A novel camphor-derived selenamide that acts as a glutathione peroxidase mimetic

Journal of the American Chemical Society

Volumn 119, Issue 9, 1997, Pages 2079-2083

  Back, Thomas G ^a   Dyck, Brian P ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; GLUTATHIONE PEROXIDASE; ORGANOSELENIUM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENZYME ACTIVITY; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030936613     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963602k     Document Type: Article

References (37)

1. Free Radicals in Biology; Pryor, W. A., Ed.; Academic Press: New York, 1976; Vols. 1-3.
2. (a) Hoekstra, W. G. In Trace Element Metabolism in Animals-2; Hoekstra, W. G., Suttie, J. W., Ganther, H. E., Mertz, W., Eds.; University Park Press: Baltimore, 1974.
3. (b) Shamberger, R. J. Biochemistry of Selenium; Plenum Press: New York, 1983.
4. (c) Selenium in Biology and Human Health; Burk, R. F., Ed.; Springer-Verlag: New York, 1994.
5. (d) Tappel, A. L. Curr. Top. Cell Regul. 1984, 24, 87.
6. (e) Hohe, L. Curr. Top. Cell Regul. 1985, 27, 473.
7. Epp, O.; Ladenstein, R.; Wendel, A. Eur. J. Biochem. 1983, 133, 51.
8. (a) Ganther, H. E. Chem. Scripta 1975, 8a, 79.
9. (b) Ganther, H. E.; Kraus, R. J. In Methods in Enzymology; Colowick, S. P., Kaplan, N. O., Eds.; Academic Press: New York, 1984; Vol. 107, pp 593-602.
10. (a) Müller, A.; Cadenas, E.; Graf, P.; Sies, H. Biochem. Pharmacol 1984, 33, 3235.
11. (b) Wendel, A.; Fausel, M.; Safayhi, H.; Tiegs, G.; Otter, R. Biochem. Pharmacol. 1984, 33, 3241.
12. (c) Parnham, M. J.; Kindt, S. Biochem. Pharmacol. 1984, 33, 3247.
13. (d) Müller, A.; Gabriel, H.; Sies, H. Biochem. Pharmacol. 1985, 34, 1185.
14. (e) Safayhi, H.; Tiegs, G.; Wendel, A. Biochem. Pharmacol 1985, 34, 2691.
15. (f) Wendel, A.; Tiegs, G. Biochem. Pharmacol. 1986, 35, 2115.
16. For lead references, see: (a) Fong, M. C.; Schiesser, C. H. Tetrahedron Lett. 1995, 36, 7329. (b) Jacquemin, P. V.; Christiaens, L. E.; Renson, M. J.; Evers, M. J.; Dereu, N. Tetrahedron Lett. 1992, 33, 3863. (c) Galet, V.; Dernier, J.-L.; Hénichart, J.-P.; Lesieur, D.; Abadie, C.; Röchelte, L.; Lindenbaum, A.; Chalas, J.; Renaud de la Faverie, J.-F.; Pfeiffer, B.; Renard, P. J. Med. Chem. 1994, 37, 2903.
17. For lead references, see: (a) Fong, M. C.; Schiesser, C. H. Tetrahedron Lett. 1995, 36, 7329. (b) Jacquemin, P. V.; Christiaens, L. E.; Renson, M. J.; Evers, M. J.; Dereu, N. Tetrahedron Lett. 1992, 33, 3863. (c) Galet, V.; Dernier, J.-L.; Hénichart, J.-P.; Lesieur, D.; Abadie, C.; Röchelte, L.; Lindenbaum, A.; Chalas, J.; Renaud de la Faverie, J.-F.; Pfeiffer, B.; Renard, P. J. Med. Chem. 1994, 37, 2903.
18. For lead references, see: (a) Fong, M. C.; Schiesser, C. H. Tetrahedron Lett. 1995, 36, 7329. (b) Jacquemin, P. V.; Christiaens, L. E.; Renson, M. J.; Evers, M. J.; Dereu, N. Tetrahedron Lett. 1992, 33, 3863. (c) Galet, V.; Dernier, J.-L.; Hénichart, J.-P.; Lesieur, D.; Abadie, C.; Röchelte, L.; Lindenbaum, A.; Chalas, J.; Renaud de la Faverie, J.-F.; Pfeiffer, B.; Renard, P. J. Med. Chem. 1994, 37, 2903.
19. Reich, H. J.; Jasperse, C. P. J. Am. Chem. Soc. 1987, 709, 5549.
20. (a) Wilson, S. R.; Zucker, P. A.; Huang, R.-R. C.; Spector, A. J. Am. Chem. Soc. 1989, 111, 5936.
21. (b) Iwaoka, M.; Tomoda, S. J. Am. Chem. Soc. 1994, 116, 2557.
22. Engman, L.; Stern, D.; Cotgreave, I. A.; Andersson, C. M. J. Am. Chem. Soc. 1992, 114, 9737.
23. (a) Engman, L.; Stern, D.; Pelcman, M.; Andersson, C. M. J. Org. Chem. 1994, 59, 1973.
24. (b) Vessman, K.; Ekström, M.; Berglund, M.; Andersson, C. M. J. Org. Chem. 1995, 60, 4461.
25. Engman, L.; Andersson, C.; Morgenstern, R.; Cotgreave, I. A.; Andersson, C. M.; Hallberg, A. Tetrahedron 1994, 50, 2929.
26. Detty, M. R.; Friedman, A. E.; Oseroff, A. R. J. Org. Chem. 1994, 59, 8245.
27. (a) Wu, Z.-R; Hilvert, D. J. Am. Chem. Soc. 1990, 112, 5647.
28. (b) Wu, Z.-P.; Hilvert, D. J. Am. Chem. Soc. 1989, 111, 4513.
29. Fischer, H.; Dereu, N. Bull. Soc. Chim. Belg. 1987, 96, 757.
30. Haenen, G. R. M. M.; De Rooij, B. M.; Vermeulen, N. P. E.; Bast, A. Mol. Pharmacol. 1990, 37, 412.
31. (a) Kice, J. L.; Lee, T. W. S. J. Am. Chem. Soc. 1978, 100, 5094.
32. (b) Kice, J. L.; Purkiss, D. W. J. Org. Chem. 1987, 52, 3448.
33. Glass, R. S.; Farooqui, F.; Sabahi, M.; Ehler, K. W. J. Org. Chem. 1989, 54, 1092.
34. (a) Back, T. G.; Dyck, B. P. J. Chem. Soc., Chem. Commun. 1996, 2567.
35. (b) Back, T. G.; Dyck, B. P.; Parvez, M. J. Org. Chem. 1995, 60. 703.
36. The formation of the diselenide 5 from selenol 9 would presumably proceed through the same selenenic acid intermediate 10 (or a related species such as its anhydride) that produces the selenenyl sulfide 8. In the presence of a relatively high concentration of thiol and a low concentration of selenol, the direct formation of 8 instead of 5 from 10 is not surprising.
37. Chivers, T.; Doxsee, D. D.; Parvez, M. Inorg. Chem. 1993, 32, 2238.