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Synthesis of 4H-pyrrolo[3,2,1-ij]quinoline-1,2-diones containing a piperazine fragment and study of their inhibitory properties against protein kinases

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Abstract

Hybrid compounds based on 4,4,6-trimethyl-4H-pyrrolo[3,2,1-ij]quinoline-1,2-diones containing a piperazine fragment were synthesized. Their inhibitory activity against protein kinases NPM1-ALK, ALK, EGFR[L858R][T790], EGFR[L858R], JAK2, and JAK3 was investigated. Compounds with inhibitory activity against protein kinase JAK3 at a level of 16.7 µmol L−1 were obtained.

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References

  1. C. Viegas-Junior, A. Danuello, V. da Silva Bolzani, E. J. Barreiro, C. A. Manssour Fraga, Curr. Med. Chem., 2007, 14, 1829; DOI: https://doi.org/10.2174/092986707781058805.

    Article  CAS  Google Scholar 

  2. C. Lazar, A. Kluczyk, T. Kiyota, Y. Konishi, J. Med. Chem., 2004, 47, 6973; DOI: https://doi.org/10.1021/jm049637.

    Article  CAS  Google Scholar 

  3. B. Meunier, Acc. Chem. Res., 2008, 41, 69; DOI: https://doi.org/10.1021/ar7000843.

    Article  CAS  Google Scholar 

  4. L. F. Tietze, H. P. Bell, S. Chandrasekh, Angew. Chem. Int. Ed. Engl., 2003, 42, 3996; DOI: https://doi.org/10.1002/anie.200200553.

    Article  CAS  Google Scholar 

  5. G. Mehta, V. Singh, Chem. Soc. Rev., 2002, 31, 324; DOI: https://doi.org/10.1039/b204748a.

    Article  CAS  Google Scholar 

  6. L. M. Lima, E. J. Barreiro, Curr. Med. Chem., 2005, 12, 23; DOI: https://doi.org/10.2174/0929867053363540.

    Article  CAS  Google Scholar 

  7. M. E. Welsch, S. A. Snyder, B. R. Stockwell, Curr. Opin. Chem. Biol., 2010, 14, 347; DOI: https://doi.org/10.1016/j.cbpa.2010.02.018.

    Article  CAS  Google Scholar 

  8. R. W. DeSimone, K. S. Currie, S. A. Mitchell, J. W. Darrow, D. A. Pippin, Comb. Chem. High Throughput Screen., 2004, 7, 473; DOI: https://doi.org/10.2174/1386207043328544.

    Article  CAS  Google Scholar 

  9. M. D. Mashkovsky, Lekarstvennyye sredstva [Medicines], Novaya volna, Moscow, 2012, 1216 pp. (in Russian).

    Google Scholar 

  10. H. R. Munson, US Pat. 4198414, 1980.

  11. E. V. Leshcheva, S. M. Medvedeva, Kh. S. Shikhaliev, Zh. Org. Farm. Khim., 2014, 12 (No. 2), 15.

    CAS  Google Scholar 

  12. L. Matesic, J. M. Locke, K. Vine, M. Ranson, J. B. Bremner, D. Skropeta, Tetrahedron, 2012, 68, 6810; DOI: https://doi.org/10.1016/j.tet.2012.06.049.

    Article  CAS  Google Scholar 

  13. S. M. Medvedeva, A. Yu. Potapov, I. V. Gribkova, E. V. Katkova, V. B. Sulimov, Kh. S. Shikhaliev, Pharm. Chem. J., 2018, 51, 975; DOI: https://doi.org/10.1007/s11094-018-1726-4.

    Article  CAS  Google Scholar 

  14. R. Kharb, K. Bansal, A. K. Sharma, Der Pharma Chemica, 2012, 4, 2470.

    CAS  Google Scholar 

  15. S. D. Desai, A. G. Mehta, Res. J. Chem. Sci., 2014, 4, No. 5, 14.

    Google Scholar 

  16. P. Chaudhary, R. Kumar, A. K. Verma, D. Singh, V. Yadav, A. K. Chhillar, G. L. Sharmab, R. Chandra, Bioorg. Med. Chem., 2006, 14, 1819; DOI: https://doi.org/10.1016/j.bmc.2005.10.032.

    Article  CAS  Google Scholar 

  17. K. K. Singh, S. C. Joshi, C. S. Mathela, Ind. J. Chem., 2011, 50B, 196.

    CAS  Google Scholar 

  18. A. Mermer, S. Demirci, S. B. Ozdemir, A. Demirbas, S. Ulker, F. A. Ayaz, F. Aksakal, N. Demirbas, Chin. Chem. Lett., 2017, 28, 995; DOI: https://doi.org/10.1016/j.cclet.2016.12.012.

    Article  CAS  Google Scholar 

  19. M. Mentese, N. Demirbas, A. Mermer, S. Demirci, A. Demirbas, F. A. Ayaz, Lett. Drug Design Disc., 2018, 15, 46; DOI: https://doi.org/10.2174/1570180814666170113145023.

    Article  CAS  Google Scholar 

  20. S. B. Ozdemir, N. Demirbas, Y. U. Cebeci, H. Bayrak, A. Mermer, S. Ceylan, A. Demirbas, Lett. Drug Design Disc., 2017, 14, 1014; DOI: https://doi.org/10.2174/1570180814666170113145023.

    Article  CAS  Google Scholar 

  21. J. A. Wiles, B. J. Bradbury, M. J. Pucci, Expert Opin. Ther. Pat., 2010, 20, 1295; DOI: https://doi.org/10.1517/13543776.2010.505922.

    Article  CAS  Google Scholar 

  22. G. I. Zhungietu, M. A. Rekhter, Izatin i ego proizvodnye [Izatin and Its Derivatives], Shtiintsa, Chisinau, 1977, 228 pp. (in Russian).

    Google Scholar 

  23. E. V. Leshcheva, Kh. S. Shikhaliev, G. V. Shatalov, G. I. Ermolova, Izv. Vuzov Khim. Khim. Tekhnol. [Univ. Bull. Khim. Khim. Tekhnol.], 2003, 46, No. 5, 105 (in Russian).

    CAS  Google Scholar 

  24. S. M. Medvedeva, Kh. S. Shikhaliev, E. V. Leshcheva, A. S. Solov’ev, Vestnik VSU. Ser. Khim. Biol. Farm. [Voronezh Univ. Lett. Ser. Chem. Biol. Pharm.], 2005, No. 2, 54 (in Russian).

    Google Scholar 

  25. S. M. Medvedeva, Kh. S. Shikhaliev, G. S. Sanina, A. S. Solov’ev, Butlerov. Soobshch. [Butlerov Commun.], 2006, 8, 37 (in Russian).

    Google Scholar 

  26. S. M. Medvedeva, A. L. Sabynin, Kh. S. Shikhaliev, Russ. Chem. Bull., 2014, 63, 2693; DOI: https://doi.org/10.1007/s11172-014-0801-6.

    Article  CAS  Google Scholar 

  27. J. P. Brown, L. M. Jackman, J. Chem. Soc., 1964, 3132; DOI: https://doi.org/10.1039/JR9640003132.

  28. I. Saikia, A. J. Borah, P. Phukan, Chem. Rev., 2016, 116, 6837; DOI: https://doi.org/10.1021/acs.chemrev.5b00400.

    Article  CAS  Google Scholar 

  29. J. P. Brown, O. Meth-Cohn, J. Chem. Soc. (C), 1971, 3631; DOI: https://doi.org/10.1039/J39710003631.

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Correspondence to Kh. S. Shikhaliev.

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This work was financially supported by the Russian Science Foundation (Project No. 18-74-10097).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0787–0792, April, 2020.

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Novichikhina, N.P., Shestakov, A.S., Potapov, A.Y. et al. Synthesis of 4H-pyrrolo[3,2,1-ij]quinoline-1,2-diones containing a piperazine fragment and study of their inhibitory properties against protein kinases. Russ Chem Bull 69, 787–792 (2020). https://doi.org/10.1007/s11172-020-2834-3

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  • DOI: https://doi.org/10.1007/s11172-020-2834-3

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