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Synthesis and membrane-protective activity of 2,6-diisobornylphenol derivatives with N- and O-containing fragments at position 4

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Abstract

Two series of new amide derivatives containing 2,6-diisobornylphenol moiety were synthesized based on 3,5-diisobornyl-4-hydroxybenzoic acid and 4-butylaminomethyl-2,6-diisobornylphenol. Toxicity, membrane-protective (MP) and antioxidant (AO) activity of the obtained compounds were evaluated using red blood cells of laboratory mice as the test object. The tests demonstrated the absence of hemolytic activity for all the synthesized derivatives and the presence of high MP and AO activity under conditions of acute H2O2-induced oxidative stress for (3,5-diisobornyl-4-hydroxyphenyl)(morpholino)methanone and N-n-butyl-N-(3,5-diisobornyl-4-hydroxybenzyl)acetamide. A comparison of the data of the newly obtained compounds and those of described earlier 2,6-diisobornylphenol derivatives with N- and O-containing fragments at position 4 (alkoxymethyl, carboxy, and aminomethyl derivatives) led to a conclusion that the most promising for further studies of pharmacological activity are compounds containing methoxycarbonyl, methoxymethyl, ethoxymethyl, morpholinomethyl, di-n-butylaminomethyl, (azepan-1-yl)methyl, or N-acetyl-N-alkylaminomethyl function, which provide low toxicity and high MP and AO activity.

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Authors and Affiliations

  1. Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences, 48 ul. Pervomaiskaya, 167000, Syktyvkar, Russian Federation

    E. V. Buravlev, I. Yu. Chukicheva & A. V. Kutchin

  2. Institute of Biology, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences, 28 ul. Kommunisticheskaya, 167982, Syktyvkar, Russian Federation

    O. G. Shevchenko

Authors
  1. E. V. Buravlev
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  2. I. Yu. Chukicheva
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  3. O. G. Shevchenko
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  4. A. V. Kutchin
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Corresponding author

Correspondence to I. Yu. Chukicheva.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0297—0303, February, 2017.

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Buravlev, E.V., Chukicheva, I.Y., Shevchenko, O.G. et al. Synthesis and membrane-protective activity of 2,6-diisobornylphenol derivatives with N- and O-containing fragments at position 4. Russ Chem Bull 66, 297–303 (2017). https://doi.org/10.1007/s11172-017-1731-x

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  • DOI: https://doi.org/10.1007/s11172-017-1731-x

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