Synthesis, characterization, and antioxidant activity of some ebselen analogues

Chemistry - A European Journal

Volumn 13, Issue 16, 2007, Pages 4594-4601

  Bhabak, Krishna P ^a   Mugesh, Govindasamy ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Antioxidant activity; Ebselen; Enzymes; Selenium; Selenoenzymes

Indexed keywords

AROMATIC THIOLS; EBSELEN; GLUTATHIONE PEROXIDASE; ORGANOSELENIUM DRUG;

CATALYSTS; DENSITY FUNCTIONAL THEORY; DERIVATIVES; HYDROGEN PEROXIDE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

DRUG PRODUCTS;

ANTIOXIDANT; BENZYL DERIVATIVE; CUMINYL HYDROPEROXIDE; EBSELEN; GLUTATHIONE PEROXIDASE; HYDROGEN PEROXIDE; ORGANOSELENIUM DERIVATIVE; PYRROLE DERIVATIVE; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTIOXIDANTS; AZOLES; BENZYL COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; GLUTATHIONE PEROXIDASE; HYDROGEN PEROXIDE; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOSELENIUM COMPOUNDS; TERT-BUTYLHYDROPEROXIDE;

EID: 34250314399     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601584     Document Type: Article

References (53)

1. T. C. Stadtman, Annu. Rev. Biochem. 1996, 65, 83-100.
2. a) L. Flohe, E. A. Günzler, H. H. Schock, FEBS Lett. 1973, 32, 132-134;
3. b) J. T. Rotruck, A. L. Pope, H. E. Ganther, A. B. Swanson, D. G. Hafeman, W. G. Hoekstra, Science 1973, 179, 588-590.
4. a) J. R. Arthur, F. Nicol, G. J. Beckett, Biochem. J. 1990, 272, 537-540;
5. b) M. J. Berry, L. Banu, P. R. Larsen, Nature, 1991, 349, 438-440;
6. c) J. Köhrle, Methods Enzymol. 2002, 347, 125-167;
7. d) A. C. Bianco, D. Salvatore, B. Gereben, M. J. Berry, P. R. Larsen, Endocr. Rev. 2002, 23, 38-89.
8. a) S.-R. Lee, J.-R. Kim, K.-S. Kwon, H. W. Yoon, R. L. Leveine, A. Ginsburg, S. G. Rhee, J. Biol. Chem. 1999, 274, 4722-4734;
9. b) C. H. Williams, Jr, L. D. Arscott, S. Müller, B. W. Lennon, M. L. Ludwig, P.-F. Wang, D. M. Veine, K. Becker, R. H. Schirmer, Eur. J. Biochem. 2000, 267, 6110-6117.
10. a) "Oxidative Stress: Introductory Remarks" H. Sies, in Oxidative Stress (Ed.: H. Sies) Academic Press, London, 1985, pp. 1-8;
11. b) H. Sies, Angew. Chem. 1986, 98, 1061-1075;
12. Angew. Chem. Int. Ed. Engl. 1986, 25, 1058-1071.
13. a) H. Nakamura, K. Nakamura, J. Yodoi, Ann. Rev. Immunol. 1997, 15, 351-369;
14. b) E. S. Arnér, A. Holmgren, Eur. J. Biochem. 2000, 267, 6102-6109.
15. a) A. Müller, E. Cadenas, P. Graf, H. Sies, Biochem. Pharmacol. 1984, 33, 3235-3239;
16. b) A. Wendel, M. Fausel, H. Safayhi, G. Tiegs, R. Otter, Biochem. Pharmacol. 1984, 33, 3241-3245;
17. c) G. Mugesh, H. B. Singh, Chem. Soc. Rev. 2000, 29, 347-357;
18. d) G. Mugesh, W.-W. du Mont, H. Sies, Chem. Rev. 2001, 101, 2125-2179.
19. V. Galet, J.-L. Bernier, J.-P. Hénichart, D. Lesieur, C. Abadie, L. Rochette, A. Lindenbaum, J. Chalas, J.-F. Renaud de la Faverie, B. Pfeiffer, P. Renard, J. Med. Chem. 1994, 37, 2903-2911.
20. T. G. Back, B. P. Dyck, J. Am. Chem. Soc. 1997, 119, 2079-2083.
21. K. Vessman, M. Ekstsröm, M. Berglund, C. M. Andersson, L. Engman, J. Org. Chem. 1995, 60, 4461-4467.
22. a) S. R. Wilson, P. A. Zucker, R.-R. C. Huang, A. Spector, J. Am. Chem. Soc. 1989, 111, 5936-5939;
23. b) M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 1994, 116, 2557-2561;
24. c) T. Wirth, Molecules, 1998, 3, 164-166;
25. d) M. L. Jauslin, T. Wirth, T. Meier, F. Schoumacher, Hum. Mol. Genet. 2002, 11, 3055-3063;
26. e) G. Mugesh, A. Panda, H. B. Singh, N. S. Punekar, R. J. Butcher, J. Am. Chem. Soc. 2001, 123, 839-850;
27. f) Y. Sun, Y. Mu, S. Ma, P. Gong, G. Yan, J. Liu, J. Shen, G. Luo, Biochim. Biophys. Acta 2005, 1743, 199-204.
28. a) T. G. Back, Z. Moussa, J. Am. Chem. Soc. 2002, 124, 12104-12105;
29. b) T. G. Back, Z. Moussa, M. Parvez, Angew. Chem. 2004, 116, 1288-1290;
30. Angew. Chem. Int. Ed. 2004, 43, 1268-1270.
31. P.P. Phadnis, G. Mugesh, Org. Biomol. Chem. 2005, 3, 2476-2481.
32. S. S. Zade, H. B. Singh, R. J. Butcher, Angew. Chem. 2004, 116, 4613-4615;
33. Angew. Chem. Int. Ed. 2004, 43, 4513-4515.
34. B. K. Sarma, G. Mugesh, J. Am. Chem. Soc. 2005, 127, 11477-11485.
35. H. Shi, S. Liu, M. Miyake, K. J. Liu, Chem. Res. Toxicol. 2006, 19, 655-660, and references therein.
36. R. Cantineau, G. Tihange, A. Plenevaux, L. Christiaens, M. Guillaume, A. Welter, N. Dereu, J. Labelled Compd. Radiopharm. 1986, 23, 59-65.
37. a) J. K. Pearson, R. J. Boyd, J. Phys. Chem. A. 2006, 110, 8979-8985;
38. b) S. Benkova, J. Kóña, G. Gann, W. M. F. Fabian, Int. J. Quantum Chem. 2002, 90, 555-565;
39. c) S. Bachrach, D.W. Demoin, M. Luk, J. V. Miller, Jr., J. Phys. Chem. 2004, 108, 4040-4046.
40. L. Engman, A. Hallberg, J. Org. Chem. 1989, 54, 2964-2966.
41. a) M. Osajda, J. Młochowski, Tetrahedron, 2002, 58, 7531-7537;
42. b) A. Filipovska, G. F. Kelso, S. E. Brown, S. M. Beer, R. A. J. Smith, M. P. Murphy, J. Biol. Chem. 2005, 280, 24113-24126;
43. c) A. Welter, H. Fischer, L. Christiaens, A. Wendel, E. Etschenberg, Ger. Offen. 1986, pp. 26, Eur. Pat. Appl. CODEN: GWXXBX DE 3513070 A1 19861030 CAN 106:84181 AN 1987:84181 CAPLUS.
44. Gaussian 98, Revision A 11.3, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
45. a) C. Lee, W. Yang, R. G. Parr. Phys. Rev. B 1988, 37, 785-789;
46. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
47. W. Nakanishi, S. Hayashi, J. Phys. Chem. A 1999, 103, 6074-6081, and references therein.
48. a) A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926;
49. b) Natural Bond Orbital (NBO) Version 3.1), E. D. Glendening, J. E. Reed, J. E. Carpenter, F. Weinhold.
50. A. Altomare, G. Cascarano, C. Giacovazzo, A. Gualardi, J. Appl. Crystallogr. 1993, 26, 343-350.
51. a) G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473;
52. b) G. M. Sheldrick, SHELX-97, Program for refinement of crystal structures, University of Göttingen (Germany), 1997.
53. CCDC-616461 (16), CCDC-616460 (17), CCDC-616459 (18), CCDC-616462 (19), CCDC-616463 (20), and CCDC-626274 (22) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data. request/cif.