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5-Hydroxy-2,3-dihydrobenzofuran-derived polyfunctional antioxidants

1. Synthesis of 2-dodecylthiomethyl-5-hydroxy-2,3-dihydrobenzofurans

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Abstract

2-Dodecylthiomethyl-5-hydroxy-2,3-dihydrobenzofurans, new sulfur-containing analogs of tocopherols, were synthesized based on methylphenols through the intermediate preparation of 4-alkoxy-2-allylphenols and then 5-alkoxy-2-iodomethyl-2,3-dihydrobenzofurans.

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References

  1. E. B. Men´shchikova, V. Z. Lankin, N. V. Kandalintseva, Fenol´nye antioksidanty v biologii i meditsine: Stroenie, svoistva, mekhanizmy deistviya [Phenol Antioxidants in Biology and Medicine: Structure, Properties, Mechanisms of Action], LAP LAMBERT Academic Publishing, Saarbrücken, 2012, 488 pp. (in Russian).

    Google Scholar 

  2. B. Halliwell, J. M. C. Gutteridge, Free Radicals in Biology and Medicine: Fifth Edition, Oxford University Press, Oxford, 2015, 1224 pp.

    Book  Google Scholar 

  3. H. A. Zahalka, B. Robillard, L. Hughes, J. Lusztyk, G. W. Burton, E. G. Janzen, Y. Kotake, K. U. Ingold, J. Org. Chem., 1988, 53, 3739.

    Article  CAS  Google Scholar 

  4. J. Malmström, M. Jonsson, I. A. Cotgreave, L. Hammarström, M. Sjödin, L. Engman, J. Am. Chem. Soc., 2001, 123, 3434.

    Article  Google Scholar 

  5. J. Poon, V. P. Singh, J. Yan, L. Engman, Chemistry — A European Journal, 2015, 21, 2447.

    Article  CAS  Google Scholar 

  6. T. Tanaka, R. Kusano, I. Kouno, Bioorg. Med. Chem. Lett., 1998, 8, 1801.

    Article  CAS  Google Scholar 

  7. S. E. Yagunov, S. V. Kholshin, N. V. Kandalintseva, A. E. Prosenko, Russ. Chem. Bull., 2013, 62, 1395.

    Article  CAS  Google Scholar 

  8. A. S. Oleynik, Ph. D. (Chem.), Novosibirsk State Pedagogical University, Novosibirsk, 2009, 155 pp. (in Russian).

    Google Scholar 

  9. R. Amorati, M. G. Fumo, S. Menichetti, V. Mugnaini, G. F. Pedulli, J. Org. Chem., 2006, 71, 6325.

    Article  CAS  Google Scholar 

  10. WO Pat. 2006129318 (A2); Chem. Abstrs., 2006, 146, 62574.

  11. E. A. Kemeleva, E. A Vasyunina, O. I. Sinitsina, A. S. Khomchenko, M. A. Gross, N. V. Kandalintseva, A. E. Prosenko, G. A. Nevinskii, Russ. J. Bioorg. Chem., 2008, 34, 499.

    Article  CAS  Google Scholar 

  12. S. E. Yagunov, S. V. Kholshin, N. V. Kandalintseva, Vestnik Novosibirskogo gosudarstvennogo pedagogicheskogo universiteta [Bull. Novosibirsk State Pedagogical Univ.], 2013, 5, 5 (in Russian).

    Google Scholar 

  13. A. Closse, W. Haefliger, D. Hauser, H. U. Gubler, B. Dewald, M. Baggiolini, J. Med. Chem., 1981, 24, 1465.

    Article  CAS  Google Scholar 

  14. D. E. Nichols, S. E. Snyder, R. Oberlender, M. P. Johnson, X. Huang, J. Med. Chem., 1991, 34, 276.

    Article  CAS  Google Scholar 

  15. S. R. Waldman, A. P. Monte, A. Bracey, D. E. Nichols, Tetrahedron Lett., 1996, 37, 7889.

    Article  CAS  Google Scholar 

  16. W. L. F. Armarego, C. L. L. Chai, Purification of Laboratory Chemicals, Elsevier, 2013, 1002.

    Google Scholar 

  17. US Pat. 4009210; Chem. Abstrs, 1977, 86, 55159.

  18. US Pat. 5840997; Chem. Abstrs, 1998, 129, 343330.

  19. A. S. Oleynik, Т. S. Kuprina, N. Yu. Pevneva, A. F. Markov, N. V. Kandalintseva, A. E. Prosenko, I. A. Grigor´ev, Russ. Chem. Bull., 2007, 56, 1135.

    Article  CAS  Google Scholar 

  20. Yu. N. Trubnikova, S. E. Yagunov, A. S. Oleynik, N. V. Kandalintseva, A. E. Prosenko, Khimiya v interesakh ustoichivogo razvitiya [Chem. Sustain. Development], 2011, 19, 685 (in Russian).

    CAS  Google Scholar 

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Authors and Affiliations

  1. Novosibirsk State Pedagogical University, 28 ul. Vilyuiskaya, 630126, Novosibirsk, Russian Federation

    S. E. Yagunov, S. V. Kholshin, N. V. Kandalintseva & A. E. Prosenko

  2. Novosibirsk Institute of Antioxidants, 54a ul. Krasnyi prospekt, 630091, Novosibirsk, Russian Federation

    N. V. Kandalintseva & A. E. Prosenko

Authors
  1. S. E. Yagunov
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  2. S. V. Kholshin
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  3. N. V. Kandalintseva
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  4. A. E. Prosenko
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Corresponding author

Correspondence to S. E. Yagunov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1024—1029, June, 2017.

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Yagunov, S.E., Kholshin, S.V., Kandalintseva, N.V. et al. 5-Hydroxy-2,3-dihydrobenzofuran-derived polyfunctional antioxidants. Russ Chem Bull 66, 1024–1029 (2017). https://doi.org/10.1007/s11172-017-1850-4

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  • DOI: https://doi.org/10.1007/s11172-017-1850-4

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