Efficient synthesis of conformationally constrained peptidomimetics containing 2-oxopiperazines

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 1016-1022

  Pohlmann, Adriana ^a,b   Schanen, Vincent ^a   Guillaume, Dominique ^a   Quirion, Jean Charles ^a   Husson, Henri Philippe ^a  

^a FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

2 PIPERAZINONE DERIVATIVE; OLIGOPEPTIDE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030936052     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961398d     Document Type: Article

References (23)

1. Abbreviations used: DCC, dicyclohexylcarbodiimide; DMF, dimethylformamide; HMPA, hexamethylphosphoramide; IBCF, isobutyl chloroformate; NMM, N-methylmorpholine; THF, tetrahydrofuran; TBDMSCl, tert-butyldimethylsilyl chloride.
2. (a) Hruby, V.; Al-Obedi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249.
3. (b) Fesik, S. W. J. Med. Chem. 1991, 34, 2937.
4. (c) Marshall, G. R. Tetrahedron 1993, 49, 3547.
5. Freidinger, R. M.; Veber, D. F.; Perlow, D. S.; Brooke, J. R.; Saperstein, R. Science 1980, 210, 656.
6. Recent reviews: Toniolo, C. Int. J. Peptide Protein Res. 1990, 35, 287. Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 1. Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
7. Recent reviews: Toniolo, C. Int. J. Peptide Protein Res. 1990, 35, 287. Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 1. Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
8. Recent reviews: Toniolo, C. Int. J. Peptide Protein Res. 1990, 35, 287. Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 1. Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
9. Piercy, M. F.; Moon, M. W.; Blinn, J. R.; Dobry-Scheur, P. J. K. Brain Res. 1986, 74, 385.
10. DiMaio, J.; Belleau, B. J. Chem. Soc., Perkin Trans. 1 1989, 1687.
11. Kojima, Y.; Yamashita, T.; Washizawa, M.; Ohsuka, A. Makromol. Chem., Rapid Commun. 1989, 10, 1989.
12. Yamashita, T.; Kojima, Y.; Hirotsu, K.; Ohsuka, A. Int. J. Peptide Protein Res. 1989, 33, 110.
13. Fobian, Y. M.; d'Avignon, D. A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315.
14. (a) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533.
15. (b) Schanen, V.; Cherrier, M. P.; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833.
16. Micouin, L.; Jullian, V.; Quirion, J.-C.; Husson, H.-P. Tetrahedron: Asymmetry 1996, 7, 2839.
17. Micouin, L.; Varea, T.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2529.
18. Sandrin, E.; Boissonnas, R. A. Helv. Chim. Acta 1963, 46, 1637.
19. Guillaume, D.; Brum-Bousquet, M.; Aitken, D. J.; Husson, H.-P. Bull. Soc. Chim. Fr. 1994, 131, 391.
20. Gante, J.; Neunhoeffer, H.; Schmidt, A. J. Org. Chem. 1994, 59, 6487.
21. Lindner, E.; von Au, G.; Eberle, H.-J. Chem. Ber. 1981, 114, 810.
22. Hamada, Y.; Shibata, M.; Sugiura, T.; Kato, S.; Shioiri, T. J. Org. Chem. 1987, 52, 1252.
23. Chiaroni, A.; Riche, C.; Pohlmann, A.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P. Acta Crystallogr. To be published.