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A Convenient Synthesis of Retinal Derivatives with Modified Trimethylcyclohexene Ring

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Abstract

A method of simultaneous one-stage synthesis of three retinal derivatives (5,6-dioxo-5,6-seco-, 5,6-dihydro-5,6-epoxy-, and 4-oxoretinal) was proposed, with the yield of the first derivative being ∼50%. These compounds are useful tools for studying the antitumor activity of retinoids, the reconstituted bacteriorhodopsin analogues with changed parameters of photocycle, and the reactivity of retinal derivatives in the processes of oxidation by molecular oxygen.

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REFERENCES

  1. The Retinoids, vols. 1 and 2, Sporn, M.B., Roberts, A.B., and Goodman, D.S., Eds., Orlando: Academic, 1984.

    Google Scholar 

  2. The Retinoids: Biology, Chemistry, and Medicine, vols.1-3, Sporn, M.B., Roberts, A.B., and Goodman, D.S., Eds., New York: Raven, 1994.

    Google Scholar 

  3. Chemistry and Biology of Synthetic Retinoids, Dawson, M.I. and Okamura, W.H., Eds., Boca Raton: CRC, 1990.

    Google Scholar 

  4. Retinoids. Advances in Basic Research and Therapy, Orfanos, C.E., Braun-Falco, O., Farbe, O., Grupper, C., Polano, M.K., and Schuppli, R., Eds., Berlin: Springer, 1981.

    Google Scholar 

  5. Mitsner, B.I., Khodonov, A.A., Zvonkova, E.N., and Evstigneeva, R.P., Bioorg. Khim., 1986, vol. 12, pp. 5-53.

    Google Scholar 

  6. Khodonov, A.A., Eremin, S.V., Lokshin, J.L., Shvets,V.I., Demina, O.V., Khitrina, L.V., and Kaulen, A.D., Bioorg. Khim., 1996, vol. 22, pp. 745-776.

    Google Scholar 

  7. Nakanishi, K. and Crouch, R.K., Israel J. Chem., 1995, vol. 35, pp. 253-272.

    Google Scholar 

  8. Henbest, H.B., Jones, E.R.H., and Owen, T.C., J. Chem. Soc., 1957, pp. 4902-4912.

  9. Sokolova, N.A., Mitsner, B.I., and Zakis, V.I., Bioorg. Khim., 1979, vol. 5, pp. 1053-1058.

    Google Scholar 

  10. Serebryanyi, V.A., Mitsner, B.I., Zakis, V.I., and Tsetlin,V.I., Bioorg. Khim., 1981, vol. 7, pp. 1731-1733.

    Google Scholar 

  11. Beischel, C.J., Mani, V., Govindjee, R., Ebrey, T.G., Knaff, D.R., and Crouch, R.K., Photochem. Photobiol., 1991, vol. 54, pp. 977-983.

    Google Scholar 

  12. Colmenares, L.U. and Liu, R.S.H., Tetrahedron Lett., 1991, vol. 32, pp. 1933-1936.

    Google Scholar 

  13. Schwieter, U., Arnold, W., Oberhansli, W.E., Rigassi, N., and Vetter, W., Helv. Chim. Acta, 1971, vol. 54, pp.2447-2459.

    Google Scholar 

  14. Oyler, A.R., Motto, M.G., Naldi, R.E., Facchine, K.L., Hamburg, P.F., Burinsky, D.J., Dunphy, R., and Cotter, M.L., Tetrahedron, 1989, vol. 45, pp. 7679-7694.

    Google Scholar 

  15. John, K.V., Laksmann, M.R., and Cama, H.R., Biochem. J., 1967, vol. 103, pp. 543-549.

    Google Scholar 

  16. Jungalwala, F.B. and Cama, H.R., Biochem. J., 1965, vol. 95, pp. 17-26.

    Google Scholar 

  17. Dawson, M.I. and Hobbs, P.D., The Retinoids: Biology, Chemistry, and Medicine, Sporn, M.B., Roberts, A.B., and Goodman, D.S., Eds., New York: Raven, 1994, vol.1, pp. 5-178.

    Google Scholar 

  18. Dawson, M.I., Hobbs, P.D., Chan, R.L.-S., and Chao, W.-R., J. Med. Chem., 1981, vol. 24, pp. 1214-1223.

    Google Scholar 

  19. Zhidkova, T.A., Bekker, A.R., Vakulova, L.A., and Samokhvalov, G.I., Zh. Org. Khim., 1984, vol. 20, pp.1678-1683.

    Google Scholar 

  20. Aig, E., Focella, A., Parrish, D.R., Rosenberger, M., Scott, J.W., and Zenchoff, G.B., Synth. Commun., 1987, vol. 17, pp. 419-429.

    Google Scholar 

  21. Rosenberger, M., J. Org. Chem., 1982, vol. 47, pp.1698-1701.

    Google Scholar 

  22. Rosenberger, M. and Neucom, C., J. Org. Chem., 1982, vol. 47, pp. 1779-1782.

    Google Scholar 

  23. Rosenberger, M. and Neucom, C., J. Org. Chem., 1982, vol. 47, pp. 1782-1785.

    Google Scholar 

  24. Barua, A.B. and Ghosh, M.C., Tetrahedron Lett., 1972, pp. 1823-1825.

  25. Acton, N. and Brossi, A., Helv. Chim. Acta, 1980, vol.63, pp. 1391-1395.

    Google Scholar 

  26. Singh, A.K., Synth. Commun., 1983, vol. 13, pp. 919-925.

    Google Scholar 

  27. Shealy, Y.F., Hosmer, C.A., and Riordan, J.M., Synthesis, 1993, pp. 1095-1098.

  28. Khodonov, A.A., Synthetic Approach to Studying the Structure-Activity Relation in Retinoid-Protein Complexes, Bacteriorhodopsin and Nuclear Receptors of Retinoic Acid, Doctoral (Chem.) Dissertation, Moscow: Lomonosov State Academy of Fine Chemical Technology, Moscow, 1997.

    Google Scholar 

  29. Barua, A.B. and Olson, J.A., J. Lipid Res., 1984, vol. 25, pp. 304-309.

    Google Scholar 

  30. Williams, T.C. and Mani, V., Biochemistry, 1991, vol. 30, pp. 2976-2988.

    Google Scholar 

  31. Finkel'shtein, E.I. and Krasnokutskaya, I.S., J. Phys. Org. Chem., 1996, vol. 9, pp. 411-418.

    Google Scholar 

  32. Finkel'shtein, E.I., Krasnokutskaya, I.S., and Vakulova,L.A., J. Mol. Struct., 1999, vol. 480/481, pp. 569-571.

    Google Scholar 

  33. Corey, E.J., Gilman, N.V., and Ganem, B.E., J. Am. Chem. Soc., 1968, vol. 90, pp. 5616-5619.

    Google Scholar 

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Authors and Affiliations

  1. Lomonosov State Academy of Fine Chemical Technology, pr. Vernadskogo 86, Moscow, 119571, Russia

    E. V. Mironova, S. V. Leont'eva, S. V. Shevyakov, S. G. Alexeeva, V. I. Shvets, I. S. Krasnokutskaya, E. I. Finkel'shtein & A. A. Khodonov

  2. Russian Academy of Sciences, Emanuel Institute of Biochemical Physics, Moscow

    O. V. Demina

Authors
  1. E. V. Mironova
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  2. S. V. Leont'eva
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  3. S. V. Shevyakov
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  4. S. G. Alexeeva
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  5. V. I. Shvets
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  6. O. V. Demina
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  7. I. S. Krasnokutskaya
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  8. E. I. Finkel'shtein
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  9. A. A. Khodonov
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Mironova, E.V., Leont'eva, S.V., Shevyakov, S.V. et al. A Convenient Synthesis of Retinal Derivatives with Modified Trimethylcyclohexene Ring. Russian Journal of Bioorganic Chemistry 28, 487–494 (2002). https://doi.org/10.1023/A:1021245616117

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