Synthesis and glutathione peroxidase-like activities of isoselenazolines

European Journal of Organic Chemistry

Volumn , Issue 28, 2011, Pages 5485-5497

  Singh, Vijay P ^a   Singh, Harkesh B ^a   Butcher, Ray J ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b HOWARD UNIVERSITY   (United States)

Author keywords

Antioxidants; Ebselen; Enzyme mimics; Heterocycles; Selenium; Structure activity relationships

Indexed keywords

EID: 80053203512     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100899     Document Type: Article

References (74)

1. See the Supporting Information for further details of the synthesis, full characterization and NMR spectra for all compounds.: A. Müller, E. Cadenas, P. Graf, H. Sies, Biochem. Pharmacol. 1984, 33, 3235-3239.
2. A. Wendel, M. Fausel, H. Safayhi, G. Tiegs, R. Otter, Biochem. Pharmacol. 1984, 33, 3241-3245.
3. M. J. Parnham, S. Kindt, Biochem. Pharmacol. 1984, 33, 3247-3250.
4. A. Müller, H. Gabriel, H. Sies, Biochem. Pharmacol. 1985, 34, 1185-1189.
5. H. Safayhi, G. Tiegs, A. Wendel, Biochem. Pharmacol. 1985, 34, 2691-2694.
6. A. Wendel, European Patent 0-165-534, 1985.
7. A. Wendel, G. Tiegs, Biochem. Pharmacol. 1986, 35, 2115-2118.
8. T. Schewe, Gen. Pharmacol. 1995, 26, 1153-1169.
9. M. J. Parnham, H. Sies, Expert Opin. Invest. Drugs 2000, 9, 607-619.
10. G. Mugesh, H. B. Singh, Chem. Soc. Rev. 2000, 29, 347-357.
11. G. Mugesh, W.-W. du Mont, H. Sies, Chem. Rev. 2001, 101, 2125-2179.
12. L. Flohè, E. A. Günzler, H. H. Schock, FEBS Lett. 1973, 32, 132-134.
13. J. T. Rotruck, A. L. Pope, H. E. Ganther, A. B. Swanson, D. G. Hafeman, W. G. Hoekstra, Science 1973, 179, 588-590.
14. C. Jacob, G. I. Giles, N. M. Giles, H. Sies, Angew. Chem. Int. Ed. 2003, 42, 4742-4758.
15. R. Lesser, R. Weiss, Ber. Dtsch. Chem. Gen. 1924, 57, 1077-1082.
16. R. Weber, M. Renson, Bull. Soc. Chim. Fr. 1976, 1124-1126.
17. A. Welter, L. Christiaens, P. Wirtz, Eur. Pat. Appl. EP 44453, 1982.
18. L. Engman, A. Hallberg, J. Org. Chem. 1989, 54, 2964-2966.
19. M. C. Fong, C. H. Schiesser, Tetrahedron Lett. 1995, 36, 7329-7332.
20. M. C. Fong, C. H. Schiesser, J. Org. Chem. 1997, 62, 3103-3108.
21. S. J. Balkrishna, B. S. Bhakuni, D. J. Chopra, K. Sangit, Org. Lett. 2010, 12, 5394-5397.
22. B. K. Sarma, G. Mugesh, J. Am. Chem. Soc. 2005, 127, 11477-11485.
23. K. P. Bhabak, G. Mugesh, Chem. Eur. J. 2007, 13, 4594-4601.
24. B. K. Sarma, G. Mugesh, Chem. Eur. J. 2008, 14, 10603-10614.
25. K. P. Bhabak, G. Mugesh, Chem. Eur. J. 2009, 15, 9846-9854.
26. K. P. Bhabak, G. Mugesh, Chem. Asian J. 2009, 4, 974-983.
27. K. Satheeshkumar, G. Mugesh, Chem. Eur. J. 2011, 17, 4849-4857.
28. T. Fenner, C. H. Schiesser, Molecules 2004, 9, 472-479.
29. H. J. Reich, C. P. Jasperse, J. Am. Chem. Soc. 1987, 109, 5549-5551.
30. P. Cotelle, P. Chan, N. Cotelle, J. L. Bernier, J. P. Henichart, J. Chim. Phys.-Chim. Biol. 1992, 89, 191-198.
31. A. Mohsine, L. Christiaens, Heterocycles 1996, 43, 2567-2593.
32. P. V. Jacquemin, L. E. Christiaens, M. J. Renson, M. J. Evers, N. Dereu, Tetrahedron Lett. 1992, 33, 3863-3866.
33. J. Chaudiere, I. Erdelmeier, M. Moutet, J.-C. Yadan, Phosphorus Sulfur Silicon Relat. Elem. 1998, 136, 137 & 138, 467-470.
34. J. Chaudière, J.-C. Yadan, I. Erdelmeier, C. Tailhan-Lomont, M. Moutet, in: Oxidative processes and Antioxidants (Ed.:, R. Paoletti), Ravan Press, New York, 1994, p. 165.
35. I. Erdelmeier, M. Moutet, J.-C. Yadan, J. Org. Chem. 2000, 65, 8152-8157.
36. C. Lambert, L. Christiaens, Tetrahedron 1991, 47, 9053-9060.
37. M. J. Parnham, J. Biedermann, Ch. Bittner, N. Dereu, S. Leyck, H. Wetzig, Agents Actions 1989, 27, 306-308.
38. B. Dakova, L. Lamberts, M. Evers, N. Dereu, Electrochim. Acta 1991, 36, 631-637.
39. J. K. Pearson, R. J. Boyd, J. Phys. Chem. A 2008, 112, 1013-1017.
40. B. Kersting, M. DeLion, Z. Naturforsch., Teil B 1999, 54, 1042-1047.
41. S. S. Zade, S. Panda, S. K. Tripathi, H. B. Singh, G. Wolmershauser, Eur. J. Org. Chem. 2004, 3857-3864.
42. G. Roy, G. Mugesh, J. Am. Chem. Soc. 2005, 127, 15207-15217.
43. T. G. Back, B. P. Dyck, J. Am. Chem. Soc. 1997, 119, 2079-2083.
44. V. P. Singh, H. B. Singh, R. J. Butcher, Eur. J. Inorg. Chem. 2010, 637-647.
45. V. P. Singh, H. B. Singh, R. J. Butcher, Chem. Commun. 2011, 47, 7221-7223.
46. A. Burger, A. C. Schmalz, J. Org. Chem. 1954, 19, 1841-1846.
47. M. Iwaoka, T. Katsuda, H. Komatsu, S. Tomoda, J. Org. Chem. 2005, 70, 321-327.
48. M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 1996, 118, 8077-8084.
49. C. A. Bayse, Inorg. Chem. 2004, 43, 1208-1210.
50. M. Iwaoka, H. Komatsu, T. Katsuda, S. Tomoda, J. Am. Chem. Soc. 2004, 126, 5309-5317.
51. W. Nakanishi, S. Hayashi, S. Toyota, Chem. Commun. 1996, 371.
52. W. Nakanishi, S. Hayashi, A. Sakaue, G. Ono, Y. Kwada, J. Am. Chem. Soc. 1998, 120, 3635-3640.
53. V. P. Singh, H. B. Singh, R. J. Butcher, Chem. Asian J. 2011, 6, 1431-1442 and references cited therein.
54. A. Bondi, J. Phys. Chem. 1964, 68, 441-445.
55. L. Dupont, O. Dideberg, P. Jacqemin, Acta Crystallogr., Sect. C 1990, 46, 484-486.
56. L. Dupont, O. Dideberg, M. Sbit, N. Dereu, Acta Crystallogr., Sect. C 1988, 44, 2159-2161.
57. K. P. Bhabak, G. Mugesh, Chem. Eur. J. 2008, 14, 8640-8651.
58. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926.
59. F. Weinhold, Natural Bond Orbital (NBO), version 5.0.
60. R. W. F. Bader, Atoms in Molecules: A Quantum Theory, Oxford University Press, New York, 1990.
61. F. Beigler-Konig, J. Schonbohm, D. Bayles, J. Comput. Chem. 2001, 22, 545-559.
62. P. Popelier, Atoms In Molecules: An Introduction; Pearson, Harlow, 2000.
63. F. C. Whitmore, P. J. Culhane, J. Am. Chem. Soc. 1929, 51, 602-605.
64. L. K. A. Rahman, R. M. Scrowston, J. Chem. Soc. Perkin Trans. 1 1984, 385-390.
65. D. D. Perrin, W. L. F. Armarego, Purification of Labratory Chemicals, Pergamon Press, 4th ed., 1996.
66. S. R. Wilson, P. A. Zucker, R.-R. C. Huang, A. Spector, J. Am. Chem. Soc. 1989, 111, 5936-5939.
67. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Determination, University of Göttingen, Germany, 1974.
68. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nikai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Commi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrazewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghabachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, rev. C.02, Gaussian, Inc., Wallingford, CT, 2004.
69. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
70. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
71. P. von Rague Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318.
72. P. von Rague Schleyer, M. Manoharan, Z.-X. Wang, B. Kiran, H. Jiao, R. Puchta, N. J. R. van Eikema Hommes, Org. Lett. 2001, 3, 2465-2468.
73. Z. Chen, C. S. Wannere, C. Corminboeuf, R. Puchta, P. von Rague Schleyer, Chem. Rev. 2005, 105, 3842-3888.
74. E. Kleinpeter, S. Klod, A. Koch, THEOCHEM 2007, 811, 45-60.