Nucleophilic Opening of Epoxide by Guanidine. A Route to Potential Substrates or Inhibitors of NO Synthases

Synlett

Volumn 1996, Issue 3, 1996, Pages 275-277

  Gravier Pelletier, Christine ^a   Bourissou, Didier ^a   Le Merrer, Yves ^a   Depezay, Jean Claude ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002624007     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5375     Document Type: Article

References (26)

1. This work was presented at the JCO 95 meeting, Palaiseau (France), september 1995.
2. (a) Bredt, D.S.; Snyder, S.H. Annu. Rev. Biochem. 1994, 63, 175.
3. (b) Feldman, P.L.; Griffith, O.W.; Stuehr, D.J. Chem. Eng. News 1993, 26.
4. (c) Nathan, C.F. FASEB J. 1992, 6, 3051.
5. (a) Kerwin Jr, J.F.; Lancaster Jr, J.R.; Feldman, P.L. J. Med. Chem. 1995, 38, 4343.
6. (b) Korth, H.G.; Sustmann, R.; Thater, C.; Butler, A.R.; Ingold, K.U. J. Biol. Chem. 1994, 269, 17776.
7. (c) Marietta, M.A. J. Biol. Chem. 1993, 268, 12231.
8. "Arginine based inhibitors of induced nitric oxide synthase" Hallinan, E.A.; Tsymbalov, S.; Moore, W.M.; Currie, M.G.; Pitzele, B.S. in abstract from the Fourth International Meeting on the Biology of Nitric Oxide. Sept. 17-21, 1995, Florida.
9. Braun, C.E. J. Am. Chem. Soc. 1933, 55, 1280.
10. (a) Funabashi, Y.; Tsubotani, S.; Koyama, K.; Katayama, N.; Harada, S. Tetrahedron 1993, 49, 13.
11. (b) Kim, K.S.; Qian, L. Tetrahedron Lett. 1993, 34, 7195 and 7677, and references cited therein.
12. (a) Bernatowicz, M.S.; Wu, Y.; Matsueda, G.R. Tetrahedron Lett. 1993, 34, 3389 ; Bernatowicz, M.S.; Wu, Y.; Matsueda, G.R. J. Org. Chem. 1992, 57, 2497, and references cited therein.
13. (a) Bernatowicz, M.S.; Wu, Y.; Matsueda, G.R. Tetrahedron Lett. 1993, 34, 3389 ; Bernatowicz, M.S.; Wu, Y.; Matsueda, G.R. J. Org. Chem. 1992, 57, 2497, and references cited therein.
14. (b) Bergeron, R.J.; McManis, J.S. J. Org. Chem. 1987, 52, 1700.
15. (c) Wojciechowska, H.; Zgoda, W.; Borowski, E. Acta Biochem. Pol. 1982, 29, 197.
16. (d) Wakamiya, T.; Konishi, K.; Chaki, H.; Teshima, T.; Shiba, T. Heterocycles 1981, 15, 999 and references cited therein.
17. Dodd, D.S.; Kozikowski, A.P. Tetrahedron Lett. 1994, 35, 977.
18. Poitout, L.; Le Merrer, Y.; Depezay, J-C. Tetrahedron Lett. 1995, 36, 6887.
19. Tian, Z.; Edwards, P.; Roeske, R.W. Int. J. Peptide Protein Res. 1992, 40, 119.
20. arom), 153.6(C=N), 156.1, 163.6 (C=O).
21. ++1).
22. Jetten, M.; Peters Co A.M.; van Nispen, J.W.F.M.; Ottenheijm, H.C.J. Tetrahedron Lett. 1991, 32, 6025.
23. Bolin, D.R.; Sytwu, I-I.; Humiec, F.; Meienhofer, J. Int. J. Peptide Protein Res. 1989, 33, 353.
24. 3 : C, 67.98 ; H, 6.01 ; N, 6.43. Found : C, 67.89 ; H, 5.91 ; N, 6.51.
25. 6a and 6b are suitably protected guanidino-acids which could be incorporated in conformationally restricted peptidomimetics.
26. The only prior example of epoxide opening by guanidine concerns the cis-benzene trioxide to give a mixture of N,N′-disubstituted guanidines, see : Fritsche-Lang, W.; Wilharm, P.; Hädicke, E.; Fritz, H.; Prinzbach, H. Chem. Ber. 1985, 118, 2044.