Convenient synthesis and diversification of dehydroalaninyl phosphinic peptide analogues

Organic Letters

Volumn 3, Issue 5, 2001, Pages 659-660

  Matziari, Magdalini ^a   Georgiadis, Dimitris ^a   Dive, Vincent ^b   Yiotakis, Athanasios ^a  

^a UNIVERSITY OF ATHENS   (Greece)

^b DIF   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; DIPEPTIDE; DRUG DERIVATIVE; GELATINASE A; GELATINASE B; NEUTROPHIL COLLAGENASE; PROTEINASE INHIBITOR;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; SYNTHESIS;

ALANINE; DIPEPTIDES; MATRIX METALLOPROTEINASE 2; MATRIX METALLOPROTEINASE 8; MATRIX METALLOPROTEINASE 9; PROTEASE INHIBITORS;

EID: 0035826345     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0069103     Document Type: Article

References (27)

1. (a) Dive, V.; Cotton, J.; Yiotakis, A.; Michaud, A.; Vassiliou, S.; Jiracek, J.; Vazeaux, G.; Chauvet, M.-T.; Cuniasse, P.; Corvol, P. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4330.
2. (b) Chen, H.; Noble, F.; Coric, P.; Fournie-Zaluski, M. C.; Roques, B. P. Proc. Natl. Acad. Sci. U.S.A. 1998, 96, 12028.
3. (c) Chackalamannil, S.; Chung, S.; Stamford, A. W.; McKittrick, A. B.; Wang, Y.; Tsai, H.; Cleven, R.; Fawzi, A.; Czarniecki, M. Bioorg. Med. Chem. Lett. 1996, 6, 1257.
4. (a) Georgiadis, D.; Vazeux, G.; Llorens-Cortes, C.; Yiotakis, A.; Dive, V. Biochemistry 2000, 39, 1152.
5. (b) Jiracek, J.; Yiotakis, A.; Vincent, B.; Checler, F.; Dive, V. J. Biol. Chem. 1996, 271, 19606.
6. (c) Jiracek, J.; Yiotakis, A.; Vincent, B.; Lecoq, A.; Nicolaou, A.; Checler, F.; Dive, V. J. Biol. Chem. 1995, 270, 21701.
7. Schechter, I.; Berger, A. Biochem. Biophys. Res. Commun. 1967, 27, 157.
8. (a) Boyd, E. A.; Boyd, M. E.; Loh, V. M. Tetrahedron Lett. 1996, 37, 1651.
9. (b) Boyd, E. A.; Corless, M.; James, K.; Regan, A. C. Tetrahedron Lett. 1990, 31, 2933.
10. (c) Thottathil, J. K.; Przybyla, C. A.; Moniot, J. L.; Neubeck, R. Tetrahedron Lett. 1984, 25, 4737.
11. (d) Thottathil, J. K.; Ryono, D. E.; Przybyla, C. A.; Moniot, J. L.; Neubeck, R. Tetrahedron Lett. 1984, 25, 4741.
12. Yiotakis, A.; Vassiliou, S.; Jiracek, J.; Dive, V. J. Org. Chem. 1996, 61, 6601.
13. (a) Amri, H.; Rambaud, M.; Villieras, J. J. Organomet. Chem. 1990, 384, 1.
14. (b) Rabe, J.; Hoffmann, M. R. Angew. Chem., Int. Ed. Engl. 1983, 22, 796.
15. (a) Deane, P. O.; Guthrie-Strachan, J. J.; Kaye, P. T.; Whittaker, R. E. Synth. Commun. 1998, 28, 2601,
16. (b) Bauchat, P.; Le Rouille, E.; Foucaud, A. Bull. Soc. Chim. Fr. 1991, 128, 267.
17. (c) Drewes, S. E.; Slater-Kinghorn, B. J. Synth. Commun. 1986, 16, 603.
18. 6P (431.4): C, 61.25; H, 6.07; N, 3.25. Found: C, 61.59; H, 5.89; N, 3.30.
19. Baylis, E. K.; Campbell, C. D.; Dingwall, J. D. J. Chem. Soc., Perkin Trans. 1 1984, 2845.
20. Schoen, W. R.; Parsons, W. H. Tetrahedron Lett. 1988, 41, 5201.
21. (a) Miller, D. J.; Hammond, S. M.; Anderluzzi, D.; Bugg, T. D. H. J. Chem. Soc., Perkin Trans. 1 1998, 131.
22. (b) Allen, M. C.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood, J. M. J. Med. Chem. 1989, 32, 1652.
23. Makaritis, A. M.Sc. Dissertation, University of Athens, Greece, 2000.
24. (a) Rouvier, E.; Giacomoni, J. C.; Cambon, A. Bull. Soc. Chim. Fr. 1971, 5, 1717.
25. (b) Crossley, M. J.; Fung, Y. M.; Potter, J. J.; Stamford, A. W. J. Chem. Soc., Perkin Trans. 1 1998, 1113.
26. 2. The choice of the (R) configuration was based exclusively on data concerning enzymatic preferences.
27. Vassiliou, S.; Mucha, A.; Cuniasse, P.; Georgiadis, D.; Lucet-Levannier, K.; Beau, F.; Kannan, R.; Murphy, G.; Knauper, V.; Rio, M. C.; Basset, P.; Yiotakis, A.; Dive, V. J. Med. Chem. 1999, 42, 2610.