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Synthesis of tetracyclic thienotriazolopyridines based on hydrazine derivatives of fused pyridinethiones

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Abstract

A method for the synthesis of hydrazine derivatives of fused pyridinethiones based on alicyclic and heterocyclic ketones has been developed. Successive heterocyclization of these hydrazine derivatives was carried out in order to obtain new derivatives of tricyclic triazolo[4,3-a]pyridines, tetracyclic thieno[3,2-e][1,2,4]triazolo[4,3-a]pyridines, as well as a new heterocyclic system of thieno[2,3-c][1,2,4]triazolo[3,4-a]-2,7-naphthyridine.

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References

  1. T. Eicher, S. Hauptmann, The Chemistry of Heterocycles. Structure, Reactions, Synthesis and Applications, 2-nd edn., Wiley-VCH, Weinheim, 2003.

    Book  Google Scholar 

  2. A. A. Altaf, A. Shahzad, Z. Gul, N. Rasool, A. Badshah, B. Lal, E. Khan, J. Drug Design Med. Chem., 2015, 1(1), 1; DOI: https://doi.org/10.11648/j.jddmc.20150101.11.

    Google Scholar 

  3. S. R. Alizadeh, M. A. Ebrahimzadeh, Mini Rev. Med. Chem., 2021, 21(17), 2584; DOI: https://doi.org/10.2174/1389557521666210126143558.

    Article  CAS  Google Scholar 

  4. V. V. Dotsenko, D. S. Buryi, D. Y. Lukina, S. G. Krivokolyskov, Russ. Chem. Bull., 2020, 69, 1829; DOI: https://doi.org/10.1007/s11172-020-2969-2.

    Article  CAS  Google Scholar 

  5. M. Lavanya, C. Lin, J. Mao, D. Thirumalai, S. R. Aabaka, X. Yang, J. Mao, Z. Huang, J. Zhao, Top. Curr. Chem. (Cham), 2021, 379, 13; DOI: https://doi.org/10.1007/s41061-020-00314-6.

    Article  CAS  Google Scholar 

  6. V. A. Glushkov, D. N. Babentzev, M. V. Dmitriev, I. A. Borisova, M. S. Denisov, Russ. Chem. Bull., 2021, 70, 122; DOI: https://doi.org/10.1007/s11172-021-3065-y.

    Article  CAS  Google Scholar 

  7. E. G. Paronikyan, Sh. Sh. Dashyan, A. S. Noravyan, R. A. Tamazyan, A. G. Ayvazya, H. A. Panosyan, Tetrahedron, 2015, 71, 2686; DOI: https://doi.org/10.1016/j.tet.2015.03.040.

    Article  CAS  Google Scholar 

  8. E. G. Paronikyan, Sh. Sh. Dashyan, S. S. Mamyan, A. G. Ayvazyan, J. Het. Chem., 2021, 58, 1936; DOI: https://doi.org/10.1002/jhet.4319.

    Article  CAS  Google Scholar 

  9. R. M. Zaki, A. M. Kamal El-Dean, Sh. M. Radwan, A. S. Sayed, ACS Omega, 2020, 5, 252; DOI: https://doi.org/10.1021/acs.omega9b02604.

    Article  CAS  Google Scholar 

  10. N. Bhardwaj, A. Pathania, P. Kumar, Curr. Trad. Med., 2021, 7, 5; DOI: https://doi.org/10.2174/2215083805666190613125700.

    Article  CAS  Google Scholar 

  11. S. Ayvaz, M. Çankaya, A. Atasever, A. Altuntas, J. Enzime Inhib. Med. Chem., 2013, 28, 305; DOI: https://doi.org/10.3109/14756366.2011.639016.

    Article  Google Scholar 

  12. S. T. Nquyan, S. M. Kwasny, X. Ding, S. C. Cardinale, C. T. Mccarthy, H. S. Kim, H. Nikaido, N. P. Peet, J. D. Williams, T. L. Bowlen, T. L. Opperman, Bioorg. Med. Chem., 2015, 23, 2024; DOI: https://doi.org/10.1016/j.bmc.2015.03.016.

    Article  Google Scholar 

  13. Z. Aron, T. J. Opperman, Curr. Opin Microbiol., 2016, 33, 1; DOI: https://doi.org/10.1016/j.mib.2016.05.007.

    Article  CAS  Google Scholar 

  14. T. J. Opperman, S. M. Kwasny, H.-S. Kim, S. T. Nguyen, Ch. Houseweart, S. D’Souza, G. C. Walker, N. P. Peet, H. Nikaido, T. L. Bowlina, Antimicrobial Agents and Chemotherapy, 2014, 58, 722; DOI: https://doi.org/10.1128/aac.01866-13.

    Article  Google Scholar 

  15. E. V. Babaev, Ya. I. Koval, V. B. Rybakov, E. G. Paronikyan, G. M. Stepanyan, R. G. Paronikyan, Sh. Sh. Dashyan, S. A. Rzhevsky, N. A. Shadrin, Russ. Chem. Bull., 2018, 67, 313; DOI: https://doi.org/10.1007/s11172-018-2076-9.

    Article  CAS  Google Scholar 

  16. A. Wójcicka, Curr. Org. Chem., 2021, 25(22), 2740; DOI: https://doi.org/10.2174/1385272825666210812102815.

    Article  Google Scholar 

  17. N. Kandepedu, D. G. Cabrera, S. Eudubilli, D. Taylor, Ch. Brunchwig, L. Gibhard, M. Njoroge, N. Lawrence, T. Paquet, Ch. J. Eyermann, T. Spangenberg, G. S. Basarab, L. J. Street, K. Chibale, J. Med. Chem., 2018, 61, 5692; DOI: https://doi.org/10.1021/acs.jmedchem.8b00648.

    Article  CAS  Google Scholar 

  18. N. A. Haverkate, E. Leung, L. I. Pilkington, D. Barker, Pharmaceutics, 2021, 13, 2020; DOI: https://doi.org/10.3390/pharmaceutics13122020.

    Article  CAS  Google Scholar 

  19. H. J. Arabshahi, M. van Rensburg, L. I. Pilkington, Ch. Y. Jeon, M. Song, L.-M. Gridel, E. Leung, D. Barker, M. V.-Ross, K. P. Volcho, A. L. Zakharenko, O. I. Lavrik, J. Reynisson, Med. Chem. Comm., 2015, 6, 1987; DOI: https://doi.org/10.1039/C5MD00245A.

    Article  CAS  Google Scholar 

  20. M. A. Elsherif, J. Appl. Pharm. Sci., 2021, 11(6), 118; DOI: https://doi.org/10.7324/JAPS.2021.110614.

    CAS  Google Scholar 

  21. A. M. G. Gonçalo, M. A. Vieira-Coelho, Eur. J. Clinic. Pharmacol., 2021, 77, 1623; DOI: https://doi.org/10.1007/s00228-021-03161-6.

    Article  Google Scholar 

  22. R. A. Azzam, G. H. Elgemeie, Med. Chem. Res., 2019, 28, 62; DOI: https://doi.org/10.1007/s00044-018-2264-z.

    Article  CAS  Google Scholar 

  23. C. J. A. Ribeiro, J. Kankanala, J. Xie, J. Williams, H. Aihara, Z. Wang, Bioorg. Med. Chem. Lett., 2019, 29(2), 257; DOI: https://doi.org/10.1016/j.bmcl.2018.11.044.

    Article  CAS  Google Scholar 

  24. R. Nakajima, H. Oono, S. Sugiyama, Y. Matsueda, T. Ida, Sh. Kakuda, J. Hirata, A. Baba, A. Makino, R. Matsuyama, R. D. White, R. P. Wurz, Y. Shin, X. Min, A. Guzman-Perez, Z. Wang, A. Symons, S. K. Singh, S. R. Mothe, S. Belyakov, A. Chakrabarti, S. Shuto, CS Med. Chem. Lett., 2020, 11, 528; DOI: https://doi.org/10.1021/acsmedchemlett.9b00649.

    Article  CAS  Google Scholar 

  25. H. Ryu, K.-Y. Nam, H. J. Kim, J.-Y. Song, S.-G. Hwang, J. S. Kim, J. Kim, J. Ahn, Int. J. Mol. Sci., 2021, 22, 7330; DOI: https://doi.org/10.3390/ijms22147330.

    Article  CAS  Google Scholar 

  26. R. I. Ishmetova, I. N. Ganebnykh, N. K. Ignatenko, S. G. Tolshchina, A. V. Korotina, O. S. Eltsov, M. A. Kravchenko, G. L. Rusinov, Russ. Chem. Bull., 2021, 70, 1093; DOI: https://doi.org/10.1007/s11172-021-3189-0.

    Article  CAS  Google Scholar 

  27. E. G. Paronikyan, A. Petrou, M. Fesatidou, A. Geronikaki, Sh. Sh. Dashyan, S. S. Mamyan, R. G. Paronikyan, I. M. Nazaryan, H. H. Hakopyan, Med. Chem. Comm., 2019, 10, 1399; DOI: https://doi.org/10.1039/c9md00187e.

    Article  CAS  Google Scholar 

  28. A. M. Kamal, S. M. Radwan, R. M. Zaki, Eur. J. Med. Chem., 2011, 46, 567; DOI: https://doi.org/10.1016/j.ejmech.2010.11.036.

    Article  CAS  Google Scholar 

  29. E. G. Paronikyan, Sh. Sh. Dashyan, S. S. Mamyan, Mendeleev Commun., 2020, 30, 183; DOI: https://doi.org/10.1016/j.mencom.2020.03.017.

    Article  CAS  Google Scholar 

  30. E. G. Paronikyan, A. S. Noravyan, Chem. Heterocycl. Compd., 1999, 35, 799; DOI: https://doi.org/10.1007/BF02252103.

    Article  CAS  Google Scholar 

  31. K. Gewald, J. Prakt. Chem., 1966, 32, 205; DOI: https://doi.org/10.1002/prac.19660310312.

    Article  Google Scholar 

  32. E. G. Paronikyan, Sh. F. Akopyan, A. S. Noravyan, Khim. Zhurn. Armenii [Armenian Chem. J.], 2009, 62(1–2), 140; https://arar.sci.am/dlibra/publication/203293 (in Russian).

    CAS  Google Scholar 

  33. E. G. Paronikyan, G. V. Mirzoyan, A. S. Noravyan, D. A. Avakimyan, Yu. Z. Ter-Zakharyan, Pharm. Chem. J., 1993, 27, 759; DOI: https://doi.org/10.1007/BF00780403.

    Article  Google Scholar 

  34. K. Gewald, M. Buchwalder, M. Peukert, J. Prakt. Chem., 1973, 315, 679; DOI: https://doi.org/10.1002/prac.19733150413.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 prosp. Azatutyan, 0014, Yerevan, Republic of Armenia

    E. G. Paronikyan, Sh. Sh. Dashyan, A. S. Harutyunyan, S. S. Mamyan & E. S. Safaryan

Authors
  1. E. G. Paronikyan
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  2. Sh. Sh. Dashyan
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  3. A. S. Harutyunyan
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  4. S. S. Mamyan
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  5. E. S. Safaryan
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Corresponding author

Correspondence to E. G. Paronikyan.

Additional information

Based on the materials of the All-Russian Congress on the Chemistry of Heterocyclic Compounds (October 12–16, 2021, Sochi, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1019–1026, May, 2022.

This work was financially supported by the Science Commitee of the Republic of Armenia (Project No. 21T-1D231).

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Paronikyan, E.G., Dashyan, S.S., Harutyunyan, A.S. et al. Synthesis of tetracyclic thienotriazolopyridines based on hydrazine derivatives of fused pyridinethiones. Russ Chem Bull 71, 1019–1026 (2022). https://doi.org/10.1007/s11172-022-3503-5

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  • DOI: https://doi.org/10.1007/s11172-022-3503-5

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