186-188;
29. g) M. Tomasulo, S. Sort ino, A. J. P. White, F. M. Raymo, J. Org. Chem. 2006, 71, 744-753;
30. h) M. Tomasolu, F. M. Raymo, Org. Lett. 2005, 7, 4633-4636;
31. i) A. Ajayaghosh, Acc. Chem. Res. 2005, 38, 449-459;
32. j) C.-F. Chow, M. H. W. Lam, W.-Y. Wong, Inorg. Chem. 2004, 43, 8387-8393;
33. k) J. V. Ros-Lis, R. Martínez-Máñez, J. Soto, Chem. Commun. 2002, 2248-2249.
34. a) C. Reyheller, B. P. Hay, S. Kubik, New J. Chem. 2007, 31, 2095-2102;
35. b) C. Reyheller, S. Rubik, Org. Lett. 2007, 9, 5271-5274;
36. c) Z. Rodríguez-Docampo, S. I. Pascu, S. Kubik, S. Otto, J. Am. Chem. Soc. 2006, 128, 11206-11210;
37. d) S.O. Kang, M. A. Hossain, K. Bowman-James, Coord. Chem, Rev. 2006, 250, 3038-3052;
38. e) M. J. Chmielewski, J. Jurezak, Chem. Eur. J. 2005, 11, 6080-6094;
39. f) S. Kubik, C. Reyheller, S. Stuewe, J. Incl. Phenom. Macrocyclic Chem. 2005, 52, 137-187;
40. g) S. Kubik, Highlights Bioorg. Chem. 2004, 51, 124-137;
41. h) S. Otto, S. Kubik, J. Am. Chem. Soc. 2003, 125, 7804-7805;
42. i) S. Kubik, R. Goddard, R. Kirchner, D. Nolting, J. Seidel, Angew. Chem. Int. Ed. 2001, 40, 2648-2651.
43. For selected references, see: a) S. L. You, J. W. Kelly, J. Org. Chem. 2003, 68, 9506-9509;
44. b) S. L. You, J. W. Kelly, Chem. Eur. J. 2004, 10, 71-75;
45. c) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno, D. R. Williams, Org. Lett. 2000, 2, 1165-1168;
46. d) S. L. You, S. Deechongkit, J. W. Kelly, Org. Lett, 2004, 6, 2627-2630;
47. e) G. Pattenden, T. Thompson, Tetrahedron Lett. 2002, 43, 2459-2461;
48. f) J. Deeley, G. Pattenden, Chem. Commun. 2005, 797-799;
49. g) W. Wang, F. Nan, J. Org. Chem. 2003, 68, 1636-1639;
50. h) A. Bertram, N. Maulucci, O. M. New, S. M. M. Nor, G. Pattenden, Org. Biomol. Chem. 2007, 5, 1541-1553.
51. a) R. A. Hughes, C. J. Moody, Angew. Chem. Int. Ed. 2007, 46, 7930-7954;
52. b) T. K. Chakraborty, A. Arora, S. Roy, N. Kumar, S. Maiti, J. Med. Chem. 2007, 50, 5539-5542;
53. c) A. J. MorenoVargas, L. Molina, A. T. Carmona, A. Ferrali, M. Lambelet, O. Spertini, I. Robina, Eur. J. Org. Chem. 2008, 2973-2982;
54. d) Y. Singh, M. J. Stoermer, A. J. Lucke, T. Guthrie, D. P. Fairlie, J. Am. Chem. Soc. 2005, 127, 6563-6572.
55. a) G. Haberhauer, T. Oeser, F. Rominger, Chem. Commun. 2004, 2044-2045;
56. b) G. Haberhauer, T. Oeser, F. Rominger, Chem. Eur. J. 2005, 11, 6718-6726;
57. c) G. Haberhauer, Synlett 2004, 1003-1006.
58. a) L. Somogyi, G. Haberhauer, J. Rebek Jr., Tetrahedron 2001, 57, 1699-1708;
59. b) G. Haberhauer, E. Drosdow, T. Oeser, F. Rominger, Tetrahedron 2008, 64, 1853-1859.
60. a) A. Pintér, G. Haberhauer, Eur. J. Org. Chem, 2008, 2375-2387;
61. b) A. Pintér, G. Haberhauer, Chem, Eur. J. 2008, 14, 11061-11068.
62. a) T. K. Chakraborty, S. Tapadar, S. K. Kumar, Tetrahedron Lett. 2002, 43, 1317-1320;
63. b) T. K. Chakraborty, S. Tapadar, T. V. Raju, J. Annapuma, H. Singh, Synlett. 2004, 2484-2488;
64. c) M. Schnopp, S. Ernst, G. Haberhauer, Eur. J. Org. Chem. 2009, 213-222.
65. a) A. J. Moreno-Vargas, J. G. Fernández-Bolaños, J. Fuentes, I. Robina, Tetrahedron Lett, 2001, 42, 1283-1285;
66. b) A. J. Moreno-Vargas, J. Jiménez-Barbero, I. Robina, J. Org. Chem. 2003, 68, 4138-4150;
67. c) L. Molina, A. J. Moreno-Vargas, A. T. Carmona, I. Robina, Synlett 2006, 1327-1330;
68. d) L. Molina, E. Moreno-Clavijo, A. J. Moreno-Vargas, A. T. Carmona, I. Robina, Eur. J. Org. Chem. 2010, 3110-3119.
69. Due to the aromatic character of the furan-3-carboxylic acid, compound 4 is stable which makes it an attractive building block for peptide synthesis as compared to most OBt esters of Boc amino acids which are not stable enough and need to be generated in situ.
70. a) F. Mohamadi, N. G. I. Richards, W. C. Guida, R. Liskamp, C. Canfield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem, 1990, 11, 440-467.
71. N. L. Allinger, J. Am. Chem. Soc. 1977, 99, 8127-8134.
72. For a similar study in an imidazole-based cyclopeptide, see ref. [11c].
73. T. R. Kelly, M. H. Kim, J. Am. Chem, Soc. 1994, 116, 7072-7080.
74. V. M. S. Gil, N. C. Oliveira, J. Chem. Ed. 1990, 67, 473-4178.
75. For a recent review of C-H hydrogen-bond donors, see: R. K. Castellano, Curr. Org. Chem. 2004, 8, 845-865.
76. V. S. Bryantsev, B. P. Hay, Org. Lett. 2005, 7, 5031-5034.