Synthesis of α-tocopherol analogues

Australian Journal of Chemistry

Volumn 50, Issue 12, 1997, Pages 1129-1135

  Suarna, Cacang ^a   Dean, Roger T ^a   Southwell Keely, Peter T ^b  

^a HEART RESEARCH INSTITUTE   (Australia)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009735486     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/C97044     Document Type: Article

References (62)

1. Marques, M. L. D., Cazana, F. J. L., and Puyol, M. R., Int. J. Vitam. Nutr. Res., 1987, 57, 375.
2. Steiner, M., and Anastasi, J., J. Clin. Invest, 1976, 57, 732.
3. Murty, H. S., Caasi, P. I., Brooks, S. K., and Nair, P. P., J. Biol Chem., 1970, 245, 5498.
4. Esterbauer, H., Dieber-Rotheneder, M., Striegl, G., and Waeg, G., Am. J. Clin. Nutr., 1991, 53, 314S.
5. Esterbauer, H., Gebicki, J., Puhl, H., and Jurgens, G., Free Radical Biol, Med., 1992, 13, 341.
6. Jessup, W., Rankin, S. M., De Whalley, C. V., Hoult, J. R., Scott, J., and Leake, D. S., Biochem. J., 1990, 265, 399.
7. Skinner, W. A., Johnson, H. L., Ellis, M., and Parkhurst, R. M., J. Pharm. Sci., 1971, 60, 643.
8. Tomassi, G., and Silano, V., Food Chem. Toxicol., 1986, 24, 1051.
9. Mukai, K., Kageyama, Y., Ishida, T., and Fukuda, K., J. Org. Chem., 1989, 54, 552.
10. Foote, C. S., Ching, T. Y., and Geller, G. G., Photochem. Photobiol., 1974, 20, 511.
11. Kaiser, S., Di Mascio, P., Murphy, M. E., and Sies, H., Arch. Biochem. Biophys., 1990, 277, 101.
12. Burton, G. W., Joyce, A., and Ingold, K. U., Arch. Biochem. Biophys., 1983, 221, 281.
13. van Acker, S. A. B. E., Koymans, L. M. H., and Bast, A., Free Radical Biol. Med., 1993, 15, 311.
14. Ingold, K. U., Burton, G. W., Foster, D. O., and Hughes, K. U., FEBS Lett, 1990, 267, 63.
15. Suarna, C., Hood, R., Dean, R. T., and Stocker, R., Biochim. Biophys. Acta, 1993, 1166, 163.
16. Hayes, K. C., Pronczuk, A., and Liang, J. S., Proc. Soc. Exp. Biol. Med., 1993, 202, 353.
17. Kagan, V. E., Serbinova, E. A., and Packer, L., Arch. Biochem. Biophys., 1990, 282, 221.
18. Burton, G. W., Doha, T., Gabe, E. J., Hughes, L., Lee, F. L., Prasad, L., and Ingold, K. U., J. Am, Chem. Soc., 1985, 107, 7053.
19. Thomas, S. M., Gebicki, J. M., and Dean, R. T., Biochim-Biophys. Acta, 1989, 1002, 189.
20. Bowry, V., Mohr, D., Cleary, J., and Stocker, R., J. Biol Chem., 1995, 270, 5756.
21. Dean, R. T., Jessup, W., and Roberts, C. R., Biochew. J., 1984, 217, 27.
22. Scott, J. W., Harley, H., Cort, W. M., Parrish, D. R., and Saucy, G., J. Am. Oil Chem. Soc., 1974, 51, 200.
23. Scott, J. W., and Cort, W. M., Cosmet. Toiletries, 1976, 91, 39, 42, 44.
24. Cort, W. M., Scott, J. W., Araujo, M., Mergens, W. J., Cannalonga, M. A., Osadca, M., Harley, H., Parrish, D. R., and Pool, W. R., J. Am. Oil Chem. Soc., 1975, 52, 174.
25. Dean, R. T., Hunt, J. V., Grant, A. J., Yamamoto, Y., and Niki, E., Free Radical Biol Med., 1991, 11, 161.
26. Neuzil, J., Gebicki, J. M., and Stocker, R., Biochem. J., 1993, 293, 601.
27. Cohen, N., Scott, J. W., Bizzarro, F. T., Lopresti, R., Eichel, W. F., and Saucy, G., Helv. Chim. Acta, 1978, 61, 837.
28. Cohen, N., Schaer, B., Saucy, G., Borer, R., Todaro, L., and Chiu, A. M., J. Org. Chem., 1989, 54, 3282.
29. Janero, D. A., Cohen, N., Burghardt, B., and Schaer, B. H., Biochem. Pharmaco., 1990, 40, 551.
30. Akkerman, J. M., de Koning, H., and Huisman, H. O., J. Chem. Soc., Perkin Trans, 1, 1979, 2124.
31. Yoshioka, T., Fujita, T., Kanai, T., Aizawa, Y., Kurumuda, T., Hasegawa, K., and Horikoshi, H., J. Med. Chem., 1989, 32, 421.
32. Ingold. K. U., Burton, G. W., Foster, D. O., Zuker, M., Hughes, L., Lacelle, S., Lusztyk, E., and Slaby, M., FEBS Lett., 1986, 205, 117.
33. Burton, G. W., Hughes, L., and Ingold, K. U., J. Am. Chem. Soc., 1983, 105, 5950.
34. Placer, Z., and Weichet, J., Nahrung, 1968, 12, 491 (Chem. Abstr., 1969, 70, 2500g).
35. Placer, Z., and Weichet, J., Nahrung, 1968, 12, 491 (Chem. Abstr., 1969, 70, 2500g).
36. Burlakova, E. B., Kukhtina, E. N., Ol'khovskaya, I. P., Sarycheva, I. K., Sinkina, E. B., and Khrapova, N. G., Biofizika, 1979, 24, 965 (Chem. Abstr., 1980, 92, 71446k).
37. Burlakova, E. B., Kukhtina, E. N., Ol'khovskaya, I. P., Sarycheva, I. K., Sinkina, E. B., and Khrapova, N. G., Biofizika, 1979, 24, 965 (Chem. Abstr., 1980, 92, 71446k).
38. Barclay, L. R. G., in 'Free Radicals in Synthesis and Biology' (Ed. F. Minisci) pp. 391-406 (Kluwer: Norwell, Massachusetts, 1989).
39. Bolkenius, F. N., Grisar, J. M., and De Jong, W., Free Radical Res. Commun., 1991, 14, 363,
40. Barclay, L. R. C., Can. J. Chem., 1993, 71, 1.
41. Pryor, W. A., Cornicelli, J. A., Devall, L. J., Tait, B., Trivedi, B. K., Witiak, D. T., and Wu, M., J. Org. Chem., 1993, 58, 3521.
42. Scott, J. W., Bizzarro, F. T., Parrish, D. R., and Saucy, G., Helv. Chim. Acta, 1976, 59, 292.
43. Koreeda, M., and Brown, L., J. Org. Chem., 1983, 48, 2122.
44. Chan, K. K., Cohen, N., De Noble, J. P., Specian, A. C., and Saucy, G., J. Org. Chem., 1976, 41, 3497.
45. Cohen, N., Eichel, W. F., Lopresti, R. J., Neukom, C., and Saucy, G., J. Org. Chem., 1976, 41, 3505.
46. Morita, T., Okamoto, Y., and Sakurai, H., J. Chem. Soc., Chem. Commun., 1978, 874.
47. Gassman, P. G., and Schenk, W. N., J. Org. Chem., 1977, 42, 918.
48. Cohen, N., Lopresti, R. J., and Saucy, G., J. Am. Chem. Soc., 1979, 101, 6710.
49. Brownstein, S., Burton, G. W., Hughes, L., and Ingold, K. U., J. Org. Chem., 1989, 54, 560.
50. Ratcliffe, R., and Rodehorst, R., J, Org. Chem., 1970, 35, 4000.
51. Barner, R., and Schmid, M., Helv. Chim. Acta, 1979, 62, 2384.
52. Grayson, M., and Keough, P. T., J. Am. Chem. Soc., 1960, 82, 3919.
53. Bissing, D. E., J. Org. Chem., 1965, 30, 1296.
54. Isler, O., Gutmann, H., Montavon, M., Ruegg, R., Ryser, G., and Zeller, P., Helv. Chim. Acta, 1957, 40, 1242.
55. Mayer, H., and Isler, O., Methods Enzymol., 1971, 18, (C), 241.
56. Schmid, M., and Barner, R., Helv. Chim. Acta, 1979, 62, 464.
57. Sondheimer, F., and Mechoulam, R., J. Am. Chem. Soc., 1957, 79, 5029.
58. Sondheimer, F., and Mechoulam, R., J. Am. Chem. Soc., 1958, 80, 3087.
59. Bestmann, H. J., and Schulz, H., Chem. Ber., 1962, 95, 2921.
60. Thomas, M. J., and Bielski, B. H. J., J. Am. Chem. Soc., 1989, 111, 3315.
61. Harada, T., Hayashiya, T., Wada, I., Iwa-ake, N., and Oku, A., J. Am. Chem. Soc., 1987, 109, 527.
62. Bravo, P., and Ticozzi, C., J. Heterocycl. Chem., 1978, 15, 1051.