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Antioxidant Activity of 2-Aminothiazoles Containing a Diterpene Fragment in the Model System of the Liquid-Phase Radical-Chain Oxidation of 1,4-Dioxane

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Abstract

The antioxidant activity of 2-aminothiazoles containing a diterpene fragment in a model system of initiated radical-chain oxidation of 1,4-dioxane was evaluated. The compounds exhibited different inhibitory activities depending on their structure. The effective rate constant of the interaction of substituted 2-aminothiazoles with the 1,4-dioxane peroxyl radical was measured. 2-Aminothiazoles obtained by the chemical transformations of maleopimaric acid N-phenylamide showed higher reactivity with the peroxyl radical.

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REFERENCES

  1. Uchikawa, O., Fukatsu, K., Suno, M., Aono, T., and Doi, T., Chem. Pharm. Bull., 1996, vol. 44, no. 11, p. 2070.

    Article  CAS  Google Scholar 

  2. Kalpana, K.V., Srinivasan, M., and Menon, V.P., Mol. Cell. Biochem., 2008, vol. 314, nos. 1–2, p. 95.

    Article  CAS  Google Scholar 

  3. Kashyap, S.J., Garg, V.K., Sharma, P.K., Kumar, N., Dudhe, R., and Gupta, J.K., Med. Chem. Res., 2012, vol. 21, no. 8, p. 2123.

    Article  CAS  Google Scholar 

  4. De, S., Adhikari, S. Tilak-Jain, J., Menon, V.P., and Devasagayam, T.P.A., Chem.–Biol. Interact., 2008, vol. 173, no. 3, p. 215.

    Article  CAS  Google Scholar 

  5. Karpov, K.A., Pekarevskii, B.V., and Potekhin, V.M., Russ. J. Gen. Chem., 2001, vol. 71, no. 9, p. 1484.

    Article  CAS  Google Scholar 

  6. Yakupova, L.R., Sakhautdinov, I.M., Malikova, R.N., and Safiullin, R.L., Kinet. Catal., 2019, vol. 60, no. 1, p. 21.

    Article  CAS  Google Scholar 

  7. Dikusar, E.A., Bei, M.P., Yuvchenko, A.P., Potkin, V.I., Kozlov, N.G., and Tlegenov, R.E., Khim. Rastit. Syr’ya, 2011, no. 1, p. 105.

  8. Sultanova, R.M. and Sakhautdinov, I.M., Chem. Nat. Compd., 2019, vol. 55, no. 1, p. 47.

    Article  CAS  Google Scholar 

  9. Yakupova, L.R., Ivanova, A.V., Safiullin, R.L., Gimadieva, A.R., Chernyshenko, Yu.N., Mustafin, A.G., and Abdrakhmanov, I.B., Russ. Chem. Bull., 2010, no. 3, p. 517.

  10. Yakupova, L.R., Sakhautdinova, R.A., Pankratyev, E.Y., and Safiullin, R.L., Kinet. Catal., 2012, vol. 53, no. 6, p. 665.

    Article  CAS  Google Scholar 

  11. Sultanova, R.M., Bilalova, L.F., and Mukhamet’yanova, A.F., Bashkirskii Khim. Zh., 2018, vol. 25, no. 2, p. 24.

    Google Scholar 

  12. Moroni, A.F., Makromol. Chem., 1967, vol. 105, no. 6, p. 43.

    Article  CAS  Google Scholar 

  13. Henrici-Olive, G. and Olive, S., Makromol. Chem., 1962, vol. 58, no. 1, p. 188.

    Article  CAS  Google Scholar 

  14. Yakupova, L.R., Proskuryakov, S.G., Zaripov, R.N., Rameev, Sh.R., and Safiullin, R.L., Butlerov. Soobshch., 2011, vol. 28, no. 19, p. 71.

    Google Scholar 

  15. Zhao, Y. and Truhlar, D.G., J. Chem. Phys., 2006, vol. 125, no. 19, p. 194101.

    Article  Google Scholar 

  16. Yakupova, L.R., Safiullin, R.L., Khairullina, V.R., Gerchikov, A.Ya., and Baimuratova, G.R., Kinet. Catal., 2008, vol. 49, no. 3, p. 366.

    Article  CAS  Google Scholar 

  17. Denisov, E.T. and Azatyan, V.V., Ingibirovanie tsepnykh reaktsii (Inhibition of Chain Reactions), Chernogolovka: RAS, 1997.

  18. Tsepalov, V.F., Issledovanie sinteticheskikh i prirodnykh antioksidantov in vitro i in vivo. Sb. nauch. statei (The study of Synthetic and Natural Antioxidants in vitro and in vivo. Collection of Scientific Articles), Moscow: Nauka, 1992, p. 16.

  19. Safiullin, R.L., Zapol’skikh, V.V., Yakupova, L.R., Zaripov, R.N., and Teregulova, A.N., Khim. Fiz., 2001, vol. 20, no. 5, p. 110.

    CAS  Google Scholar 

  20. Denisov, E.T., and Khudyakov, I.G., Chem. Rev., 1987, vol. 87, no. 6, p. 1313.

    Article  CAS  Google Scholar 

  21. Luo, Yu-R., Handbook of Bond Dissociation Energies in Organic Compounds, Boca Raton: CRC, 2003, p. 380.

    Google Scholar 

  22. Denisov, E.T. and Denisova, T.G., Handbook of Antioxidants. Bond Dissociation Energies, Rate Constants, Activation Energies and Enthalpies of Reactions, Boca Raton: CRC, 2017, p. 190.

    Google Scholar 

  23. Valgimigli, L. and Pratt, D.A., Antioxidants in Chemistry and Biology. Encyclopedia of Radicals in Chemistry, Biology and Materials, Chichester: Wiley, 2012, p. 1623.

    Google Scholar 

  24. Yao, G.Y., Ye, M.Y., Huang, R.Z., Li, Y.J., Zhu, Y.T., Pan, Y.M., Liao, Z.X., and Wang, H.S., Bioorg. Med. Chem. Lett., 2013, vol. 23, no. 24, p. 6755.

    Article  CAS  Google Scholar 

  25. Xu, X., Song, Z.-Q., Shang, S.-B., Wang, H.-X., and Rao, X.-P., Acta Crystallogr., Sect. E: Crystallogr. Commun., 2009, vol. 65, no. 10, p. O2443.

    Article  CAS  Google Scholar 

  26. Varlamov, V.T., Safiullin, R.L., and Denisov, E.T., Khim. Fiz., 1983, no. 3, p. 408.

  27. Denisov, E.T. and Afanas’ev, I.B., Oxidation and Antioxidants in Organic Chemistry and Biology, Boca Raton: CRC, 2005, p. 981.

    Book  Google Scholar 

  28. Loshadkin, D., Roginsky, V., and Pliss, E., Int. J. Chem. Kinet., 2002, vol. 34, no. 3, p. 162.

    Article  CAS  Google Scholar 

  29. Pliss, E., Safiullin, R., and Zlotskii, S., Ingibirovannoe okislenie nepredel’nykh soedinenii. Kinetika, mekhanizm, svyaz' struktury s reaktsionnoi sposobnost’yu (Inhibited Oxidation of Unsaturated Compounds. Kinetics, Mechanism, Relationship of Structure and Reactivity), Saarbrucken: Lambert, 2012, p. 140.

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Funding

This study was performed under the R&D plan at the Ufa Institute of Chemistry, Russian Academy of Sciences (state registration nos. АААА-А17-117011910034-8 and АААА-А17-117011910025-6), on the equipment of the Chemistry Multiaccess Center.

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Correspondence to L. R. Yakupova.

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Translated by L. Smolina

Abbreviations: MPA, maleopimaric acid; N-Ph-MPA, maleopimaric acid N-phenylimide; RH, 4-dioxane.

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Yakupova, L.R., Nasibullina, R.A., Shamukaev, V.A. et al. Antioxidant Activity of 2-Aminothiazoles Containing a Diterpene Fragment in the Model System of the Liquid-Phase Radical-Chain Oxidation of 1,4-Dioxane. Kinet Catal 61, 232–237 (2020). https://doi.org/10.1134/S0023158420020123

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