Radical trapping properties of 3-aryl-2H-benzo[1,4]oxazin-4-oxides

Journal of Organic Chemistry

Volumn 72, Issue 23, 2007, Pages 8677-8682

  Astolfi, Paola ^a   Marini, Milvia ^a   Stipa, Pierluigi ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOXYL NITROGEN; AMINOXYLS; EPR SPECTROSCOPY; RADICAL TRAPPING PROPERTIES;

CARBON; DENSITY FUNCTIONAL THEORY; FREE RADICALS; NITROGEN; ORGANIC SOLVENTS; PARAMAGNETIC RESONANCE;

OXIDES;

2 NITROPHENOL; 2H BENZ[1,4]OXAZIN 4 OXIDE DERIVATIVE; AMINOXYL DERIVATIVE; BENZOXAZINE DERIVATIVE; BROMOACETIC ACID; CARBON; FREE RADICAL; NITRONE DERIVATIVE; ORGANIC SOLVENT; OXYGEN; SUPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; DENSITY FUNCTIONAL THEORY; ELECTRON SPIN RESONANCE; PARTITION COEFFICIENT; REACTION ANALYSIS; SPIN TRAPPING; STRUCTURE ANALYSIS;

ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NITROGEN OXIDES; OXAZINES; QUANTUM THEORY; SPIN TRAPPING; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 35948975053     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071212i     Document Type: Article

References (70)

1. (a) Mackor, A.; Wajer, Th. A. J. W.; de Boer, Th. J. Tetrahedron Lett. 1966, 2115.
2. (b) Iwamura, M.; Inamoto, N. Bull. Chem. Soc. Jpn. 1967, 40, 702.
3. (c) Chalfont, G. R.; Perkins, M. J.; Horsfield, A. J. Am. Chem. Soc. 1968, 90, 7141.
4. (d) Janzen, E. G.; Blackburn, B. J. J. Am. Chem. Soc. 1968, 90, 5909.
5. (e) Lagerscrantz, C.; Forshult, S. Nature 1968, 218, 1247.
6. (a) Janzen, E. G. Acc. Chem. Res. 1971, 4, 31.
7. (b) Evans, C. A. Aldrichimica Acta 1979, 12, 23.
8. (c) Mottley, C.; Mason, R. P. In Biological Magnetic Resonance 8; Berliner, L. J., Reuben, J., Eds.; Plenum Publishers: New York, 1989; p 489.
9. (d) Tordo, P. Electron Paramagn. Reson. 1998, 16, 116.
10. (e) Buettner, G. R. Free Radical Biol. Med. 1987, 3, 259.
11. (f) Janzen, E. G.; Liu, J. I.-P. J. Magn. Reson. 1973, 9, 510.
12. (g) Janzen, E. G.; Evans C. A.; Liu, J. l.-P. J. Magn. Reson. 1973, 9, 513.
13. (h) Janzen, E. G. In Free Radicals in Biology; Prior, W. A., Ed.; Academic Press: New York, 1980; p 115.
14. Kotake, Y.; Janzen, E. G. J. Am. Chem. Soc. 1991, 113, 9503.
15. (a) Makino, K.; Hagiwara, T.; Imaishi, H.; Nishi, M.; Fuji, S.; Ohya, H.; Murakami, A. Free Radical Res. Commun. 1990, 9, 233.
16. (b) Finkelstein, E.; Rosen, G. M.; Rauckman, E. J. Mol. Pharmacol. 1982, 21, 262.
17. (a) Hinton, R. D.; Janzen, E. G. J. Org. Chem. 1992, 57, 2646.
18. (b) Zeghdaoui, A.; Tuccio, B.; Finet, J.-P.; Cerri, V.; Tordo, P. J. Chem. Soc., Perkin Trans. I 1995, 2087.
19. (c) Janzen, E. G.; Zhang, Y.-K; Haire, D. L. Magn. Reson. Chem. 1994, 32, 711.
20. (d) Fréjaville, C.; Karoui, H.; Tuccio, B.; Le Moigne, F.; Culcasi, M.; Pietri, S.; Lauricella R.; Tordo, P. J. Chem. Soc., Chem. Commun. 1994, 1793.
21. (e) Fréjaville, C.; Karoui, H.; Tuccio, B.; Le Moigne, F.; Culcasi, M.; Pietri, S.; Lauricella R.; Tordo, P. J. Med. Chem. 1995, 38, 258.
22. (f) Stolze, K.; Udilova N.; Nohl, H. Biol. Chem. 2002, 383, 813.
23. (g) Stolze, K.; Udilova, N.; Rosenau, T.; Hofinger A.; Nohl, H. Biol. Chem. 2003, 384, 493.
24. (h) Zhao, H.; Joseph, J.; Zhang, H.; Karoui H.; Kalyanaraman, B. Free Radical Biol. Med. 2001, 31, 599.
25. (i) Olive, G.; Mercier, A.; Le Moigne, F.; Rockenbauer A.; Tordo, P. Free Radical Biol. Med. 2000, 28, 403.
26. (a) Tsai, P.; Pou, S.; Straus, R.; Rosen, G. M., J. Chem. Soc., Perkin Trans. 2 1999, 1759.
27. (b) Rosen, G. M.; Tsai, P.; Barth, E. D.; Dorey, G.; Casara, P.; Spedding, M.; Halpern, H. J. J. Org. Chem. 2000, 65, 4460.
28. (a) Dupeyre, R.-M.; Rassat, A. J. Am. Chem. Soc. 1966, 88, 3180.
29. (b) Adamic, K.; Bowman, D. F.; Gillan, T.; Ingold, K. U. J. Am. Chem. Soc. 1971, 93, 902.
30. (a) Karoui, H.; Nsanzumuhire, C.; Le Moigne, F.; Tordo, P. J. Org. Chem. 1999, 64, 1471.
31. (b) Allouch, A.; Roubaud, V.; Lauricella, R.; Bouteiller, J-C, Tuccio, B. Org. Biomol. Chem. 2005, 3, 2458.
32. (a) Parr, R. G.; Yang, W. In Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1998.
33. (b) Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, Germany, 2000.
34. For a review, see: Improta, R.; Barone, V. Chem. Rev. 2004, 104, 1231.
35. Battistoni, P.; Bruni, P.; Fava, G. Tetrahedron 1979, 35, 1771.
36. (a) Villamena, F. A.; Hadad, C. M.; Zweier, J. L. J. Am. Chem. Soc 2004, 126, 1816.
37. (b) Villamena, F.; Dickman, M. H.; Crist, D. R. Inorg. Chem. 1998, 37, 1446.
38. (c) Boeyens, J. C. A.; Krager, G. J. Acta Crystallogr. 1970, B26, 668.
39. (d) Xu, Y. K.; Chen, Z. W.; Sun, J.; Liu, K.; Chen, W.; Shi, W.; Wang, H. M.; Zhang, X. K.; Liu, Y. J. Org. Chem. 2002, 67, 7624.
40. Astolfi, P.; Stipa, P. Unpublished results.
41. MAD: average difference between the computed and experimental values ignoring the sign: Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods; Gaussian Inc.: Pittsburgh, PA 1996; p 145.
42. Villamena, F. A.; Merle, J. K.; Hadad, C. M.; Zweier J. L. J Phys. Chem. A 2005, 109, 6083.
43. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 193.
44. Batt, L.; Robinson, G. N. Int. J. Chem. Kinet. 1982, 14, 1053.
45. Berti, C.; Colonna, M.; Greci, L.; Marchetti, L. Tetrahedron 1975, 31, 1745.
46. Stipa, P. Chem. Phys. 2006, 323, 501.
47. Barone, V. In Recent Advances in Density Functional Methods; Chong, D. P., Ed.; World Scientific Publ. Co.: Singapore, 1966; Part 1.
48. (a) Di Matteo, A.; Adamo, C.; Cossi, M.; Barone, V.; Rey, P. Chem. Phys. Lett. 1999, 310, 159.
49. (b) Di Matteo, A.; Adamo, C.; Barone V.; Rey, P. J. Phys. Chem. 1999, 103, 3481.
50. (c) Di Matteo, A.; Bencini, A.; Cossi, M.; Barone, V.; Mattesini M.; Totti, F. J. Am. Chem. Soc. 1998, 120, 7069.
51. (d) Barone, V.; Grand, A.; Luneau, D.; Rey, P.; Minichino, C.; Subra, R. New J. Chem. 1993, 17, 545.
52. (e) Cirujeda, J;. Vidal-Gancedo, J.; Jürgens, O.; Mota, F.; Novoa, J. J.; Rovira C.; Veciana, J. J. Am. Chem. Soc. 2000, 122, 11393.
53. (f) Zheludev, A.; Barone, V.; Bonnet, M.; Delley, B.; Grand, A.; Ressouche, E.; Rey, P.; Subra, R.; Schweizer, J. J. Am. Chem. Soc. 1994, 116, 2019.
54. (g) Mattar, S. M.; Stephens, A. L. Chem. Phys. Lett. 2000, 319, 601.
55. Beyer, M.; Fritscher, J.; Feresin, E.; Schiemann, O. J. Org. Chem. 2003, 68, 2209.
56. Fischer, H. In Free Radicals; Kochi, J. K., Ed.; Wiley-Interscience: New York, 1973; Vol. II, p 435.
57. (a) Pou, S.; Halpern, H. J.; Tsai, P.; Rosen, G. M. Acc. Chem. Res. 1999, 32, 155.
58. (b) Halliwell B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 2nd ed.; Clarendon Press: Oxford, 1989.
59. (c) Korthuis, D.; Carden, D. L.; Granger, D. N. In Biological Consequences of Oxidative Stress; Spatz, L., Bloom, D., Eds.; Oxford Press: London, 1992; p 50.
60. (d) Schulz, J. B.; Henshaw, D. R.; Siwek, D.; Jenkins, B. G.; Ferrante, R. J.; Cipolloni, P. B.; Kowall, N. W.; Rosen B. R.; Beal, M. F. J. Neurochem. 1995, 64, 2239.
61. (e) Harbour, J. R.; Chow, V.; Bolton, J. R. Can. J. Chem. 1974, 52, 3549.
62. (f) Finkelstein, E.; Rosen, G. M.; Rauckman, E. J.; Paxton, J. Mol. Pharmacol. 1979, 16, 676.
63. (g) Kalyanaraman, B.; Perez-Reyes, E.; Mason, R. P. Biochim. Biophys. Acta 1980, 630, 119.
64. Stolze, K.; Udilova, N.; Nohl, H. Free Radical Biol. Med. 2000, 29, 1005.
65. Koronev, E. A.; Baker, J. E.; Joseph, J.; Kalyanaraman, B. Free Radical Biol. Med. 1993, 14, 127.
66. Turner, M. J., III; Rosen, G. M. J. Med. Chem. 1986, 29, 2439.
67. Rosen, G. M.; Finkelstein, E.; Raukman, E. J. Arch. Biochem. Biophys. 1982, 215, 367.
68. Duling, D. PEST Winsim, version 0.96; National Institute of Environmental Health Sciences: Triangle Park, NC, 1996.
69. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision D.02; Gaussian Inc.: Wallingford, CT, 2004.
70. Stipa, P.; Greci, L.; Carloni, P.; Damiani, E. Polym. Degrad. Stab. 1997, 55, 323.