Controlled oxidation of thiols to disulfides by diazenecarboxamides

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 23, 1998, Pages 3917-3919

  Košmrlj, Janez ^a   Kočevar, Marijan ^a   Polanc, Slovenko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748730944     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808381i     Document Type: Article

References (30)

1. For example, see: (a) B. Schmidt, S. Lindman, W. Tong, G. Lindeberg, A. Gogoll, Z. Lai, M. Thörnwall, B. Synnergren, A. Nilsson, C. J. Welch, M. Sohtell, C. Westerlund, F. Nyberg, A. Karlén and A. Hallberg, J. Med. Chem., 1997, 40, 903;
2. (b) K. W. Li, J. Wu, W. Xing and J. A. Simon, J. Am. Chem. Soc., 1996, 118, 7237;
3. (c) Glutathione: Metabolism and Physiological Functions, ed. J. Viňa, CRC Press, Boca Raton, 1990;
4. (d) Glutathione: Chemical, Biochemical, and Medical Aspects, eds. D. Dolphin, R. Poulson and O. Avramović, Wiley-Interscience, New York, 1989, Part A and Part B.
5. B. D. Palmer, G. W. Rewcastle, A. M. Thompson, M. Boyd, H. D. H. Showalter, A. D. Sercel, D. W. Fry, A. J. Kraker and W. A. Denny, J. Med. Chem., 1995, 38, 58, and references therein.
6. For comprehensive discussion on the oxidative stress chemotherapeutic strategy, see: R. H. Schirmer, J. G. Müller and R. L. Krauth-Siegel, Angew. Chem., Int. Ed. Engl., 1995, 34, 141.
7. (a) E. M. Kosower in ref. 1(d), Part A, pp. 103-146;
8. (b) N. S. Kosower and E. M. Kosower in ref. 1(d), Part B, pp. 319-356;
9. (c) E. M. Kosower and N. S. Kosower, Nature, 1969, 224, 117.
10. (a) D. J. Jebaratnam, S. Kugabalasooriar, H. Chen and D. P. Arya, Tetrahedron Lett., 1995, 36, 3123;
11. (b) E. M. Kosower and H. Kanety-Londner, J. Am. Chem. Soc., 1976, 98, 3001;
12. (c) E. M. Kosower and T. Miyadera, J. Med. Chem., 1972, 15, 307;
13. (d) E. M. Kosower, Acc. Chem. Res., 1971, 4, 193.
14. (a) M. Kočevar, P. Sušin and S. Polanc, Synthesis, 1993, 773;
15. (b) M. Kočevar, P. Mihorko and S. Polanc, Synlett, 1995, 241;
16. (c) B. Štefane, M. Kočevar and S. Polanc, J. Org. Chem., 1997, 62, 7165.
17. M. Kočevar, P. Mihorko and S. Polanc, J. Org. Chem., 1995, 60, 1466.
18. J. Košmrlj, M. Kočevar and S. Polanc, Synlett, 1996, 652.
19. Thallium and its compounds are toxic and must be handled with care. See, I. E. Markó and C. W. Leung, J. Am. Chem. Soc., 1994, 116, 371.
20. J. Heinze, Angew. Chem., Int. Ed. Engl., 1984, 23, 831.
21. -1; counter electrode: Pt wire; reference Ag/AgCl (sat. aq. KCl); temperature: 20°C.
22. For example, see: (a) H. F. Gilbert, Comprehensive Biological Catalysts: A Mechanistic Reference, ed. M. Sinnott, Academic, San Diego, 1998, vol. 1, pp. 609-625;
23. (b) A. Meister in ref. 1(d). Part A, pp. 1-48 and pp. 367-474.
24. (a) J. M. Domagala, J. P. Bader, R. D. Gogliotti, J. P. Sanchez, M. A. Stier, Y. Song, J. V. N. Vara Prasad, P. J. Tummino, J. Scholten, P. Harvey, T. Holler, S. Gracheck, D. Hupe, W. G. Rice and R. Schultz, Bioorg. Med. Chem., 1997, 5, 569;
25. (b) N. B. McDonnell, R. N. De Guzman, W. G. Rice, J. A. Turpin and M. F. Summers, J. Med Chem., 1997, 40, 1969;
26. (c) W. G. Rice, J. A. Turpin, C. A. Schaeffer, L. Graham, D. Clanton, R. W. Buckheit Jr., D. Zaharevitz, M. F. Summers, A. Wallqvist and D. G. Covell, J. Med. Chem., 1996, 39, 3606;
27. (d) J. A. Loo, T. P. Holler, J. Sanchez, R. Gogliotti, L. Maloney and M. D. Reily, J. Med. Chem., 1996, 39, 4313;
28. (e) W. G. Rice, J. G. Supko, L. Malspeis, R. W. Buckheit Jr., D. Clanton, M. Bu, L. Graham, C. A. Schaeffer, J. A. Turpin, J. Domagala, R. Gogliotti, J. P. Bader, S. M. Halliday, L. Coren, R. C. Sowder II, L. O. Arthur and L. E. Henderson, Science, 1995, 270, 1194.
29. For recent references, see: (a) M. Zhene, F. Aslund and G. Storz, Science, 1998, 279, 1718;
30. (b) B. Demple, Science, 1998, 279, 1655.