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Synthesis and Antioxidant Activity of New Neomenthyl and Caranyl Thiotriazoles

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Chemistry of Natural Compounds Aims and scope

New neomenthyl and caranyl thiotriazoles were synthesized in up to 80% yields. Studies of the antioxidant and membrane-protective activity of the synthesized compounds in vitro showed that sulfides with a carane moiety were more active than analogs with a neomenthane substituent.

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References

  1. N. Siddiqui, W. Ahsan, M. S. Alam, R. Ali, S. Jain, et al., Int. J. Pharm. Sci. Rev. Res., 8 (1), 161 (2011).

    CAS  Google Scholar 

  2. D. A. Ibrahim, Eur. J. Med. Chem., 44, 2776 (2009).

    Article  CAS  Google Scholar 

  3. I. Ledeti, A. Alexa, V. Bercean, G. Vlase, T. Vlase, L.-M. Suta, and A. Fulias, Int. J. Mol. Sci., 16, 1711 (2015).

    Article  CAS  Google Scholar 

  4. S. I. Khan, A. Badshah, M. Aslam, and M. S. Akhtar, JDDMC, 3, 116 (2012).

    Google Scholar 

  5. A. J. K. Atia, Molecules, 14, 2431 (2009).

    Article  CAS  Google Scholar 

  6. S. Eswaran, A. V. Adhikari, and N. S. Shetty, Eur. J. Med. Chem., 44, 4637 (2009).

    Article  CAS  Google Scholar 

  7. J. Haber, Cas. Lek. Cesk., 140, 596 (2001).

    CAS  PubMed  Google Scholar 

  8. S. Papakonstantinou-Garoufalias, N. Pouli, P. Marakos, and A. Chytyroglou-Ladas, II Farmaco, 57, 973 (2002).

    Article  CAS  Google Scholar 

  9. Y. A. Al-Soud, M. N. Al-Dweri, and N. A. Al-Masoudi, II Farmaco, 59, 775 (2004).

    Article  CAS  Google Scholar 

  10. B. S. Holla, B. Veerendra, M. Shivananda, and B. Poojary, J. Med. Chem., 38, 759 (2003).

    Article  Google Scholar 

  11. R. Lin, P. J. Connolly, S. Huang, S. K. Wetter, Y. Lu, W. V. Murray, S. L. Emanuel, R. H. Gruninger, A. R. Fuentes-Pesquera, and C. A. Rugg, J. Med. Chem., 48, 4208 (2005).

    Article  CAS  Google Scholar 

  12. T. V. Kochikyan, M. A. Samvelyan, E. V. Arutyunyan, V. S. Arutyunyan, A. A. Avetisyan, M. G. Malakyan, L. A. Vardevanyan, and S. A. Badzhinyan, Pharm. Chem. J., 44, 525 (2011).

    Article  CAS  Google Scholar 

  13. S.-F. Barbuceanu, D. C. Ilies, G. Saramet, V. Uivarosi, C. Draghici, and V. Radulescu, Int. J. Mol. Sci., 15, 10908 (2014).

    Article  CAS  Google Scholar 

  14. E. S. Izmestev, D. V. Sudarikov, O. G. Shevchenko, S. A. Rubtsova, and A. V. Kutchin, Bioorg. Khim., 41, 90 (2015).

    CAS  Google Scholar 

  15. E. V. Buravlev, I. Yu. Chukicheva, O. V. Sukrusheva, O. G. Shevchenko, and A. V. Kutchin, Russ. Chem. Bull., Int. Ed., 4, 1406 (2015).

    Article  Google Scholar 

  16. Y. V. Gyrdymova, M. Y. Demakova, O. G. Shevchenko, D. V. Sudarikov, L. L. Frolova, S. A. Rubtsova, and A. V. Kuchin, Chem. Nat. Compd., 53, 895 (2017).

    Article  CAS  Google Scholar 

  17. M. Y. Demakova, D. V. Sudarikov, S. A. Rubtsova, L. L. Frolova, A. V. Popov, P. A. Slepukhin, and A. V. Kuchin, Helv. Chim. Acta, 95, 940 (2012).

    Article  CAS  Google Scholar 

  18. M. Y. Demakova, D. V. Sudarikov, S. A. Rubtsova, P. A. Slepukhin, and A. V. Kuchin, Chem. Nat. Compd., 47, 899 (2012).

    Article  CAS  Google Scholar 

  19. Yu. V. Gyrdymova, D. V. Sudarikov, O. G. Shevchenko, S. A. Rubtsova, P. A. Slepukhin, and A. V. Kutchin, Chem. Biodiversity, 14 (12), e1700296 (2017).

    Article  Google Scholar 

  20. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, and H. Puschmann, J. Appl. Crystallogr., 42, 339 (2009).

    Article  CAS  Google Scholar 

  21. L. Palatinus and G. Chapuis, J. Appl. Crystallogr., 40, 786 (2007).

    Article  CAS  Google Scholar 

  22. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 64, 112 (2008).

  23. H. C. Brown and A. Suzuki, J. Am. Chem. Soc., 89, 1933 (1967).

    Article  CAS  Google Scholar 

  24. A. Banach, J. Scianowski, and P. Ozimek, Phosphorus Sulfur Silicon Relat. Elem., 189, 274 (2014).

    Article  CAS  Google Scholar 

  25. C. I. Acker, R. Brandao, A. R. Rosario, and C. W. Nogueira, Environ. Toxicol. Pharmacol., 28, 280 (2009).

    Article  CAS  Google Scholar 

  26. S. T. Stefanello, A. S. Prestes, T. Ogunmoyole, S. M. Salman, R. S. Schwab, C. R. Brender, L. Dornelles, J. B. T. Rocha, and F. A. A. Soares, Toxicol. in Vitro, 27, 1433 (2013).

    Article  CAS  Google Scholar 

  27. N. A. V. Belle, G. D. Dalmolin, G. Fonini, M. A. Rubim, and J. B. T. Rocha, Brain Res., 1008, 245 (2004).

    Article  CAS  Google Scholar 

  28. R. Chawla, R. Arora, R. Kumar, A. Sharma, J. Prasad, S. Singh, R. Sagar, P. Chaudhary, S. Shukla, G. Kaur, R. K. Sharma, S. C. Puri, K. L. Dhar, G. Handa, V. K. Gupta, and G. N. Qazi, Mol. Cell. Biochem., 273, 193 (2005).

    Article  CAS  Google Scholar 

  29. T. Asakawa and S. Matsushita, Lipids, 15, 137 (1980).

    Article  CAS  Google Scholar 

  30. J. Takebayashi, J. Chen, and A. Tai, in: Advanced Protocols in Oxidative Stress II, Methods in Molecular Biology, D. Armstrong (ed.), Humana Press, Totowa, NJ, 2010, Vol. 594, p 287.

  31. J. M. Berg, J. A. F. Kamp, B. H. Lubin, B. Roelofsen, and F. A. Kuypers, Free Radical Biol. Med., 12 (6), 487 (1992).

    Article  Google Scholar 

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Acknowledgment

The work was financially supported in part by the RFBR (Project 16-53-00171 Bel_a) and the UB, RAS, Molecular Biology Project (No. 18-3-3-17) and used equipment at the Khimiya Common Use Center (CUC), IC, KSC, UB, RAS and the CUC at the IB, KSC, UB, RAS. Animals from the scientific collection of experimental animals of the IB, KSC, UB, RAS were used in the work (http://www.ckp-rf.ru/usu/471933/).

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Correspondence to D. V. Sudarikov.

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Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2018, pp. 750–754.

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Gyrdymova, Y.V., Sudarikov, D.V., Shevchenko, O.G. et al. Synthesis and Antioxidant Activity of New Neomenthyl and Caranyl Thiotriazoles. Chem Nat Compd 54, 883–888 (2018). https://doi.org/10.1007/s10600-018-2504-y

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  • DOI: https://doi.org/10.1007/s10600-018-2504-y

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