New routes to conformationally restricted peptide building blocks: A convenient preparation of bicyclic piperazinone derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 3, 1996, Pages 315-318

  Fobian, Yvette M ^a   Andre D'Avignon D ^a   Moeller, Kevin D ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERAZINE DERIVATIVE;

ARTICLE; COMPUTER SIMULATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PEPTIDE SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030040826     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00019-4     Document Type: Article

References (39)

1. For recent reviews describing the syntheses of conformationally restricted peptide mimetics see: a. Toniolo, C. Int. J. Peptide Protein Res. 1990, 35, 287,
2. b. Hölzemann, G. Kontakte (Darmstadt) 1991, 1, 3,
3. c. 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.; Saraby, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039, and
4. d. Giannis, A.; Koller, T. Angew. Chem. Int. Ed. Eng. 1993, 32, 1244.
5. For selected examples of related lactam based peptide mimetics see: a. Wolf, J. P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164,
6. b. Freidinger, R. M.; Perlow, D. S.; Veber, D. F. J. Org. Chem. 1982, 47, 104,
7. c. Freidinger, R. M. J. Org. Chem. 1985, 50, 3631,
8. d. Zydowsky, T. M.; Dellaria, Jr., J. F.; Nellans, H. N. J. Org. Chem. 1988, 53, 5607,
9. e. Kempf, D. J.; Condon, S. L. J. Org. Chem. 1990, 55 1390,
10. f. Kemp, D. S.; McNamara, P. E. J. Org. Chem. 1985, 50, 5834,
11. g. Nagai, U; Sato, K. Tetrahedron Lett. 1985, 26, 647,
12. h. Hinds, M. G.; Richards, N. G. J.; Robinson, J. A. J. Chem. Soc., Chem. Commun. 1988, 1447,
13. i. Paul, P. K. C.; Burney, P. A.; Campbell, M. M.; Osguthorpe, D. J. Bioorg. Med. Chem. Lett. 1992, 2, 141,
14. j. Ward, P.; Ewan, G. B.; Jordon, C. C.; Ireland, S. J.; Hagan, R. M.; Brown, J. R. J. Med. Chem. 1990, 33, 1848,
15. k. Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914,
16. l. Flynn, G. A.; Burkholder, T. P.; Huber, E. W.; Bey, P. Bioorg. Med. Chem. Lett. 1991, 1, 309, and
17. m. Burkholder, T. P.; Huber, E. W.; Flynn, G. A. Bioorg. Med. Chem. Lett. 1993, 3, 231.
18. a. Moeller, K. D.; Rothfus, S. L.; Wong, P. L. Tetrahedron 1991, 47, 583,
19. b. Wong, P. L.; Moeller, K. D. J. Am. Chem. Soc. 1993, 115, 11434,
20. c. Moeller, K. D.; Hanau, C. E.; d'Avignon, D. A. Tetrahedron Lett. 1994, 35, 835,
21. d. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989,
22. e. Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 909, and
23. f. Li, W.; Hanau, C. E.; d'Avignon, D. A.; Moeller, K. D. J. Org. Chem. 1995, in press.
24. Unpublished results with Mr. Yungsong Tong.
25. For a convenient approach to cis-peptide bond mimetics of this type see: Gramberg, D.; Robinson, J. A. Tetrahedron Lett. 1994, 35, 861
26. and Dumas, J. -P.; Germanas, J. P. Tetrahedron Lett. 1994, 35, 1493.
27. Regoli, D.; Escher, E.; Mizrahi, J. Pharmacology 1984, 28, 301.
28. Private communication from Nikoforovich, G. V. and Marshall, G. R.
29. For the use of piperazinone rings as conformational constriants for peptides see: a. DiMaio, J.; Belleau, B.; J. Chem. Soc. Perkin Trans. 1 1989, 1687,
30. b. Kolter, T.; Klein, A.; Giannis, A. Angew. Chem. Int. Ed. Engl. 1992, 31, 1391,
31. c. Bravo, A.; Gomez-Monterrey, I.; Gonzalez-Muniz, R.; Garcia-Lopez, M. T. J. Chem. Soc. Perkin Trans. 1 1991, 3117,
32. d. Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985, and
33. e. Schanen, V.; Riche, C.; Chiaroni, A.; Quiroion, J. -C.; Husson, H. -P. Tetrahedron Lett. 1994, 35, 2533.
34. For reviews of anodic amide oxidations see a. Shono, T. Tetrahedron 1984, 40, 811,
35. b. Shono, T.; Matsumura, Y.; Tsubata, K. In Organic Synthesis vol. 63, Saucy, G. Ed.; Organic Synthesis Inc., 1984, pg. 206 and references therein, and
36. c. Shono, T. In Topics in Current Chemistry vol. 148, Steckhan, E. Ed., Springer-Verlag, Berlin Heidelberg, New York, 1988, pg 131.
37. For a directly analogous route to the carbomethoxy protected 5-(2′-methy-1-propenyl)proline derivative see: Thaning, M.; Wistrand, L. -G. Acta Chemica Scandanavica 1992, 46, 194.
38. Carpino, L. A.; Mansour, E. M. E.; Sadat-Aalaee, D. J. Org. Chem. 1991, 56, 2611.
39. d'Avingnon, D. A.; Hanau, C. E.; Fobian, Y. M.; Moeller, K. D. Coordination Chem. 1994, 32, 135.