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Molecular design of N,N-disubstituted 2-aminothiazolines as selective carboxylesterase inhibitors

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Abstract

Selective carboxylesterase inhibitors are employed as modulators of hydrolytic metabolism of ester or amide-containing drugs. Using the Molecular Field Topology Analysis (MFTA), the models for the relationships between the structures and inhibitory activities of 5-halomethyl-2-aminothiazolines against acetylcholinesterase, butyrylcholinesterase, and carboxylesterase were built, the molecular design was performed, and a focused library of potentially active and selective carboxylesterase inhibitors was proposed.

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References

  1. P. M. Potter, R. M. Wadkins, Curr. Med. Chem., 2006, 13, 1045.

    Article  CAS  Google Scholar 

  2. S. C. Laizure, V. Herring, Z. Hu, K. Witbrodt, R. B. Parker, Pharmacotherapy, 2013, 33, 210.

    Article  CAS  Google Scholar 

  3. T. Imai, J. Pestic. Sci., 2010, 35, 229.

    Article  CAS  Google Scholar 

  4. M. J. Hatfield, P. M. Potter, Expert Opin. Ther. Pat., 2011, 21, 1159.

    Article  CAS  Google Scholar 

  5. G. M. Simon, B. F. Cravatt, J. Biol. Chem., 2010, 285, 11051.

    Article  CAS  Google Scholar 

  6. G. F. Makhaeva, E. V. Radchenko, I. I. Baskin, V. A. Palyulin, R. J. Richardson, N. S. Zefirov, SAR QSAR Env. Res., 2012, 23, 627.

    Article  CAS  Google Scholar 

  7. L. G. Tsurkan, M. J. Hatfield, C. C. Edwards, J. L. Hyatt, P. M. Potter, Chem. Biol. Interact., 2013, 203, 226.

    Article  CAS  Google Scholar 

  8. G. F. Makhaeva, E. V. Radchenko, V. A. Palyulin, E. V. Rudakova, A. Yu. Aksinenko, V. B. Sokolov, N. S. Zefirov, R. J. Richardson, Chem. Biol. Interact., 2013, 203, 231.

    Article  CAS  Google Scholar 

  9. E. Heymann, K. Krisch, Hoppe-Seyler´s Z. Physiol. Chem., 1967, 348, 609.

    Article  CAS  Google Scholar 

  10. E. V. Rudakova, G. F. Makhaeva, T. G. Galenko, A. Y. Aksinenko, V. B. Sokolov, I. V. Martynov, Dokl. Biochem. Biophys. (Engl. Transl.), 2013, 449, 87 [Dokl. Akad. Nauk, 2013, 449, 232].

    Article  CAS  Google Scholar 

  11. G. R. Mukhamadieva, N. P. Boltneva, T. G. Galenko, V. B. Sokolov, T. A. Epishina, G. F. Makhaeva, Pharm. Chem. J. (Engl. Transl.), 2012, 46, 461 [Khim.-Farm. Zh., 2012, 46, No. 8, 3].

    Article  CAS  Google Scholar 

  12. 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. (Engl. Transl.), 2015, 465, 381 [Dokl. Akad. Nauk, 2015, 465, 367].

    Article  CAS  Google Scholar 

  13. N. P. Boltneva, O. G. Serebryakova, G. F. Makhaeva, I. V. Serkov, A. N. Proshin, S. O. Bachurin, Dokl. Biochem. Biophys. (Engl. Transl.), 2013, 451, 209 [Dokl. Akad. Nauk, 2013, 451, 574].

    Article  CAS  Google Scholar 

  14. S. Lushchekina, G. Makhaeva, N. Boltneva, O. Serebryakova, A. Proshin, I. Serkov, S. Bachurin, 20th EuroQSAR Understanding Chemical-Biological Interactions, Saint-Petersburg, Russia, August 31—September 4, 2014, 158

    Google Scholar 

  15. G. F. Makhaeva, N. P. Boltneva, S. V. Lushchekina, O. G. Serebryakova, T. S. Stupina, A. A. Terentiev, I. V. Serkov, A. N. Proshin, S. O. Bachurin, R. J. Richardson, Bioorg. Med. Chem., 2016, 24, 1050.

    Article  CAS  Google Scholar 

  16. G. L. Ellman, K. D. Courtney, V. Andres, Jr., R. M. Feather-Stone, Biochem. Pharmacol., 1961, 7, 88.

    Article  CAS  Google Scholar 

  17. S. H. Sterri, B. A. Johnesen, F. Fonnun, Biochem. Pharmacol., 1985, 34, 2779.

    Article  CAS  Google Scholar 

  18. V. A. Palyulin, E. V. Radchenko, N. S. Zefirov, J. Chem. Inf. Comp. Sci., 2000, 40, 659.

    Article  CAS  Google Scholar 

  19. E. V. Radchenko, V. A. Palyulin, N. S. Zefirov, in Chemoinformatics Approaches to Virtual Screening, Ed. A. Varnek, A. Tropsha, RSC, Cambridge, 2008, p. 150.

  20. E. V. Radchenko, G. F. Makhaeva, V. V. Malygin, V. B. Sokolov, V. A. Palyulin, N. S. Zefirov, Dokl. Biochem. Biophys. (Engl. Transl.), 2008, 418, 47 [Dokl. Akad. Nauk, 2008, 418, 837].

    Article  CAS  Google Scholar 

  21. E. V. Radchenko, G. F. Makhaeva, V. B. Sokolov, V. A. Palyulin, N. S. Zefirov, Dokl. Biochem. Biophys. (Engl. Transl.), 2009, 429, 309 [Dokl. Akad. Nauk, 2009, 429, 406].

    Article  CAS  Google Scholar 

  22. E. V. Radchenko, A. A. Mel´nikov, G. F. Makhaeva, V. A. Palyulin, N. S. Zefirov, Dokl. Biochem. Biophys. (Engl. Transl.), 2012, 443, 91 [Dokl. Akad. Nauk, 2012, 443, 382].

    Article  CAS  Google Scholar 

  23. A. A. Mel’nikov, V. A. Palyulin, E. V. Radchenko, N. S. Zefirov, Dokl. Chem. (Engl. Transl.), 2007, 415, 196 [Dokl. Akad. Nauk, 2007, 415, 763].

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, 1/3 Leninskie Gory, 119991, Moscow, Russian Federation

    E. V. Radchenko, V. A. Palyulin & N. S. Zefirov

  2. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi pr., 142432, Chernogolovka, Moscow Region, Russian Federation

    E. V. Radchenko, G. F. Makhaeva, N. P. Boltneva, O. G. Serebryakova, I. V. Serkov, A. N. Proshin, V. A. Palyulin & N. S. Zefirov

Authors
  1. E. V. Radchenko
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  2. G. F. Makhaeva
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  3. N. P. Boltneva
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  4. O. G. Serebryakova
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  5. I. V. Serkov
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  6. A. N. Proshin
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  7. V. A. Palyulin
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  8. N. S. Zefirov
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Corresponding author

Correspondence to E. V. Radchenko.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0570—0575, February, 2016.

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Radchenko, E.V., Makhaeva, G.F., Boltneva, N.P. et al. Molecular design of N,N-disubstituted 2-aminothiazolines as selective carboxylesterase inhibitors. Russ Chem Bull 65, 570–575 (2016). https://doi.org/10.1007/s11172-016-1339-6

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  • DOI: https://doi.org/10.1007/s11172-016-1339-6

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