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Synthesis and analgesic activity of 1,3,5-trisubstituted pyrazoles containing a diterpenoid moiety

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Abstract

Conjugates of terpenoids with 1,3,5-trisubstituted pyrazoles were synthesized by the cross-coupling of methyl 16-(2-chloro-2-oxoacetyl)labdatrienoate with terminal arylacetylenes via the Castro—Stephens reaction and heterocyclization of arylalkyne-1,2-diones with arylhydr-azines. The structure of one reaction product was established by X-ray diffraction. The conditions for the formation of furanolabdanoid arylalkyne-1,2-diones were found. The newly synthesized pyrazoles exhibit analgesic activity in a model of chemical irritation.

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References

  1. E. E. Shul´ts, M. E. Mironov, Yu. V. Kharitonov, Chem. Nat. Compd., 2014, 50, 2.

    Article  Google Scholar 

  2. T. G. Tolstikova, I. V. Sorokina, T. V. Voevoda, E. E. Shul´ts, G. A. Tolstikov, Dokl. AN, 2001, 376, 271.

    CAS  Google Scholar 

  3. H.-S. Chae, Y.-W. Chin, Immunopharm. & Immunotoxicol., 2012, 34, 250.

    Article  CAS  Google Scholar 

  4. M.-S. Lee, S.-O. Lee, S.-H. Kim, E.-O. Lee, H.-J. Lee, Int. J. Mol. Sci., 2016, 17, 1066.

    Article  Google Scholar 

  5. J. H. Lee, H.-J. Lee, D. Y. Sim, J. H. Jung, K. R. Kim, S.-H. Kim, Phytother. Res., 2018, 32, 1755.

    Article  CAS  Google Scholar 

  6. D. S. Ahn, H. J. Lee, J. Hwang, H. Han, B. Kim, B. Shim, S.-H. Kim, Int. J. Mol. Sci., 2018, 19, 1476.

    Article  Google Scholar 

  7. E. E. Shults, J. Velder, H.-G. Schmalz, S. V. Chernov, T. V. Rubalova, Y. V. Gatilov, G. Henze, G. A. Tolstikov, A. Prokop, Bioorg. Med. Chem. Lett., 2006, 16, 4228.

    Article  CAS  Google Scholar 

  8. M. E. Mironov, Y. V. Kharitonov, E. E. Shul´ts, M. M. Shakirov, I. Yu. Bagryanskaya, G. A. Tolstikov, Chem. Nat. Compd., 2010, 46, 233.

    Article  CAS  Google Scholar 

  9. E. A. Morozova, T. G. Tolstikova, E. E. Shults, S. V. Chernov, Y. V. Kharitonov, M. E. Mironov, G. A. Tolstikov, Chem. Sustainable Develop., 2010, 18, 409.

    Google Scholar 

  10. M. E. Mironov, M. A. Pokrovsky, Y. V. Kharitonov, M. M. Shakirov, A. G. Pokrovsky, E. E. Shults, ChemistrySelect, 2016, 1, 417.

    Article  CAS  Google Scholar 

  11. O. I. Kremenko, Yu. V. Kharitonov, E. E. Shul´ts, Russ. J. Org. Chem., 2017, 53, 35.

    Article  CAS  Google Scholar 

  12. J. V. Faria, P. F. Vegi, A. C. C. Miguita, M. C. dos Santos, N. Boechat, A. M. R. Bernardino, Bioorg. Med. Chem., 2017, 25, 5891.

    Article  CAS  Google Scholar 

  13. H. H. Wasserman, C. A. Blum, Tetrahedron Lett., 1994, 35, 9787.

    Article  CAS  Google Scholar 

  14. E. Merkul, J. Dohe, C. Gers, F. Rominger, T. J. J. Müller, Angew. Chem., Int. Ed., 2011, 50, 2966.

    Article  CAS  Google Scholar 

  15. C. Boersch, E. Merkul, T. J. J. Müller, Angew. Chem., Int. Ed., 2011, 50, 10448.

    Article  CAS  Google Scholar 

  16. C. F. Gers, J. Nordmann, C. Kumru, W. Frank, T. J. J. Müller, J. Org. Chem., 2014, 79, 3296.

    Article  CAS  Google Scholar 

  17. Z. Zhang, X. Jiang, Org. Lett., 2014, 16, 4400.

    Article  CAS  Google Scholar 

  18. A. K. Mukherjee, P. Margaretha, W. C. Agosta, J. Org. Chem., 1996, 61, 3388.

    Article  CAS  Google Scholar 

  19. Y. Liu, M. Liu, S. Guo, H. Tu, Y. Zhou, H. Gao, Org. Lett., 2006, 8, 3445.

    Article  CAS  Google Scholar 

  20. Z. Zhang, Z. Dai, X. Jiang, Asian J. Org. Chem., 2016, 5, 52.

    Article  CAS  Google Scholar 

  21. X. Kong, G. Zhang, S. Yang, X. Liu, X. Fang, Adv. Synth. Catal., 2017, 359, 2729.

    Article  CAS  Google Scholar 

  22. I. A. Ibarra, A. Islas-Jácome, E. González-Zamora, Org. Biomol. Chem., 2018, 16, 1402.

    Article  CAS  Google Scholar 

  23. C. G. Neochoritis, T. Zhao, A. Domling, Chem. Rev., 2019, 119, 1970.

    Article  CAS  Google Scholar 

  24. F. S. Al-Hajjar, S. S. Sabri, J. Heterocycl. Chem., 1986, 23, 727.

    Article  CAS  Google Scholar 

  25. B. S. Holla, K. V. Udupa, K. P. Sridhar, Bull. Chem. Soc. Jpn, 1989, 62, 3409.

    Article  CAS  Google Scholar 

  26. J. P. Waldo, S. Mehta, R. C. Larock, J. Org. Chem., 2008, 73, 6666.

    Article  CAS  Google Scholar 

  27. M. Zora, A. Kivrak, C. Yazici, J. Org. Chem., 2011, 76, 6726.

    Article  CAS  Google Scholar 

  28. V. A. Savel´ev, A. A. Kotova, T. V. Rybalova, E. E. Shults, Chem. Heterocycl. Compd., 2019, 55, 943.

    Article  Google Scholar 

  29. F. H. Allen, O. Kenard, D. G. Watson, L. Bramer, A. G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, 1.

    Google Scholar 

  30. Cambridge Structural Database, Version 5.39, University of Cambridge, UK.

  31. F. H. Allen, Acta Crystallogr., Sect. B, 2002, 58, 380.

    Article  Google Scholar 

  32. R. S. Rowland, R. Taylor, J. Phys. Chem., 1996, 100, 7384.

    Article  CAS  Google Scholar 

  33. G. M. Sheldrick, SADABS, Program for Area Detector Adsorption Correction, Institute for Inorganic Chemistry, University of Goettingen (Germany), 1996.

    Google Scholar 

  34. G. M. Sheldrick, SHELX-97, Programs for Crystal Structure Analysis, Release 97-2, University of Göttingen, Göttingen (Germany).

  35. R. Koster, M. Anderson, E. J. De Beer, Fed. Proc. 1959, 18, 412.

    Google Scholar 

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrentieva, 630090, Novosibirsk, Russian Federation

    M. E. Mironov, A. I. Poltanovich, T. V. Rybalova, M. P. Dolgikh, T. G. Tolstikova & E. E. Shults

  2. Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation

    M. E. Mironov, A. I. Poltanovich & T. G. Tolstikova

Authors
  1. M. E. Mironov
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  2. A. I. Poltanovich
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  3. T. V. Rybalova
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  4. M. P. Dolgikh
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  5. T. G. Tolstikova
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  6. E. E. Shults
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Corresponding author

Correspondence to E. E. Shults.

Additional information

Dedicated to Academician of the Russian Academy of Sciences M. S. Yunusov on the occasion of his 80th birthday.

We would like to acknowledge the staff of the Multi-Access Chemical Service Center of the Siberian Branch of the Russian Academy of Sciences for spectral and analytical measurements.

This study was financially supported by the Russian Science Foundation (Project Nos 17-73-10274 and 18-13-00361).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0537–0546, March, 2020.

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Mironov, M.E., Poltanovich, A.I., Rybalova, T.V. et al. Synthesis and analgesic activity of 1,3,5-trisubstituted pyrazoles containing a diterpenoid moiety. Russ Chem Bull 69, 537–546 (2020). https://doi.org/10.1007/s11172-020-2795-6

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  • DOI: https://doi.org/10.1007/s11172-020-2795-6

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