Skip to main content
Log in

2-Hydroxy-3-isobornyl-5-methylbenzaldehyde derivatives: synthesis and antioxidant activity in vitro

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A series of N- and O-containing derivatives based on 2-hydroxy-3-isobornyl-5-methylbenzaldehyde was synthesized. A comparative evaluation of their radical scavenging activity tested with diphenylpicrylhydrazyl, antioxidant activity estimated on a substrate containing animal lipids, Fe2+-chelating ability using the FerroZine™ Iron Reagent, cytotoxicity, and also antioxidant and membrane-protective properties towards mammalian red blood cells was performed. The listed properties of the synthesized derivatives are essentially determined by the structure of the substituent introduced at the ortho-position. Compounds exhibiting a high activity in both cellular and non-cellular models were revealed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. M. Cirri, P. Mura, P. Corvi Mora, Int. J. Pharm., 2007, 340, 84.

    Article  CAS  PubMed  Google Scholar 

  2. O. I. Kiselev, Khimiopreparaty i khimioterapiya grippa [Chemotherapeutic Agents and Chemotherapy of Influenza], Rostok, St. Petersburg, 2012, 272 pp. (in Russian).

    Google Scholar 

  3. E. V. Buravlev, I. Y. Chukicheva, K. Y. Suponitsky, Y. B. Vikha rev, V. V. Grishko, A. V. Kutchin, Lett. Org. Chem., 2011, 8, 301.

    Article  CAS  Google Scholar 

  4. M. B. Plotnikov, V. I. Smol´yakova, I. S. Ivanov, A. V. Kuchin, I. J. Chukicheva, E. V. Buravlev, E. A. Krasnov, Pharm. Chem. J., 2011, 44, 530.

    Article  CAS  Google Scholar 

  5. O. G. Shevchenko, S. N. Plyusnina, E. V. Buravlev, I. Yu. Chukicheva, I. V. Fedorova, O. V. Shchukina, A. V. Kutchin, Russ. Chem. Bull., 2017, 66, 1881.

    Article  CAS  Google Scholar 

  6. A. Berkessel, M. R. Vennemann, J. Lex, Eur. J. Org. Chem., 2002, 2800.

    Google Scholar 

  7. I. I. Oleinik, V. E. Romanov, I. V. Oleinik, S. S. Ivanchev, Russ. J. Org. Chem., 2008, 44, 107.

    Article  CAS  Google Scholar 

  8. E. V. Buravlev, I. Y. Chukicheva, A. V. Kutchin, Synth. Commun., 2009, 39, 3639.

    Article  CAS  Google Scholar 

  9. E. V. Buravlev, I. Yu. Chukicheva, F. M. Dolgushin, A. V. Kutchin, Russ. J. Org. Chem., 2010, 46, 649.

    Article  CAS  Google Scholar 

  10. K. Brodowska, E. Łodyga-Chruścińska, Chemik, 2014, 68, 129.

    CAS  Google Scholar 

  11. A. H. Vetter, A. Berkessel, Tetrahedron Lett., 1998, 39, 1741.

    Article  CAS  Google Scholar 

  12. I. A. Dvornikova, E. V. Buravlev, K. Yu. Suponitskii, I. Yu. Chu kicheva, A. V. Kutchin, Russ. J. Org. Chem., 2015, 51, 480.

    Article  CAS  Google Scholar 

  13. M. H. Sarvari, Synthesis, 2005, 787.

    Google Scholar 

  14. P. Mestichelli, M. J. Scott, W. R. J. D. Galloway, J. Selwyn, J. S. Parker, D. R. Spring, Org. Lett., 2013, 15, 5448.

    Article  CAS  PubMed  Google Scholar 

  15. T. R. Forder, M. D. Jones, New. J. Chem., 2015, 39, 1974.

    Article  CAS  Google Scholar 

  16. V. B. Vol´eva, N. L. Komissarova, I. S. Belostotskaya, E. A. Grishina, V. V. Ershov, Russ. Chem. Bull., 1991, 40, 2088.

    Article  Google Scholar 

  17. M. Wąsiń ska, A. Korczewska, M. Giurg, J. Skarżewski, Synth. Commun., 2015, 45, 143.

    Article  CAS  Google Scholar 

  18. E. V. Buravlev, I. Yu. Chukicheva, M. A. Elfimova, K. Yu. Suponitskii, A. V. Kutchin, Russ. J. Org. Chem., 2015, 51, 623.

    Article  CAS  Google Scholar 

  19. D. V. Belykh, E. V. Buravlev, I. Yu. Chukicheva, I. S. Tarabukina, O. G. Shevchenko, S. N. Plyusnina, A. V. Kutchin, Russ. J. Bioorg. Chem., 2012, 38, 558.

    Article  CAS  Google Scholar 

  20. E. V. Buravlev, O. G. Shevchenko, I. Y. Chukicheva, A. V. Kut chin, Chem. Pap., 2018, 72, 201.

    Article  CAS  Google Scholar 

  21. E. V. Buravlev, O. G. Shevchenko, A. V. Kutchin, Bioorg. Med. Chem. Lett., 2015, 25, 826.

    Article  CAS  PubMed  Google Scholar 

  22. E. V. Buravlev, O. G. Shevchenko, A. A. Anisimov, K. Yu. Suponitsky, Eur. J. Med. Chem., 2018, 152, 10.

    Article  CAS  PubMed  Google Scholar 

  23. L. J. Kitchen, J. Am. Chem. Soc., 1948, 70, 3608.

    Article  CAS  PubMed  Google Scholar 

  24. E. V. Buravlev, I. Yu. Chukicheva, K. Yu. Suponitskii, A. V. Kuchin, Russ. J. Gen. Chem., 2008, 78, 1411.

    Article  CAS  Google Scholar 

  25. L. F. Fieser, M. Fieser, Reagents for Organic Synthesis, Wiley, New York, 1967, 1457 pp.

    Google Scholar 

  26. K. Sevgi, B. Tepe, C. Sarikurkcu, Food Chem. Toxicol., 2015, 77, 12.

    Article  CAS  PubMed  Google Scholar 

  27. U. Sukatta, M. Takenaka, H. Ono, H. Okadome, I. Sotome, K. Nanayama, W. Thanapase, S. Isobe, Biosci. Biotechnol. Biochem., 2013, 77, 984.

    Article  CAS  PubMed  Google Scholar 

  28. J. Lin, Y. Gao, H. Li, L. Zhang, X. Li, Adv. Pharmaceut. Bull., 2014, 4, 147.

    Google Scholar 

  29. C. I. Acker, R. Brandao, A. R. Rosario, C. W. Nogueira, Environ. Toxicol. Pharmacol., 2009, 28, 280.

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  32. 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, G. N. Qazi, Mol. Cell. Biochem., 2005, 273, 193.

    Article  CAS  PubMed  Google Scholar 

  33. T. Asakawa, S. Matsushita, Lipids, 1980, 15, 137.

    Article  CAS  Google Scholar 

  34. J. Takebayashi, J. Chen, A. A. Tai, Methods Mol. Biol., 2010, 594, 287.

    Article  CAS  PubMed  Google Scholar 

  35. J. J. M. Van den Berg, J. A. F. Opden Kamp, B. H. Lubin, B. Roelofsen, F. A. Kuypers, Free Radical Biol. Med., 1992, 12, 487.

    Article  CAS  Google Scholar 

  36. E. Nagababu, J. M. Rifkind, Biochem. Biophys. Res. Commun., 1998, 247, 592.

    Article  CAS  PubMed  Google Scholar 

  37. E. Nagababu, M. E. Fabry, R. L. Nagel, J. M. Rifkind, Blood Cells Mol. Dis., 2008, 41, 60.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. V. Buravlev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0079–0085, January, 2019.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Buravlev, E.V., Shevchenko, O.G. 2-Hydroxy-3-isobornyl-5-methylbenzaldehyde derivatives: synthesis and antioxidant activity in vitro. Russ Chem Bull 68, 79–85 (2019). https://doi.org/10.1007/s11172-019-2419-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-019-2419-1

Key words

Navigation