Synthesis of 3-amino-4-indolyl-2-piperidones: Tryptophan-derived pseudodipeptides

Heterocycles

Volumn 43, Issue 3, 1996, Pages 513-517

  Rodríguez, Ricardo ^a   Diez, Anna ^a   Rubiralta, Mario ^a   Giralt, Ernest ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343844575     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-7327     Document Type: Article

References (19)

1. D. Mendel, J. Ellman, and P.G. J. Schultz, J. Am. Chem. Soc., 1993, 115, 4359; A. Giannis and T. Kolter, Angew. Chem., Int. Engl.Ed., 1993, 32, 1244, and references cited therein.
2. D. Mendel, J. Ellman, and P.G. J. Schultz, J. Am. Chem. Soc., 1993, 115, 4359; A. Giannis and T. Kolter, Angew. Chem., Int. Engl.Ed., 1993, 32, 1244, and references cited therein.
3. G.R. Marshall, Tetrahedron, 1993, 49, 3547; D.C. Rees, Current Med. Chem., 1994, 1, 145.
4. G.R. Marshall, Tetrahedron, 1993, 49, 3547; D.C. Rees, Current Med. Chem., 1994, 1, 145.
5. I. Lewis and C. Bruns. Tetrahedron, 1994, 50, 7485; W. Kazmierski, W.S. Wire, G.K. Lui, R.J. Knapp, J.E. Shook, T.F. Burks, H.I. Yamamura, and V.J. Hruby, J. Med. Chem., 1988, 31, 2170; Y. Sasaki, W.A. Murphy, M.L. Heiman, V.A. Lance, and D.H. Coy, J. Med. Chem., 1987, 30, 1162.
6. I. Lewis and C. Bruns. Tetrahedron, 1994, 50, 7485; W. Kazmierski, W.S. Wire, G.K. Lui, R.J. Knapp, J.E. Shook, T.F. Burks, H.I. Yamamura, and V.J. Hruby, J. Med. Chem., 1988, 31, 2170; Y. Sasaki, W.A. Murphy, M.L. Heiman, V.A. Lance, and D.H. Coy, J. Med. Chem., 1987, 30, 1162.
7. I. Lewis and C. Bruns. Tetrahedron, 1994, 50, 7485; W. Kazmierski, W.S. Wire, G.K. Lui, R.J. Knapp, J.E. Shook, T.F. Burks, H.I. Yamamura, and V.J. Hruby, J. Med. Chem., 1988, 31, 2170; Y. Sasaki, W.A. Murphy, M.L. Heiman, V.A. Lance, and D.H. Coy, J. Med. Chem., 1987, 30, 1162.
8. K.E. Köver, D. Jiao, S. Fang, and V.J. Hruby, J. Org. Chem., 1994, 59, 991.
9. F. Haviv, C. A. Palabrica, E.N. Bush, G. Diaz, E.S. Johnson, S. Love, and J. Greer, J. Med. Chem., 1989, 32, 2340.
10. A similar variation had been described for phenylalanine rigidified analogues used in a study of renin inhibitors: S.E. Laszlo, B.L. Bush, J.J. Doyle, W.J. Greenlee, D.G. Hangauer, T.A. Halgren, R.J. Lynch, T.W. Schorn, and P.K.S. Siegl, J. Med. Chem., 1992, 35, 833.
11. When the reduction was carried out on the triethyl triester analogue of 7, spontaneous intramolecular lactamization was observed.
12. 8 : C, 67.72; H, 7.14; N, 4.51. Found : C. 67.82; H, 7.13; N, 4.26.
13. When the hydrolysis of triester (10) was assayed directly with 5% aqueous KOH, heating was necessary, and a diastereomeric mixture of the threo and erythro diacids (11) was obtained.
14. ++1).
15. J. Royer, H.-P. Husson, Heterocycles, 1993, 36, 1493.
16. 6 : C, 70.45; H, 5.74; N, 7.25. Found : C, 70.38; H, 5.65; N, 7.15.
17. The diastereomer of compound 12 was detected in the crude reaction mixture by nmr, but we could never isolate it.
18. W.N. Speckamp and H. Hiemstra, Tetrahedron, 1985, 41, 4367.
19. 5: C, 72.18; H, 6.24; N. 7.43. Found: C, 72.21; H, 5.98; N, 7.21.