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Chiral Analogs of a-tocopherol. Antioxidant Activity of the (R) and (S) Enantiomers of {2-[6-hydroxy-2,5,7,8-tetramethylchroman-2-yl]ethyl}-trimethylammonium-p-toluenesulfonate Depending on Their Configuration

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Pharmaceutical Chemistry Journal Aims and scope

Starting with the (R) and (S) enantiomers of 2-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)ethanol, prepared previously by partial acylation of the corresponding racemic alcohol in the presence of the most easily available lipase, from the yeast Candida cylindracea, a four-stage syntheses was developed for both enantiomers of {2-[6-hydroxy-2,5,7,8-tetramethylchroman-2-yl]ethyl}trimethylammonium p-toluenesulfonate (MDL-73404), which are chiral analogs of α-tocopherol. Comparative biomedical testing of samples of MDL-73404 salts with different enantiomer compositions in relation to their effects on the generation of reactive oxygen species by peritoneal macrophages from white rats in systems containing luminol or lucigenin demonstrated different levels of inhibition of spontaneous and 12-O-myristyl-13-O-acetylphorbol-activated macrophage chemiluminescence.

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References

  1. E. Lubin and L. J. Machlin (eds.), Ann. N. Y. Acad. Sci., 393, 1 – 506 (1982).

  2. M. J. Kelly, in: Progress of Medicinal Chemistry, G. P. Ellis and G. B. West (eds.), Elsevier, Amsterdam (1988), Vol. 25, pp. 249 – 290.

  3. L. J. Machlin, in: Handbook of Vitamins, L. J. Machlin (ed.), Marcel Dekker, New York (1991), pp. 99 – 144.

  4. T. Netscher, in: Lipid Synthesis and Manufacture, F. D. Gunstone (ed.), Academic Press, Sheffield, UK (1999), pp. 250 – 267.

    Google Scholar 

  5. G. Saucy and N. Cohen, in: New Synthetic Methodology and Biologically Active Substances. (Proc. 1st Int. Kyoto Conf. New Aspects Org. Chem.), Z. Yoshida (ed.), Elsevier, Amsterdam (1981), pp. 155 – 175.

  6. G. Solladie, in: Studies in Natural Products Chemistry, Vol. 4, Stereoselective Synthesis (Part C), Atta-ut-Rahman (ed.), Elsevier, Amsterdam (1989), pp. 489 – 540.

  7. T. Netscher, Chimia, 50, 563 – 567 (1996).

    CAS  Google Scholar 

  8. V. N. Odinokov, A. Yu. Spivak, and O. V. Knyshenko, Bioorgan. Khim., 33(4), 387 – 404 (2007).

    CAS  Google Scholar 

  9. L. F. Tietze and J. Gorlitzer, Synthesis, 877 – 885 (1997).

  10. L. F. Tietze and J. Gorlitzer, Liebigs Annalen / Recueil, 11, 2221 – 2225 (1997).

    Article  Google Scholar 

  11. L. F. Tietze and J. Gorlitzer, Synthesis, 873 – 878 (1998).

  12. K. Achiwa, T. Suzuki, and F. Mizuguchi, Synlett, 743 – 744 (1996).

  13. E. Mizuguchi, T. Suzuki, and K. Achiwa, Synlett, 929 – 930 (1994).

  14. German Patent 19852903; Chem. Abstr., 132, 321017a (2000).

  15. J. W. Scott, F. T. Bizarro, D. R. Parrish, and G. Saucy, Helv. Chim. Acta, 59(1), 290 – 306 (1976).

    Article  CAS  PubMed  Google Scholar 

  16. S. Takano, Y. Shimazaki, and K. Ogasawara, Heterocycles, 31(5), 917 – 927 (1990).

    Article  CAS  Google Scholar 

  17. N. Cohen, W. F. Eichel, R. J. Lopresti, et al., J. Org. Chem., 41(22), 3505 – 3511 (1976).

    Article  CAS  PubMed  Google Scholar 

  18. Y. Fujita, M. Shiono, K. Ejiri, and K. Saita, Chem. Let., (9), 1399 – 1400 (1985).

  19. J. M. Grisar,M. A. Petty, F. N. Bolkenius, et al., J. Med. Chem., 34(1), 257 – 260 (1991).

    Article  CAS  PubMed  Google Scholar 

  20. V. N. Odinokov, A. Yu. Spivak, G. A. Emel’yanova, et al., Izv. Akad Nauk. Ser. Khim., 11, 2026 – 2033 (2001).

    Google Scholar 

  21. N. Cohen, C. G. Scott, C. Neukom, et al., Helv. Chim. Acta, 64, 1158 – 1173 (1981).

    Article  CAS  Google Scholar 

  22. O. Cachia, J. E. Benna, E. Pedruzzi, et al., J. Biol. Chem., 273, 32,801 – 32,805 (1998).

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Russia, Moscow

    G. D. Gamalevich, A. L. Vlasyuk & É. P. Serebryakov

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  1. G. D. Gamalevich
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  2. A. L. Vlasyuk
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  3. É. P. Serebryakov
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 51, No. 7, pp. 20 – 24, July, 2017.

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Gamalevich, G.D., Vlasyuk, A.L. & Serebryakov, É.P. Chiral Analogs of a-tocopherol. Antioxidant Activity of the (R) and (S) Enantiomers of {2-[6-hydroxy-2,5,7,8-tetramethylchroman-2-yl]ethyl}-trimethylammonium-p-toluenesulfonate Depending on Their Configuration. Pharm Chem J 51, 540–545 (2017). https://doi.org/10.1007/s11094-017-1650-z

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