Novel bicyclic lactams as XaaPro type VI β turn mimics: Design, synthesis, and evaluation

Journal of Organic Chemistry

Volumn 61, Issue 9, 1996, Pages 3138-3144

  Kim, Kyonghee ^a   Dumas, Jean Philippe ^a   Germanas, Juris P ^a  

^a University of Houston ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZIDINE DERIVATIVE; LACTAM DERIVATIVE; PROLINE DERIVATIVE;

ARTICLE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE;

EID: 0029980149     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960012w     Document Type: Article

References (49)

1. Stewart, D. E.; Sarkar, A.; Wampler, J. E. J. Mol. Biol. 1990, 214, 253-260.
2. (a) Eberhardt, E. S.; Loh, S. N.; Raines, R. T. Tetrahedron Lett. 1993, 34, 3055-3056.
3. (b) Kofron, J. L.; Kuzmic, P.; Kishore, V.; Bonilla, E.; Rich, D. H. Biochemistry 1991, 30, 6127-6134.
4. Eberhardt, E. S.; Loh, S. N.; Hinck, A. P.; Raines, R. T. J. Am. Chem. Soc. 1992, 114, 5437-5439.
5. Schmid, F. X.; Mayr, L. M.; Mucke, M.; Schonbrunner, E. R. Adv. Protein Chem. 1993, 44, 25-66.
6. Laikopoulou-Kyriakides, M.; Galardy, R. E. Biochemistry 1979, 18, 1952-1957.
7. (a) Shai, Y.; Bach, D.; Yanovsky, A. J. Biol. Chem. 1990, 265, 20202-20209.
8. (b) Williams, K. A.; Deber, C. M. Biochemistry 1991, 30, 8919-8923.
9. (c) Suchnya, T. M.; Xu, L. X.; Gao, F.; Fourtner, C. R.; Nicholson, B. J. Nature 1993, 365, 847-849.
10. (d) Wellner, M.; Monden, I.; Mueckler, M. M.; Keller, K. Eur. J. Biochem. 1995, 227, 454-458.
11. Yaron, A.; Naider, F. Crit. Rev. Biochem. Mol. Biol. 1993, 28, 31-81.
12. Schreiber, S. L. Science 1991, 251, 283-287. Fischer, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1415-1436.
13. Schreiber, S. L. Science 1991, 251, 283-287. Fischer, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1415-1436.
14. Fruman, D. A.; Burakoff, S. J.; Bierer, B. E. FASEB J. 1994, 8, 391-400.
15. (a) Franke, E. K.; Yuan, H.; Luban, J. Nature 1994, 372, 359-362.
16. (b) Thali, M.; Bukovsky, A.; Kondo, E.; Rosenwirth, B.; Walsh, C. T.; Sodroski, J.; Gottlinger, H. G. Ibid. 1994, 372, 363-365.
17. Richardson, J. S.; Richardson, D. C. In Prediction of Protein Structure and the Principles of Protein Conformation; Fasman, G. D., Ed.; Plenum Press: New York; 1989, pp 48-53.
18. (a) Yao, J.; Fehrer, V. A.; Espejo, B. F.; Reymond, M. T.; Wright, P. E.; Dyson, H. J. J. Mol. Biol. 1994, 243, 736-753.
19. (b) Yao, J.; Bruschweiler, R.; Dyson, H. J.; Wright, P. E. J. Am. Chem. Soc. 1994, 116, 12051-12052.
20. (a) Kallen, J.; Wlakinshaw, M. D. FEBS Lett. 1992, 300, 286.
21. (b) Orozco, M.; Tirado-Rives, J.; Jorgensen, W. L. Biochemistry 1993, 32, 12864-12874.
22. (c) Fischer, S.; Michnick, S.; Karplus, M. Ibid. 1993, 32, 13830-13837.
23. (a) Freidinger, R. M.; Perlow, D. S.; Randall, W. C.; Saperstein, R.; Arison, B. H.; Veber, D. F. Int. J. Pept. Protein Res. 1984, 23, 142-150.
24. (b) Eggleston, D. S.; Baures, P. W.; Peishoff, C. E.; Kopple, K. D. J. Am. Chem. Soc. 1991, 113, 4410-4416.
25. (a) Hruby, V. J. Life Sci. 1982, 31, 189-199.
26. (b) Toniolo, C. Int. J. Pept. Protein Res. 1990, 35, 287-300.
27. (c) Rizo, J.; Gierasch, L. M. Ann. Rev. Biochem. 1992, 61, 397-418.
28. (a) Ball, J. B.; Alewood, P. F. J. Mol. Recognit. 1990, 3, 55-64.
29. (b) Kemp, D. S. Trends Biol. Sci. 1990, 8, 249-255.
30. (c) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720.
31. Portions of this work were described in a previous note. See: Dumas, J.-P.; Germanas, J. P. Tetrahedron Lett. 1994, 35, 1493-1496. The synthesis of a structurally similar compound was simultaneously reported by another group; see Gramberg, D.; Robinson, J. A. Tetrahedron Lett. 1994, 35, 861-864.
32. Portions of this work were described in a previous note. See: Dumas, J.-P.; Germanas, J. P. Tetrahedron Lett. 1994, 35, 1493-1496. The synthesis of a structurally similar compound was simultaneously reported by another group; see Gramberg, D.; Robinson, J. A. Tetrahedron Lett. 1994, 35, 861-864.
33. Germanas, J. P., in preparation.
34. Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390-5398.
35. Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984, 53-60.
36. Aube, J.; Milligan, G. L. J. Am. Chem. Soc. 1991, 113, 8966-8967.
37. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Sterochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; p 729.
38. Meguro, H.; Konno, T.; Tuzimura, K. Tetrahedron Lett. 1975, 1309-1312.
39. f lactam crystallized from ethyl acetate as flat plates as the monohydrate. The space group was determined to be Pbca. Crystallographic data, including the fractional atomic coordinates, together with distances and angles of covalent bonds involving non-hydrogen atoms have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
40. The Chemistry of Amides; Zabicky, J., Ed.; Wiley: London, 1970.
41. For strained bicyclic amides, see: (a) Somayaji, V.; Brown, B. S. J. Org. Chem. 1986, 51, 2676-2686. (b) Wang, Q.-P.; Bennet, A. J.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 5757-5765. For strained monocyclic lactams, see: Dunitz, J. D.; Winkler, F. K. Acta Crystallogr. 1975, B31, 251-263. (c) For strained acyclic amides, see: Yamada, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1113-1115 and references therein. (d) For amides in which the nitrogen atom is incorporated into an aziridine ring, see: Shao, H.; Jiang, X.; Gantzel, P.; Goodman, M. Chem. Biol. 1994, 1, 231-234.
42. For strained bicyclic amides, see: (a) Somayaji, V.; Brown, B. S. J. Org. Chem. 1986, 51, 2676-2686. (b) Wang, Q.-P.; Bennet, A. J.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 5757-5765. For strained monocyclic lactams, see: Dunitz, J. D.; Winkler, F. K. Acta Crystallogr. 1975, B31, 251-263. (c) For strained acyclic amides, see: Yamada, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1113-1115 and references therein. (d) For amides in which the nitrogen atom is incorporated into an aziridine ring, see: Shao, H.; Jiang, X.; Gantzel, P.; Goodman, M. Chem. Biol. 1994, 1, 231-234.
43. For strained bicyclic amides, see: (a) Somayaji, V.; Brown, B. S. J. Org. Chem. 1986, 51, 2676-2686. (b) Wang, Q.-P.; Bennet, A. J.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 5757-5765. For strained monocyclic lactams, see: Dunitz, J. D.; Winkler, F. K. Acta Crystallogr. 1975, B31, 251-263. (c) For strained acyclic amides, see: Yamada, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1113-1115 and references therein. (d) For amides in which the nitrogen atom is incorporated into an aziridine ring, see: Shao, H.; Jiang, X.; Gantzel, P.; Goodman, M. Chem. Biol. 1994, 1, 231-234.
44. For strained bicyclic amides, see: (a) Somayaji, V.; Brown, B. S. J. Org. Chem. 1986, 51, 2676-2686. (b) Wang, Q.-P.; Bennet, A. J.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 5757-5765. For strained monocyclic lactams, see: Dunitz, J. D.; Winkler, F. K. Acta Crystallogr. 1975, B31, 251-263. (c) For strained acyclic amides, see: Yamada, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1113-1115 and references therein. (d) For amides in which the nitrogen atom is incorporated into an aziridine ring, see: Shao, H.; Jiang, X.; Gantzel, P.; Goodman, M. Chem. Biol. 1994, 1, 231-234.
45. For strained bicyclic amides, see: (a) Somayaji, V.; Brown, B. S. J. Org. Chem. 1986, 51, 2676-2686. (b) Wang, Q.-P.; Bennet, A. J.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 5757-5765. For strained monocyclic lactams, see: Dunitz, J. D.; Winkler, F. K. Acta Crystallogr. 1975, B31, 251-263. (c) For strained acyclic amides, see: Yamada, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1113-1115 and references therein. (d) For amides in which the nitrogen atom is incorporated into an aziridine ring, see: Shao, H.; Jiang, X.; Gantzel, P.; Goodman, M. Chem. Biol. 1994, 1, 231-234.
46. Winkler, F. K.; Dunitz, J. D. Acta Crystallogr. 1975, B31, 268-270.
47. Winkler, F. K.; Dunitz, J. D. J. Mol. Biol. 1971, 59, 169-182.
48. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Sterochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; p 727.
49. Vedejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612-11613.