Skip to main content
SpringerLink
Log in

Synthesis of new efficient and selective carboxylesterase inhibitors based on adamantyl and citronellyl 4,4,4-trifluoro-2-arylhydrazonylidene-3-oxobutanoates

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

Abstract

A series of new adamantyl and citronellyl 4,4,4-trifluoro-2-arylhydrazinylidene-3-oxo-butanoates was synthesized. The synthesized compounds in nanomolar concentrations selectively inhibit carboxylesterase, while their activity is independent of the nature and position of the substituent in the aryl fragment, which is consistent with the molecular docking results.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. E. V. Shchegolkov, Y. V. Burgart, O. G. Khudina, V. I. Saloutin, O. N. Chupakhin, Russ. Chem. Rev., 2010, 79, 31; DOI: https://doi.org/10.1070/RC2010v079n01ABEH004048.

    Article  CAS  Google Scholar 

  2. L. V. Politanskaya, G. A. Selivanova, E. V. Panteleeva, E. V. Tretyakov, V. E. Platonov, P. V. Nikul’shin, A. S. Vinogradov, Y. V. Zonov, V. M. Karpov, T. V. Mezhenkova, A. V. Vasilyev, A. B. Koldobskii, O. S. Shilova, S. M. Morozova, Ya. V. Burgart, E. V. Shchegolkov, V. I. Saloutin, V. B. Sokolov, A. Yu. Aksinenko, V. G. Nenajdenko, M. Yu. Moskalik, V. V. Astakhova, B. A. Shainyan, A. A. Tabolin, S. L. Ioffe, V. M. Muzalevskiy, E. S. Balenkova, A. V. Shastin, A. A. Tyutyunov, V. E. Boiko, S. M. Igumnov, A. D. Dilman, N. Yu. Adonin, V._V. Bardin, S. M. Masoud, D. V. Vorobyeva, S. N. Osipov, E. V. Nosova, G. N. Lipunova, V. N. Charushin, D. O. Prima, A. G. Makarov, A. V. Zibarev, B. A. Trofimov, L. N. Sobenina, K. V. Belyaeva, V. Ya. Sosnovskikh, D. L. Obydennov, S. A. Usachev, Russ. Chem. Rev., 2019, 88, 425; DOI: https://doi.org/10.1070/RCR4871.

    Article  CAS  Google Scholar 

  3. C. A. M. Fraga, E. J. Barreiro, Curr. Med. Chem., 2006, 13, 167; DOI: https://doi.org/10.2174/092986706775197881.

    Article  CAS  PubMed  Google Scholar 

  4. C. Isanbor, D. O’Hagan, J. Fluorine Chem., 2006, 127, 303; DOI: https://doi.org/10.1016/j.jfluchem.2006.01.011.

    Article  CAS  Google Scholar 

  5. K. L. Kirk, J. Fluorine Chem., 2006, 127, 1013; DOI: https://doi.org/10.1016/j.jfluchem.2006.06.007.

    Article  CAS  Google Scholar 

  6. J.-P. Bégué, D. Bonnet-Delpon, J. Fluorine Chem., 2006, 127, 992; DOI: https://doi.org/10.1016/j.jfluchem.2006.05.006.

    Article  CAS  Google Scholar 

  7. D. O’Hagan, J. Fluorine Chem., 2010, 131, 1071; DOI: https://doi.org/10.1016/j.jfluchem.2010.03.003.

    Article  CAS  Google Scholar 

  8. W. K. Hagmann, J. Med. Chem., 2008, 51, 4359; DOI: https://doi.org/10.1021/jm800219f.

    Article  CAS  PubMed  Google Scholar 

  9. I. A. Al-Suwaidan, N. I. Abdel-Aziz, A. S. El-Azab, M. A.-A. El-Sayed, A. M. Alanazi, M. B. El-Ashmawy, A. A.-M. Abdel-Aziz, J. Enzyme Inhib. Med. Chem., 2015, 30, 679; DOI: https://doi.org/10.3109/14756366.2014.960863.

    Article  CAS  PubMed  Google Scholar 

  10. M. A.-A. El-Sayed, N. I. Abdel-Aziz, A. A.-M. Abdel-Aziz, A. S. El-Azab, Y. A. Asiri, K. E. H. ElTahir, Bioorg. Med. Chem., 2011, 19, 3416; DOI: https://doi.org/10.1016/j.bmc.2011.04.027.

    Article  CAS  PubMed  Google Scholar 

  11. V. Kumar, G. K. Gupta, K. Kaur, R. Singh, Med. Chem. Res., 2013, 22, 5890; DOI: https://doi.org/10.1007/s00044-013-0566-8.

    Article  CAS  Google Scholar 

  12. Pat. CN 104478760; Chem. Abstrs, 2015, 162, 514150.

  13. Pat. CN 107372496; Chem. Abstrs, 2017, 168, 42904.

  14. P. Bandyopadhyay, L. Guha, T. Seenivasagan, M. Sathe, P. Sharma, B. D. Parashar, M. P. Kaushik, Bioorg. Med. Chem. Lett., 2011, 21, 794; DOI: https://doi.org/10.1016/j.bmcl.2010.11.101.

    Article  CAS  PubMed  Google Scholar 

  15. S. K. Agrawal, S. Tikar, R. Yadav, A. K. Halve, M. Sathe, New J. Chem., 2014, 38, 4527; DOI: https://doi.org/10.1039/C4NJ00647J.

    Article  CAS  Google Scholar 

  16. O. G. Khudina, G. F. Makhaeva, N. A. Elkina, N. P. Boltneva, O. G. Serebryakova, E. V. Shchegolkov, E. V. Rudakova, S. V. Lushchekina, Y. V. Burgart, S. O. Bachurin, R. J. Richardson, V. I. Saloutin, Bioorg. Med. Chem. Lett., 2019, 29, 126716. DOI: https://doi.org/10.1016/j.bmcl.2019.126716.

    Article  CAS  PubMed  Google Scholar 

  17. N. P. Boltneva, G. F. Makhaeva, N. V. Kovaleva, S. V. Lushchekina, Ya. V. Burgart, E. V. Shchegol’kov, V. I. Saloutin, O. N. Chupakhin, Dokl. Biochem. Biophys., 2015, 465, 381; DOI: https://doi.org/10.1134/S1607672915060101.

    Article  CAS  PubMed  Google Scholar 

  18. G. F. Makhaeva, E. V. Rudakova, N. V. Kovaleva, S. V. Lushchekina, N. P. Boltneva, A. N. Proshin, E. V. Shchegolkov, Ya. V. Burgart, V. I. Saloutin, Russ. Chem. Bull., 2019, 68, 967; DOI: https://doi.org/10.1007/s11172-019-2507-2.

    Article  CAS  Google Scholar 

  19. Pat. RF 2574291; Chem. Abstrs, 2016, 164, 225608 (in Russian).

  20. N. P. Boltneva, G. F. Makhaeva, E. V. Shchegol’kov, Ya. V. Burgart, V. I. Saloutin, Biomed. Chem. Res. Methods, 2018, 1, e00026; DOI: https://doi.org/10.18097/BMCRM00026.

    Article  Google Scholar 

  21. M. K. Ross, J. A. Crow, J. Biochem. Mol. Toxicol., 2007, 21, 187; DOI: https://doi.org/10.1002/jbt.20178.

    Article  CAS  PubMed  Google Scholar 

  22. T. Imai, K. Ohura, Curr. Drug Metab., 2010, 11, 793; DOI: https://doi.org/10.2174/138920010794328904.

    Article  CAS  PubMed  Google Scholar 

  23. P. Potter, R. Wadkins, Curr. Med. Chem., 2006, 13, 1045; DOI: https://doi.org/10.2174/092986706776360969.

    Article  CAS  PubMed  Google Scholar 

  24. M. J. Hatfield, P. M. Potter, Expert Opin. Ther. Pat., 2011, 21, 1159; DOI: https://doi.org/10.1517/13543776.2011.586339.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. S. C. Laizure, V. Herring, Z. Hu, K. Witbrodt, R. B. Parker, Pharmacotherapy, 2013, 33, 210; DOI: https://doi.org/10.1002/phar.1194.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. D. Wang, L. Zou, Q. Jin, J. Hou, G. Ge, L. Yang, Acta Pharm. Sin. B, 2018, 8, 699; DOI: https://doi.org/10.1016/j.apsb.2018.05.005.

    Article  PubMed  PubMed Central  Google Scholar 

  27. E. V. Shchegol’kov, G. F. Makhaeva, N. P. Boltneva, S. V. Lushchekina, O. G. Serebryakova, E. V. Rudakova, N. V. Kovaleva, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin, S. O. Bachurin, R. J. Richardson, Bioorg. Med. Chem., 2017, 25, 3997; DOI: https://doi.org/10.1016/j.bmc.2017.05.045.

    Article  PubMed  CAS  Google Scholar 

  28. G. F. Makhaeva, N. A. Elkina, E. V. Shchegolkov, N. P. Boltneva, S. V. Lushchekina, O. G. Serebryakova, E. V. Rudakova, N. V. Kovaleva, E. V. Radchenko, V. A. Palyulin, Ya. V. Burgart, V. I. Saloutin, S. O. Bachurin, R. J. Richardson, Bioorg. Chem., 2019, 91, 103097; DOI: https://doi.org/10.1016/j.bioorg.2019.103097.

    Article  CAS  PubMed  Google Scholar 

  29. L. Di, Curr. Drug Metab., 2019, 20, 91; DOI: https://doi.org/10.2174/1389200219666180821094502.

    Article  CAS  PubMed  Google Scholar 

  30. T. Imai, M. Hosokawa, J. Pestic. Sci., 2010, 35, 229; DOI: https://doi.org/10.1584/jpestics.R10-03.

    Article  CAS  Google Scholar 

  31. S. Jana, S. Mandlekar, P. Marathe, Curr. Med. Chem., 2010, 17, 3874; DOI: https://doi.org/10.2174/092986710793205426.

    Article  CAS  PubMed  Google Scholar 

  32. M. R. Redinbo, P. M. Potter, Drug Discov. Today, 2005, 10, 313; DOI: https://doi.org/10.1016/S1359-6446(05)03383-0.

    Article  CAS  PubMed  Google Scholar 

  33. S. Mukherjee, M. Choi, J. W. Yun, Appl. Physiol. Nutr. Metab., 2019, 44, 1089; DOI: https://doi.org/10.1139/apnm-2018-0814.

    Article  CAS  PubMed  Google Scholar 

  34. J. Lian, R. Nelson, R. Lehner, Protein Cell., 2018, 9, 178; DOI: https://doi.org/10.1007/s13238-017-0437-z.

    Article  CAS  PubMed  Google Scholar 

  35. Y. Xu, C. Zhang, W. He, D. Liu, Eur. J. Drug Metab. Pharmacokinet., 2016, 41, 321; DOI: https://doi.org/10.1007/s13318-016-0326-5.

    Article  CAS  PubMed  Google Scholar 

  36. M. K. Ross, T. M. Streit, K. L. Herring, S. Xie, J. Pestic. Sci., 2010, 35, 257; DOI: https://doi.org/10.1584/jpestics.R10-07.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. Y.-J. Liu, S.-Y. Li, J. Hou, Y.-F. Liu, D.-D. Wang, Y.-S. Jiang, G.-Bo Ge, X.-M. Liang, L. Yang, Fitoterapia, 2016, 115, 57; DOI: https://doi.org/10.1016/j.fitote.2016.09.022.

    Article  CAS  PubMed  Google Scholar 

  38. D.-D. Wang, L.-W. Zou, Q. Jin, J. Hou, G.-B. Ge, L. Yang, Fitoterapia, 2017, 117, 84; DOI: https://doi.org/10.1016/j.fitote.2017.01.010.

    Article  CAS  PubMed  Google Scholar 

  39. G. F. Makhaeva, E. V. Radchenko, V. A. Palyulin, E. V. Rudakova, A. Y. Aksinenko, V. B. Sokolov, N. S. Zefirov, R. J. Richardson, Chem. Biol. Interact., 2013, 203, 231; DOI: https://doi.org/10.1016/j.cbi.2012.10.012.

    Article  CAS  PubMed  Google Scholar 

  40. G. F. Makhaeva, E. V. Rudakova, O. G. Serebryakova, A. Y. Aksinenko, S. V. Lushchekina, S. O. Bachurin, R. J. Richardson, Chem. Biol. Interact., 2016, 259, 332; DOI: https://doi.org/10.1016/j.cbi.2016.05.002.

    Article  CAS  PubMed  Google Scholar 

  41. A. A. Szćkàcs, B. Bordàs, B. D. Hammock, in Rational Approaches to Structure, Activity, and Ecotoxicology of Agro-chemicals, Eds W. Draber, T. Fujita, CRC Press, Boca Raton, 1992, pp. 219–249.

  42. O. G. Khudina, E. V. Shchegol’kov, Ya. V. Burgart, M. I. Kodess, O. N. Kazheva, A. N. Chekhlov, G. V. Shilov, O. A. Dyachenko, V. I. Saloutin, O. N. Chupakhin, J. Fluorine Chem., 2005, 126, 1230; DOI: https://doi.org/10.1016/j.jfluchem.2005.06.001.

    Article  CAS  Google Scholar 

  43. S. H. Sterri, B. A. Johnsen, F. Fonnum, Biochem. Pharmacol., 1985, 34, 2779; DOI: https://doi.org/10.1016/0006-2952(85)90579-9.

    Article  CAS  PubMed  Google Scholar 

  44. G. L. Ellman, K. D. Courtney, V. Andres, R. M. Featherstone, Biochem. Pharmacol., 1961, 7, 88; DOI: https://doi.org/10.1016/0006-2952(61)90145-9.

    Article  CAS  PubMed  Google Scholar 

  45. M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem., 1993, 14, 1347; DOI: https://doi.org/10.1002/jcc.540141112.

    Article  CAS  Google Scholar 

  46. R. S. Mulliken, J. Chem. Phys., 1955, 23, 1833; DOI: https://doi.org/10.1063/1.1740588.

    Article  CAS  Google Scholar 

  47. S. Bencharit, C. C. Edwards, C. L. Morton, E. L. Howard-Williams, P. Kuhn, P. M. Potter, M. R. Redinbo, J. Mol. Biol., 2006, 363, 201; DOI: https://doi.org/10.1016/j.jmb.2006.08.025.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  48. G. M. Morris, R. Huey, W. Lindstrom, M. F. Sanner, R. K. Belew, D. S. Goodsell, A. J. Olson, J. Comput. Chem., 2009, 30, 2785; DOI: https://doi.org/10.1002/jcc.21256.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Urals Branch, Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi/Akademicheskaya, 620108, Yekaterinburg, Russian Federation

    N. A. Elkina, E. V. Shchegolkov, Ya. V. Burgart & V. I. Saloutin

  2. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Yekaterinburg, Russian Federation

    E. V. Shchegolkov, Ya. V. Burgart & V. I. Saloutin

  3. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny proezd, 142432, Chernogolovka, Moscow Region, Russian Federation

    N. P. Boltneva, O. G. Serebryakova, S. V. Lushchekina & G. F. Makhaeva

  4. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119334, Moscow, Russian Federation

    S. V. Lushchekina

Authors
  1. N. A. Elkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. V. Shchegolkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ya. V. Burgart
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. I. Saloutin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. P. Boltneva
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. O. G. Serebryakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. S. V. Lushchekina
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. G. F. Makhaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. I. Saloutin.

Additional information

The equipment of the Center for Collective Use “Spectroscopy and Analysis of Organic Compounds” was used. The work on molecular modeling was performed using the equipment of the Lomonosov Moscow State University Supercomputer Center.

This work was financially supported by the Russian Foundation for Basic Research (Project No. 20-03-00312).

This work does not involve human participants and animal subjects.

The authors declare no competing of interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 567–572, March, 2021.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Elkina, N.A., Shchegolkov, E.V., Burgart, Y.V. et al. Synthesis of new efficient and selective carboxylesterase inhibitors based on adamantyl and citronellyl 4,4,4-trifluoro-2-arylhydrazonylidene-3-oxobutanoates. Russ Chem Bull 70, 567–572 (2021). https://doi.org/10.1007/s11172-021-3126-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-021-3126-2

Key words

Search

Navigation