Design, synthesis, and applications of 3-aza-6,8-dioxabicyclo[3.2.1]octane- based scaffolds for peptidomimetic chemistry

Synlett

Volumn , Issue 3, 2006, Pages 331-353

  Trabocchi, Andrea ^a   Menchi, Gloria ^a   Guarna, Francesco ^a   Machetti, Fabrizio ^a   Scarpi, Dina ^a   Guarna, Antonio ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Combinatorial chemistry; Conformational analysis; Peptides; Peptidomimetics; Solid phase synthesis

Indexed keywords

3 AZA 6,8 DIOXABICYCLO[3.2.1]OCTANE; AMINE; AMINO ACID; BICYCLO COMPOUND; CARBOHYDRATE DERIVATIVE; CARBOXYL GROUP; DIPEPTIDE; KETONE; MONOMER; PEPTIDE; RESIN; SCAFFOLD PROTEIN; SUGAR; TARTARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BIOAVAILABILITY; CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; CONFORMATION; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID PHASE SYNTHESIS; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33344468779     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926249     Document Type: Article

References (101)

1. Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244.
2. Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
3. Adessi, C.; Soto, C. Curr. Med. Chem. 2002, 9, 963.
4. Liskamp, R. M. J. Red. Trav. Chim. Pays-Bas 1994, 113, 1.
5. Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bös, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039.
6. Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
7. Hirschmann, R.; Nicolau, K. C.; Pietranico, S.; Leahy, E. M.; Salvino, J.; Arison, B.; Cichy, M. A.; Spoors, P. G.; Shakespeare, W. C.; Sprengeler, P. A.; Hamley, P.; Smith, A. B. III; Reisine, T.; Raynor, K.; Maechler, L.; Donaldson, C.; Vale, W.; Freidinger, R. M.; Cascieri, M. R.; Strader, C. D. J. Am. Chem. Soc. 1993, 115, 12550.
8. Hirschmann, R.; Sprengeler, P. A.; Kawasaki, T.; Leahy, J. W.; Shakespeare, W. C.; Smith, A. B. III J. Am. Chem. Soc. 1992, 114, 9699.
9. Lam, K. S.; Lebl, M.; Krchňák, V. Chem. Rev. 1997, 97, 411.
10. Dolle, R. E. J. Comb. Chem. 2001, 3, 477.
11. Dolle, R. E. J. Comb. Chem. 2002, 4, 369.
12. Dolle, R. E. J. Comb. Chem. 2003, 5, 693.
13. Dolle, R. E. J. Comb. Chem. 2004, 6, 623.
14. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
15. Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449.
16. Golebiowski, A.; Klopfenstein, S. R.; Shao, X.; Chen, J. J.; Colson, A.-O.; Grieb, A. L.; Russell, A. F. Org. Lett. 2000, 2, 2615.
17. Creighton, C. J.; Zapf, C. W.; Bu, J. H.; Goodman, M. Org. Lett. 1999, 1, 1407.
18. Kim, H. O.; Nakanishi, H.; Lee, M. S.; Kahn, M. Org. Lett. 2000, 2, 301.
19. Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204.
20. Guarna, A.; Guidi, A.; Machetti, F.; Menchi, G.; Occhiato, E. G.; Scarpi, D.; Sisi, S.; Trabocchi, A. J. Org. Chem. 1999, 64, 7347.
21. Cini, N.; Machetti, F.; Menchi, G.; Occhiato, E. G.; Guarna, A. Eur. J. Org. Chem. 2002, 873.
22. Trabocchi, A.; Menchi, G.; Rolla, M.; Machetti, F.; Bucelli, I.; Guarna, A. Tetrahedron 2003, 59, 5251.
23. Trabocchi, A.; Cini, N.; Menchi, G.; Guarna, A. Tetrahedron Lett. 2003, 44, 3489.
24. Guarna, A.; Bucelli, I.; Machetti, F.; Menchi, G.; Occhiato, E. G.; Scarpi, D.; Trabocchi, A. Tetrahedron 2002, 58, 9865.
25. Guarna, A.; Menchi, G.; Machetti, F.; Occhiato, E. G.; Scarpi, D. WO 01/64686, 2001; Chem. Abstr. 2001, 135, 211044.
26. Trabocchi, A.; Mancini, P.; Menchi, G.; Guarna, A. Mol. Diversity 2003, 6, 245.
27. Scarpi, D.; Stranges, D.; Cecchi, L.; Guarna, A. Tetrahedron 2004, 60, 2583.
28. Danieli, E.; Trabocchi, A.; Menchi, G.; Guarna, A. Eur. J. Org. Chem. 2005, 4372.
29. Trabocchi, A.; Rolla, M.; Menchi, G.; Guarna, A. Tetrahedron Lett. 2005, 46, 7813.
30. 2, and subsequent hydrogenation of the benzylic group.
31. 2 treatment was reported for the preparation of BTG. See: Dienes, Z.; Vogel, P. J. Org. Chem. 1996, 61, 6958.
32. Reymond, J.-L.; Vogel, P. J. Chem. Soc., Chem. Commun. 1990, 1070.
33. Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729.
34. Crystallographic data (excluding structure factors) for the structure 110 in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 286087. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].
35. Hanessian, S.; Xie, F. Tetrahedron Lett. 1998, 39, 733.
36. Christensen, T. Acta Chem. Scand., Ser. B 1979, 33, 763.
37. The Bromophenol Blue test is not specific, as it reveals the presence of primary to quaternary amines. See: Krchnák, V.; Vágner, J.; Safár, P.; Lebl, M. Collect. Czech. Chem. Commun. 1988, 53, 2542.
38. Furman, B.; Thürmer, R.; Kaluża, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem. Int. Ed. 1999, 38, 1121.
39. Purandare, A. V.; Poss, M. A. Tetrahedron Lett. 1998, 39, 935.
40. Caputo, R.; Cassano, E.; Longobardo, L.; Palumbo, G. Tetrahedron 1995, 51, 12337.
41. Yan, L. Z.; Mayer, J. P. J. Org. Chem. 2003, 68, 1161.
42. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.
43. 4 as reported. See: Earle, M. J.; Abdur-Rashid, A.; Priestley, N. D. J. Org. Chem. 1996, 61, 5697.
44. Machetti, F.; Bucelli, I.; Indiani, G.; Guarna, A. C. R. Chimie 2003, 6, 631.
45. Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
46. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
47. Machetti, F.; Ferrali, A.; Menchi, G.; Occhiato, E. G.; Guarna, A. Org. Lett. 2000, 2, 3987.
48. Chou, P. Y.; Fasman, G. D. J. Mol. Biol. 1977, 115, 135.
49. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1.
50. Stanfield, R. L.; Fieser, T. M.; Lerner, R. A.; Wilson, I. A. Science 1990, 248, 712.
51. Müller, G.; Hessler, G.; Decornez, H. Y. Angew. Chem. Int. Ed. 2000, 39, 894.
52. Richardson, J. S. Adv. Protein Chem. 1981, 34, 167.
53. Müller, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2767.
54. Belvisi, L.; Gennari, C.; Mielgo, A.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 1999, 389.
55. Halab, L.; Lubell, W. D. J. Org. Chem. 1999, 64, 3312.
56. Halab, L.; Lubell, W. D. J. Am. Chem. Soc. 2002, 124, 2474.
57. Dumas, J.-P.; Germanas, J. P. Tetrahedron Lett. 1994, 35, 1495.
58. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847.
59. Cumberbatch, S.; North, M.; Zagotto, G. Tetrahedron 1993, 49, 9049.
60. An, S. S. A.; Lester, C. C.; Peng, J.-L.; Li, Y.-J.; Rothwarf, D. M.; Welker, E.; Thannhauser, T. W.; Zhang, L. S.; Tam, J. P.; Scheraga, H. A. J. Am. Chem. Soc. 1999, 121, 11558.
61. Keller, M.; Sager, C.; Dumy, P.; Schutkowsky, M.; Fischer, G. S.; Mutter, M. J. Am. Chem. Soc. 1998, 120, 2714.
62. Brady, S. F.; Paleveda, W. J. Jr.; Arison, B. H.; Saperstein, R.; Brady, E. J.; Raynor, K.; Reisine, T.; Veber, D. F.; Freidinger, R. M. Tetrahedron 1993, 49, 3449.
63. Sukumaran, D. K.; Prorok, M.; Lawrence, D. S. J. Am. Chem. Soc. 1991, 113, 706.
64. Zabrocki, J.; Smith, G. D.; Dunbar, J. B. Jr.; Marshall, G. R. J. Am. Chem. Soc. 1988, 110, 5875.
65. Souers, A. J.; Virgilio, A. A.; Schürer, S. S.; Ellman, J. A.; Kogan, T. P.; West, H. E.; Ankener, W.; Vanderslice, P. Bioorg. Med. Chem. Lett. 1998, 8, 2297.
66. Cho, N.; Harada, M.; Imaeda, T.; Imada, T.; Matsumoto, H.; Hayase, Y.; Sasaki, S.; Furuya, S.; Suzuki, N.; Okubo, S.; Ogi, S.; Endo, S.; Onda, H.; Fujino, M. J. Med. Chem. 1998, 41, 4190.
67. Souers, A. J.; Virgilio, A. A.; Rosenquist, Å.; Fenuik, W.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 1817.
68. Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11580.
69. Virgilio, A. A.; Schürer, S. C.; Ellman, J. A. Tetrahedron Lett. 1996, 37, 6961.
70. Virgilio, A. A.; Bray, A. A.; Zhang, W.; Trinh, L.; Snyder, M.; Morissey, M.; Ellman, J. A. Tetrahedron 1997, 53, 6635.
71. Feng, Y.; Wang, Z.; Jin, S.; Burgess, K. J. Am. Chem. Soc. 1998, 120, 10768.
72. Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204.
73. Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647.
74. Feigel, M. J. Am. Chem. Soc. 1986, 108, 181.
75. Diaz, H.; Espina, J. R.; Kelly, J. W. J. Am. Chem. Soc. 1992, 114, 8316.
76. Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778.
77. Jones, I. G.; Jones, W.; North, M. J. Org. Chem. 1998, 63, 1505.
78. Holmes, D. L.; Smith, E. M.; Nowick, J. S. J. Am. Chem. Soc. 1997, 119, 7655.
79. Smith, E. M.; Holmes, D. L.; Shaka, A. J.; Nowick, J. S. J. Org. Chem. 1997, 62, 7906.
80. Nesloney, C. L.; Kelly, J. W. J. Am. Chem. Soc. 1996, 118, 5836.
81. Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280.
82. Schneider, J. P.; Kelly, J. W. J. Am. Chem. Soc. 1995, 117, 2533.
83. Kemp, D. S.; Li, Z. Q. Tetrahedron Lett. 1995, 36, 4179.
84. Gardner, B.; Nanashi, H.; Khan, M. Tetrahedron 1993, 49, 3433.
85. Brandmeier, V.; Feigel, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 486;
86. Angew. Chem. 1989, 102, 466.
87. Nowick, S.; Smith, E. M.; Noronha, G. J. Org. Chem. 1995, 60, 7386.
88. Nagai, U.; Sato, K.; Nakamura, R.; Kato, R. Tetrahedron 1993, 49, 3577.
89. Kemp, D. S.; Sites, W. E. Tetrahedron Lett. 1988, 29, 5057.
90. Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 2303.
91. Krauthäuser, S.; Christianson, L. A.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 11719.
92. Hanessian, S.; Yang, H. Tetrahedron Lett. 1997, 38, 3155.
93. Fink, B. E.; Kym, P. R.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1998, 120, 4334.
94. Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
95. Wishart, D. S.; Sykes, B. D.; Richards, F. M. J. Mol. Biol. 1991, 222, 311.
96. Chang, G.; Guida, W. C.; Still, W. C. J. Comput. Chem. 1994, 15, 1302.
97. Ball, J. B.; Hughes, R. A.; Alewood, P. F.; Andrews, P. R. Tetrahedron 1993, 49, 3467.
98. Scarpi, D.; Occhiato, E. G.; Trabocchi, A.; Leatherbarrow, R. J.; Brauer, A. B. E.; Nievo, M.; Guarna, A. Bioorg. Med. Chem. 2001, 9, 1625.
99. Trabocchi, A.; Occhiato, E. G.; Potenza, D.; Guarna, A. J. Org. Chem. 2002, 67, 7483.
100. Trabocchi, A.; Potenza, D.; Guarna, A. Eur. J. Org. Chem. 2004, 4621.
101. Fisk, J. D.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 5443.