Synthesis and photooxidation of sodium 1,3-cyclohexadiene-1,4-diethanoate: A new colorless and water-soluble trap of singlet oxygen

Tetrahedron

Volumn 52, Issue 6, 1996, Pages 2031-2046

  Nardello, Véronique ^a   Azaroual, Nathalie ^a   Cervoise, Isabelle ^a   Vermeersch, Gaston ^a   Aubry, Jean Marie ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; SINGLET OXYGEN; SODIUM 1,3 CYCLOHEXADIENE 1,4 DIETHANOATE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DETERMINATION; DRUG SYNTHESIS; PHOTOCHEMISTRY; PRIORITY JOURNAL; TECHNIQUE;

EID: 0030046904     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01004-1     Document Type: Article

References (61)

1. Matsumoto, M. Singlet Oxygen, Frimer, A. A. Ed. CRC Press, Boca Raton, Fl. 1985, 2, 205.
2. Aubry J. M. J. Am. Chem. Soc. 1985, 107, 5844-5849.
3. Murray, R. W. Singlet Oxygen, Wasserman, H. H.; Murray, R. W. Eds., Academic Press: New York, 1979, pp 59-114.
4. Barton, D. H. R; Magnus P. D.; Quinney J. C.; J. Chem. Soc. Perkin Trans. 1975, 1, 1610-1614.
5. Sugimoto, H.; Sawyer, D. T. J. Am. Chem. Soc. 1984, 106, 4283-4285.
6. Aubry J. M.; Cazin B. Inorg. Chem. 1988, 27, 2013.
7. Zepp, R. G.; Wolfe, N. L.; Baughman, G. L.; Hollis, R. C. Nature, 1977, 267, 421-423.
8. Garcia, N. A. J. Photochem. Photobiol. B: Biol. 1994, 22, 185-196.
9. Khan, A. U. J. Am. Chem. Soc. 1983, 105, 7195.
10. Kanofsky, J. R. J. Biol. Chem. 1983, 258, 5991.
11. Kanofsky, J. R. J. Photochem. 1984, 25, 105.
12. Kanofsky, J. R.; Wright, J.; Miles-Richardson, G. E.; Tauber, A. I. J. Clin. Invest. 1984, 74, 1489.
13. Gallo, U.; Santamaria, L. 'Research Progress in Organic Biological and Medicinal Chemistry', Am. Elsevier, New York, 1972, 3.
14. Spikes, J. D.; Livingston, R. Adv. Radiat. Biol. 1969, 3, 29.
15. Spikes, J.; Macknight, M. L. Ann. N. Y. Acad. Sci. 1970, 777, 149.
16. Foote, C. S. Free Radicals in Biology, Pryor, W. A. Ed. Academic Press, New York, 1979, 1.
17. Gross Weiner, L. I. Curr. Top. Radiat. Res. Q. 1976, 11, 141.
18. Gorman, A. A.; Rodgers, M. A. J. J. Photochem. Photobiol. B: Biol. 1992, 14, 159-176.
19. Foote, C. S. Free Radicals in Biology, Pryor, W. A. Ed. Academic Press, New York, 1976, 2, 85.
20. Straight, R. C.; Spikes, J. D. Singlet Oxygen, Frimer, A. A. Ed. CRC Press, Boca Raton, Fl, 1985, 4, pp 91-143.
21. Weishaupf, K. R.; Gomer, C. J.; Dougherty, T. J. Cancer Res. 1976, 36, 2326-2329.
22. Photodynamic Therapy of Neoplastic Disease, Kessel, D. Ed., CRC Press, Boston, 1990.
23. North, J.; Neyndorff, H.; Levy, J. G. J. Photochem. Photobiol. B. 1993, 17, 99-108.
24. Smith, L.L.; Kulig, M. J. J. Am. Chem. Soc. 1976, 98, 1027.
25. Smith, L. L.; Shoud, J. P. Photochem. Photobiol. 1978, 28, 479-485.
26. Smith, L. L.; Teng, J. I.; Kulig, M. J.; Hill, F. L. J. Org. Chem. 1973, 38, 1763.
27. Korytowski, W; Bachowski, G. J.; Girotti, A. W. Photochem. Photobiol. 1992, 1, 1-8.
28. Foote, C. S.; Shook, F. C.; Abakerli, R. B. Methods in enzymology, 1984, 105, 36-47.
29. Foote, C. S.; Shook, F. C.; Abakerli, R. B. J. Am. Chem. Soc., 1980, 102, 2503.
30. Held, A. M.; Halko, D. J; Hurst, J. K. J. Am. Chem. Soc. 1978, 100, 5732.
31. Usui, Y.; Kamogawa, K. Photochem. Photobiol. 1974, 19, 245-247.
32. Foote, C. S. Biochemical and Clinical Aspects of Oxygen, Caughey, W. S. Ed. Academic Press, New York, 1979, pp 603-632.
33. Graf, G. A.; Braun, A. M.; Faure, J. Chimia, 1980, 34, 234-236.
34. Maurette, M. T.; Oliveros, E.; Infelta, P. P.; Ramsteiner, K.; Braun, A. M. Helv. Chim. Acta, 1983, 66, 722-723.
35. Murasecco, P.; Oliveros, E.; Braun, A. M.; Mormier, P. Photochemistry and Photobiophysics, 1985, 9, 193-201.
36. Giraud, M.; Valla, A.; Bazin, M.; Santus, R.; Momzikoff, A. J. Chem. Soc. Chem. Comm. 1982, 1147-1148.
37. Aubry, J. M.; Rigaudy, J.; Cuong, N. K. Photochem. Photobiol. 1981, 33, 149-153.
38. Schaap, A. P.; Thayer, A. L.; Faler, G. R.; Goda, K.; Kimura, T. J. Am. Chem. Soc. 1974, 96, 4025.
39. Aubry, J. M.; Rigaudy, J.; Ferradini, G.; Pucheault, J. J. Am. Chem. Soc. 1971, 103, 4965.
40. Botsivali, M.; Evans, D. F. J. Chem. Soc. Chem. Comm. 1979, 1114-1116.
41. Evans, D. F.; Upton, M. W. J. Chem. Soc. Dalton-Trans. 1985, 2525.
42. Linding, B. A.; Rodgers, M. A. J.; Schaap, A. P. J. Am. Chem. Soc. 1980, 702, 5590-5593.
43. Schaap, A. P.; Thayer, A. L.; Zaklika, K. A.; Valenti, P. C. Ibid. 1979, 101, 4016.
44. Rigaudy, J.; Guillaume, J.; Cuong, N. K. C.R. Acad. Sci. Paris, 1964, 259, 4729.
45. Rigaudy, J.; Ricard, M. Tetrahedron, 1968, 24, 3241.
46. Schmitz, C.; Aubry, J. M.; Rigaudy, J. Tetrahedron, 1982, 38, 1425-1430.
47. Müller, K.; Ziereis, K. Arch. Pharm. 1993, 326, 369-371.
48. Saito, I.; Matsuura, I.; Inoue, K. J. Am. Chem. Soc. 1981, 103, 188.
49. Saito, I.; Matsuura, I.; Inoue, K. J. Am. Chem. Soc. 1983, 105, 3200.
50. Nieuwint, A. W. M.; Aubry, J. M.; Arwert, F.; Kortbeek, U.; Herzberg, S.; Joenje, H. Free Radical Res. Commun. 1985, 1, 1.
51. Aubry, J. M.; Cazin, B.; Duprat, F. J. Org. Chem. 1989, 54, 726.
52. Marcel, C. S.; Wilson, B. D. J. Org. Chem. 1958, 23, 1483-1488.
53. Aubry, J. M. New Chemical Sources of Singlet Oxygen. Menbrane Lipid Oxidation, Vol. II, Vigo-Pelfrey, Ed. CRC Press, Boca Raton, 1991, pp 65-102.
54. Engel, P. S.; Allgren, R. L.; Chae, W-K.; Leckonby R. A.; Marron, N. A. J. Org. Chem. 1979, 44, 4233.
55. Vever-Bizet, C.; Dellinger, M.; Brault, D.; Rougee, M.; Bensasson, R. V. Photochem. Photobiol. 1989, 50, 321.
56. Wilkinson, F.; Brummer, J. G. J. Phys. Chem. Ref. Data, 1981, 10, 809-999.
57. Gormann, A. A.; Rodgers, M. A. J. Singlet Oxygen in Handbook of Organic Photochemistry, Vol II; Scaiano, J. C.,Ed. CRC Press, Boca Raton, 1989, pp 229-247.
58. Aubry, J. M.; Mandard-Cazin, B.; Rougee, M.; Bensasson, R. J. Am. Chem. Soc. 1995, 777, 9159-9164.
59. Aubry, J. M.; Rigaudy, J.; Cuong, N. K. Photochem. Photobiol. 1981, 33, 155-158.
60. Matusch, R.; Schmidt, G. Angew. Chem. Int. Ed. Eng. 1988, 27, 717-718.
61. Clennan, E. L. Tetrahedron, 1991, 47, 1343-1382.