Synthesis, structure, spirocyclization mechanism, and glutathione peroxidase-like antioxidant activity of stable spirodiazaselenurane and spirodiazatellurane

Journal of the American Chemical Society

Volumn 132, Issue 15, 2010, Pages 5364-5374

  Sarma, Bani Kanta ^a   Manna, Debasish ^a   Minoura, Mao ^b   Mugesh, Govindasamy ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ANTIOXIDANT ACTIVITIES; APICAL POSITIONS; CARBON ATOMS; CHIRAL RESOLUTIONS; EQUATORIAL POSITIONS; FAST OXIDATION; GLUTATHIONE PEROXIDASE; GPX MIMIC; LONE PAIR; MECHANISTIC STUDIES; NITROGEN ATOM; REDOX CYCLES; SELENIDES; SINGLE CRYSTAL X-RAY ANALYSIS; SPIRO COMPOUNDS; SPIROCYCLIZATION; X RAY CRYSTAL STRUCTURES;

ACTIVATION ENERGY; COMPLEXATION; CRYSTAL ATOMIC STRUCTURE; OXIDATION; PLANTS (BOTANY); REACTION INTERMEDIATES; SELENIUM; SELENIUM COMPOUNDS; SOLID ELECTROLYTES; SYNTHESIS (CHEMICAL); TELLURIUM; TELLURIUM COMPOUNDS;

CYCLIZATION;

2,2 SELENOBIS(BENZANILIDE); 2,2 TELLUROBIS(BENZANILIDE); CHALCOGEN; GLUTATHIONE PEROXIDASE; NITROGEN; PEROXIDE; SELENIUM DERIVATIVE; SPIRODIAZASELENURANE; SPIRODIAZATELLURANE; SULFUR DERIVATIVE; TELLURIUM DERIVATIVE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTIOXIDANTS; CYCLIZATION; FREE RADICAL SCAVENGERS; GLUTATHIONE PEROXIDASE; ORGANOMETALLIC COMPOUNDS; ORGANOSELENIUM COMPOUNDS; OXIDATION-REDUCTION; PEROXYNITROUS ACID; SELENIUM; TELLURIUM; THERMODYNAMICS;

EID: 77951084422     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja908080u     Document Type: Article

References (97)

1. Kapovits, I. and Kálmán, A. Chem. Commun. 1971, 649-650
2. Martin, J. C. and Perozzi, E. F. Science 1976, 191, 154-159
3. Martin, J. C. Science 1983, 221, 509-514
4. Hayes, R. A. and Martin, J. C. In Sulfurane Chemistry; Bernardi, F., Csizmadia, I. G., and Mangini, A. Elsevier: Amsterdam, 1985; pp 408 - 483.
5. Drabowicz, J., Lyzwa, P., and Mikolajczyk, M. In High-Coordinated Sulfur Compounds; Patai, S. and Rappoport, Z. Wiley: New York, 1993; pp 799 - 956.
6. Drabowicz, J. and Martin, J. C. Pure Appl. Chem. 1996, 68, 951-956
7. Drabowicz, J. In Hypervalent Sulfuranes As Transient and Isolable Structures: Occurrence, Synthesis and Reactivity; Akiba, K.-Y. Wiley: New York, 1999; pp 211 - 240.
8. Furukawa, N. and Sato, S. Top. Curr. Chem. 1999, 205, 89-129
9. Takaguchi, Y. and Furukawa, N. Heteroat. Chem. 1995, 6, 481-484
10. Furukawa, N. and Sato, S. In Structure and Reactivity of Hypervalent Chalcogen Compounds: Selenurane (Selane) and Tellurane (Tellane); Akiba, K.-Y., Eds.; Wiley: New York, 1999; pp 241 - 278.
11. Drabowicz, J. and Halaba, G. Rev. Heteroat. Chem. 2000, 22, 1-32
12. Takaguchi, Y. and Furukawa, N. Chem. Lett. 1996, 5, 365-366
13. Zhang, J., Takahashi, S., Saito, S., and Koizumi, T. Tetrahedron: Asymmetry 1998, 9, 3303-3317
14. Ohno, F., Kawashima, T., and Okazaki, R. Chem. Commun. 2001, 463-464
15. Kano, N., Takahashi, T., and Kawashima, T. Tetrahedron Lett. 2002, 43, 6775-6778
16. Ohno, F., Kawashima, T., and Okazaki, R. Chem. Commun. 1997, 17, 1671-1672
17. Allenmark, S. Chirality 2008, 20, 544-551, and references therein
18. Lesser, R. and Weiss, R. V. Ber. Dtsch. Chem. Ges. 1914, 47, 2510-2525
19. Zhang, J., Saito, S., and Koizumi, T. J. Org. Chem. 1998, 63, 9375-9384
20. Zhang, J., Saito, S., and Koizumi, T. J. Am. Chem. Soc. 1998, 120, 1631-1632
21. Zhang, J., Takahashi, S., Saito, S., and Koizumi, T. Tetrahedron: Asymmetry 1998, 9, 3303-3317
22. Kapovits, I., Rábai, J., Szabó, D., Czakó, K., Kucsman, Á., Argay, G., Fülöp, V., Kálmán, A., Koritsánsky, T., and Párkányi, L. J. Chem. Soc., Perkin Trans. 2 1993, 847-853
23. Szókán, G., Szarvas, S., Majer, Z., Szabó, D., Kapovits, I., and Hollósi, M. J. Liq. Chromatogr. 1999, 22, 993-1007
24. Kapovits, I., Rábai, J., Ruff, F., and Kucsman, Á. Tetrahedron 1979, 35, 1869-1874
25. Martin, J. C. and Perozzi, E. F. J. Am. Chem. Soc. 1974, 96, 3155-3168
26. Adzima, L. J. and Martin, J. C. J. Org. Chem. 1977, 42, 4006-4016
27. Kapovits, I., Rabai, J., Ruff, F., Kucsman, Á., and Tanács, B. Tetrahedron 1979, 35, 1875-1881
28. Martin, J. C. and Arhart, R. J. J. Am. Chem. Soc. 1971, 93, 2339-2341
29. Martin, J. C. and Arhart, R. J. J. Am. Chem. Soc. 1971, 93, 2341-2342
30. Arhart, R. J. and Martin, J. C. J. Am. Chem. Soc. 1972, 94, 4997-5003
31. Perozzi, E. F. and Martin, J. C. J. Am. Chem. Soc. 1972, 94, 5519-5520
32. Kálmán, A., Sasvári, K., and Kapovits, I. Acta Crystallogr. Sect. B 1973, 29, 355-357
33. Vass, E., Ruff, F., Kapovits, I., Rábai, J., and Szabó, D. J. Chem. Soc., Perkin Trans. 2 1993, 855-859
34. Back, T. G., Moussa, Z., and Parvez, M. Angew. Chem., Int. Ed. 2004, 43, 1268-1270
35. Flohé, L., Günzler, E. A., and Schock, H. H. FEBS Lett. 1973, 32, 132-134
36. Rotruck, J. T., Pope, A. L., Ganther, H. E., Swanson, A. B., Hafeman, D. G., and Hoekstra, W. G. Science 1973, 179, 588-590
37. Epp, O., Ladenstein, R., and Wendel, A. Eur. J. Biochem. 1983, 133, 51-69
38. Jacob, C., Giles, G. I., Giles, N. M., and Sies, H. Angew. Chem., Int. Ed. 2003, 42, 4742-4758
39. Back, T. G., Kuzma, D., and Parvez, M. J. Org. Chem. 2005, 70, 9230-9236
40. Tripathi, S. K., Patel, U., Roy, D., Sunoj, R. B., Singh, H. B., Wolmershäuser, G., and Butcher, R. J. J. Org. Chem. 2005, 70, 9237-9247
41. Adzima, L. J. and Martin, J. C. J. Org. Chem. 1977, 42, 4006-4016
42. Adzima, L. J., Chiang, C. C., Paul, I. C., and Martin, J. C. J. Am. Chem. Soc. 1978, 100, 953-962
43. Szabó, D., Adám, T., and Kapovits, I. Sulfur Lett. 1997, 21, 21-34
44. Szabó, D., Kuti, M., Kapovits, I., Rábai, J., Kucsman, A., Argay, G., Czugler, M., Kálmán, A., and Párkányi, L. J. Mol. Struct. 1997, 415, 1-16
45. Adám, T., Ruff, F., Kapovits, I., Szabó, D., and Kucsman, A. J. Chem. Soc., Perkin Trans. 2 1998, 1269-1275
46. Kuzma, D., Parvez, M., and Back, T. G. Org. Biomol. Chem. 2007, 5, 3213-3217
47. For excellent articles on Se⋯X (X = N, O, Cl, Br, F, etc.) interactions, see:.
48. Iwaoka, M. and Tomoda, S. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 67, 125-130
49. Iwaoka, M. and Tomoda, S. J. Am. Chem. Soc. 1994, 116, 2557-2561
50. Iwaoka, M. and Tomoda, S. J. Am. Chem. Soc. 1996, 118, 8077-8084
51. Iwaoka, M., Komatsu, H., and Tomoda, S. Chem. Lett. 1998, 969-970
52. Wirth, T., Fragale, G., and Spichty, M. J. Am. Chem. Soc. 1998, 120, 3376-3381
53. Komatsu, H., Iwaoka, M., and Tomoda, S. Chem. Commun. 1999, 205-206
54. Spichty, M., Fragale, G., and Wirth, T. J. Am. Chem. Soc. 2000, 122, 10914-10916
55. Iwaoka, M., Komatsu, H., Katsuda, T., and Tomoda, S. J. Am. Chem. Soc. 2002, 124, 1902-1909
56. Iwaoka, M., Katsuda, T., Tomoda, S., Harada, J., and Ogawa, K. Chem. Lett. 2002, 518-519
57. Iwaoka, M., Komatsu, H., Katsuda, T., and Tomoda, S. J. Am. Chem. Soc. 2004, 126, 5309-5317
58. Iwaoka, M., Katsuda, T., Komatsu, H., and Tomoda, S. J. Org. Chem. 2005, 70, 321-327
59. Bayse, C. A., Baker, R. A., and Ortwine, K. N. Inorg. Chim. Acta 2005, 358, 3849-3854
60. Roy, D. and Sunoj, R. B. J. Phys. Chem. A 2006, 110, 5942-5947
61. Barton, D. H. R., Hall, M. B., Lin, Z., Parekh, S. I., and Reibenspies, J. J. Am. Chem. Soc. 1993, 115, 5056-5059
62. Panda, A., Menon, S. C., Singh, H. B., and Butcher, R. J. J. Organomet. Chem. 2001, 623, 87-94
63. Panda, A., Mugesh, G., Singh, H. B., and Butcher, R. J. Organometallics 1999, 18, 1986-1993
64. The aerial oxidation of the telluride 21 to spirodiazatellurane (25) is not surprising, as the aerial oxidation of certain tellurides to spirodioxytellurane is well documented in the literature. For details, see ref 2a.
65. Flack, H. Acta Crystallogr., Sect. A 1983, 39, 876-881
66. 125Te NMR in the presence of chiral shift reagent indicated the presence of two enantiomers (Figure S31, Supporting Information).
67. Sarma, B. K. and Mugesh, G. J. Am. Chem. Soc. 2005, 127, 11477-11485, and references therein
68. Lee, C., Yang, W., and Parr, R. G. Phys. Rev. B 1988, 37, 785-789
69. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
70. Hay, P. J. and Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283
71. Hay, P. J. and Wadt, W. R. J. Chem. Phys. 1985, 82, 284-298
72. Hay, P. J. and Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310
73. Check, C. E., Faust, T. O., Bailey, J. M., Wright, B. J., Gilbert, T. M., and Sunderlin, L. S. J. Phys. Chem. A 2001, 105, 8111-8116
74. Reed, A. E., Curtiss, L. A., and Weinhold, F. Chem. Rev. 1988, 88, 899-926
75. Glendening, E. D., Reed, J. E., Carpenter, J. E., and Weinhold, F. NBO Program 3.1; Madison, WI, 1988.
76. It should be noted that in the case of tellurium one more intermediate (23INT2b) was observed between the first intermediate (23INT1) and the stable intermediate having N-Se-OH ≈ 180° (23INT3b) (Table 2). However, this intermediate (23INT2b) converts to 23INT3b via transition state 23TS3b, having no activation energy barrier. Therefore, it is not surprising that we have not observed any such intermediates in the case of sulfur and selenium.
77. 2 O failed, and every time the transition state optimization converged to the transition state 23TS3a of pathway (a) water elimination was involved. Further, we observed that 23INT3b converts to 23INT2a via transition state 23TS4b. This indicates that pathway (b) merges with pathway (a) and pathway (a) is the one that leads to the formation of a spiro compound.
78. Back, T. G. and Moussa, Z. J. Am. Chem. Soc. 2002, 124, 12104-12105
79. Back, T. G. and Moussa, Z. J. Am. Chem. Soc. 2003, 125, 13455-13460
80. Sies, H. and Masumoto, H. Adv. Pharmacol. 1997, 38, 229-246
81. Mugesh, G. and Singh, H. B. Chem. Soc. Rev. 2000, 29, 347-357
82. Mugesh, G., du Mont, W.-W., and Sies, H. Chem. Rev. 2001, 101, 2125-2179, and references therein
83. Noguira, C. W., Zeni, G., and Rocha, J. B. T. Chem. Rev. 2004, 104, 6255-6286
84. 1/2 for 24 (62 h) as compared to that of 20 (88 h) is not because of the regeneration of 24 in the catalytic cycle, but is due to the initial ∼20% conversion of BnSH to BnSSBn, which arises from the direct reaction of BnSH with 24 during the first ∼140 min.
85. Andersson, C. M., Hallberg, A., Brattsand, R., Cotgreave, I. A., Engman, L., and Persson, J. Bioorg. Med. Chem. Lett. 1993, 3, 2553-2558
86. Giles, G. I., Fry, F. H., Tasker, K. M., Holme, A. L., Peers, C., Green, K. N., Klotz, L.-O., Sies, H., and Jacob, C. Org. Biomol. Chem 2003, 1, 4317-4322
87. Masumoto, H., Kissner, R., Koppenol, W. H., and Sies, H. FEBS Lett. 1996, 398, 179-182
88. It should be noted that the tellurium analogue of ebselen (ebtellur) is not known, although ebtellur has been used as a model compound for computational studies to understand the reactivity of organotellurium compounds toward reactive oxygen species such as peroxynitrite. Therefore, the spiro analogue of ebtellur (25) may help clarify the effect of tellurium substitution in cyclic selenazole-based compounds. For theoretical studies on ebtellur and related compounds, see: Sakimoto, Y., Hirao, K., and Musaev, D. G. J. Phys. Chem. A 2003, 107, 5631-5639
89. Musaev, D. G. and Hirao, K. J. Phys. Chem. A 2003, 107, 9984-9990
90. Foss, O. Inorg. Synth. 1953, 4, 88-93
91. Di Mascio, P., Bechara, E. J. H., Medeiros, M. H. G., Briviba, K., and Sies, H. FEBS Lett. 1994, 355, 287-289
92. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004. The full reference is given in the Supporting Information.
93. Fukui, K. Acc. Chem. Res. 1981, 14, 363-368
94. SMART, Version 5.05; Bruker AXS: Madison, WI, 1998.
95. Altomare, A., Cascarano, G., Giacovazzo, C., and Gualardi, A. J. Appl. Crystallogr. 1993, 26, 343-350
96. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467-473
97. Sheldrick, G. M. SHELX-97, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.