Synthesis of a new spin trap: 2-(Diethoxyphosphoryl)-2-phenyl-3,4- dihydro-2H-pyrrole 1-oxide

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1471-1477

  Karoui, Hakim ^a   Nsanzumuhire, Céline ^a   Le Moigne, François ^a   Tordo, Paul ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 (DIETHOXYPHOSPHORYL) 2 PHENYL 3,4 DIHYDRO 2H PYRROLE 1 OXIDE; FREE RADICAL; PYRROLE DERIVATIVE; SUPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; HALF LIFE TIME; SPIN TRAPPING; SYNTHESIS;

EID: 0033525483     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981875n     Document Type: Article

References (35)

1. Halliwell, B.; Gutteridge, J. M. C. In Free Radicals in Biology and Medicine, 2nd ed.; Oxford: Clarendon Press: 1989; p 422.
2. Korthuis, D. L.; Carden, D. L.; Granger, D. N. In Biological Consequences of Oxidative Stress; Spatz, L., Bloom, D., Eds.; Oxford Press: London, 1992; p 50.
3. (a) Wiseman, H.; Halliwell, B. Biochem. J. 1996, 313, 17.
4. (b) Keyer, K.; Imlay, J. A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13635.
5. Schulz, J. B.; Henshaw, D. R.; Siwek, D.; Jenkins, B. G.; Ferrante, R. J.; Cipolloni, P. B.; Kowall, N. W.; Rosen, B. R.; Beal, M. F. J. Neurochem. 1995, 64, 2239.
6. Degray, J. A.; Mason, R. P. In Electron Spin Resonance; Atherton, N. M., Davies, M. J., Gilbert, B. C., Eds.; Athenæum Press Ltd.: Cambridge, 1994; Vol. 14, p 246.
7. Buettner, G. R. Free Radical Biol. Med. 1987, 3, 259.
8. Buettner, G. R.; Oberley, L. W. Biochim. Biophys. Res. Commun. 1978, 83, 69.
9. (a) Finkelstein, E.; Rosen, G. M.; Rauckman, E. J.; Paxton, J. Mol. Pharmacol. 1979, 16, 676.
10. (b) Finkelstein, E.; Rosen, G. M.; Rauckman, E. J. Mol. Pharmacol. 1982, 21, 262.
11. Finkelstein, E.; Rosen, G. M.; Rauckman, E. J. J. Am. Chem. Soc. 1980, 102, 4994.
12. Finkelstein, E.; Rosen, G. M.; Rauckman, E. J. Arch. Biochem. Biophys. 1980, 200, 1.
13. (e) Buettner, G. R. Free Rad. Res. Commun. 1993, 19, S79.
14. (a) Tordo, P.; Boyer, M.; Santero, O.; Pujol, L. J. Phys. Chem. 1978, 82, 1742.
15. (b) Mercier, A.; Berchadsky, Y.; Badrudin, Y.; Piétri, S.; Tordo, P. Tetrahedron Lett. 1991, 32, 2125.
16. Le Moigne, F.; Mercier, A.; Tordo, P. Tetrahedron Lett. 1991, 32, 3841.
17. Dembrowski, L.; Finet, J. P.; Fréjaville, C.; Le Moigne, F.; Mercier, A.; Pages, P.; Tordo, P. Free Rad. Res. Commun. 1993, 19, S23.
18. (e) Stipa, P.; Finet, J. P.; Le Moigne, F.; Tordo, P. J. Org. Chem. 1993, 58, 4465.
19. (a) Fréjaville, C.; Karoui, H.; Le Moigne, F.; Culcasi, M.; Piétri, S.; Lauricella, R.; Tuccio, B.; Tordo, P. J. Chem. Soc., Chem. Commun. 1994, 1793.
20. (b) Fréjaville, C.; Karoui, H.; Le Moigne, F.; Culcasi, M.; Piétri, S.; Lauricella, R.; Tuccio, B.; Tordo, P. J. Med. Chem. 1995, 38, 258.
21. (a) Zeghdaoui, A.; Tuccio, B.; Finet, J. P.; Cerri, V.; Tordo, P. J. Chem. Soc., Perkin Trans. 2 1995, 12, 2087.
22. (b) Roubaud, V.; Lauricella, R.; Tuccio, B.; Bouteiller, J. C.; Tordo, P. Res. Chem. Intermed. 1996, 22 (4), 405.
23. Roubaud, V.; Mercier, A.; Olive, G.; LeMoigne, F.; Tordo, P. J. Chem. Soc., Perkin Trans. 2 1997, 9, 1827.
24. Janzen, E. G.; Zhang, Y.-K. J. Org. Chem. 1995, 60, 5441.
25. Rockenbauer, A.; Korecz, L.; Hideg, K. J. Chem. Soc., Perkin Trans. 2 1993, 2149.
26. Vaultier, M.; Lambert, P. H.; Carrié, R. Bull. Soc. Chim. Fr. 1986, 1.
27. (a) Makino, K.; Hagiwara, T.; Hagi, A.; Nishi, M.; Murakami, A. Biochem. Biophys. Res. Commun. 1990, 172, 1073.
28. (b) Hanna, P. M.; Chamulitrat, W.; Mason, R. P. Arch. Biochem. Biophys. 1992, 296, 640.
29. Konorev, E. G.; Baker, J. E.; Joseph, J.; Kalyanaraman, B. Free Rad. Biol. Med. 1993, 14, 127.
30. Janzen, E. G.; Zhang, Y-K.; Haire, D. L. J. Am. Chem. Soc. 1994, 116, 3738.
31. Janzen, E. G.; Poyer, J. L.; Schaefer, C. F.; Downs, P. E.; Dubose, C. M. J. Biochem. Biophys. Methods 1995, 30, 239.
32. Thiem, T.; Meyer, B. Org. Magn. Reson. 1978, 11(1), 50.
33. Barbati, Stéphane. Ph.D. Thesis, 1997, University of Aix-Marseille I, France.
34. Duling, D. R.; Motten, A. G.; Mason, R. P. J. Magn. Reson. 1988, 77, 504.
35. Rockenbauer, A.; Korecz, L. Appl. Magn. Reson. 1996, 10, 29.