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Synthesis of 4,4′-substituted 2,2′-[ethane-1,2-diylbis(selanediyl)]bis(1H-imidazol-5(4H)-ones)

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Russian Chemical Bulletin Aims and scope

Abstract

Synthesis of new bis(seleno-imidazolone) derivatives bearing the alkyl and aryl moieties at the N(1) atom of the five-membered ring was developed. Cytotoxicity of the synthesized compounds against A549, VA-13, MCF-7, and HEK293T cell lines was evaluated.

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References

  1. G. Mugesh, H. Singh, Chem. Soc. Rev., 2000, 29, 347; DOI: https://doi.org/10.1039/A908114C.

    Article  CAS  Google Scholar 

  2. C. Narajji, M. D. Karvekar, A. K. Das, Indian J. Pharm. Sci., 2007, 69, 344; DOI: https://doi.org/10.4103/0250-474X.34541.

    Article  CAS  Google Scholar 

  3. D. Plano, Y. Baquedano, E. Ibánez, I. Jiménez, J. A. Palop, J. E. Spallholz, C. Sanmartín, Molecules, 2010, 15, 7292; DOI: https://doi.org/10.3390/molecules15107292.

    Article  CAS  Google Scholar 

  4. C. F. Bortolatto, P. M. Chagas, E. A. Wilhelm, G. Zeni, C. W. Nogueira, J. Enzyme Inhib., 2013, 28, 677; DOI: https://doi.org/10.3109/14756366.2012.670805.

    Article  CAS  Google Scholar 

  5. S. T. Stefanello, A. S. Prestes, T. Ogunmoyole, S. M. Salman, R. S. Schwab, C. R. Brender, L. Dornelles, J. B. T. Rocha, F. A. A. Soares, Toxicol. in Vitro, 2013, 27, 1433; DOI: https://doi.org/10.1016/j.tiv.2013.03.001.

    Article  CAS  Google Scholar 

  6. A. C. Sauer, J. G. Leal, S. T. Stefanello, M. T. B. Leite, M. B. Souza, F. A. A. Soares, O. E. D. Rodrigues, L. Dornelles, Tetrahedron Lett., 2017, 58, 87; DOI: https://doi.org/10.1016/j.tetlet.2016.11.106.

    Article  CAS  Google Scholar 

  7. K. El-Bayoumy, Cancer Res., 1985, 45, 3631; https://cancerres.aacrjournals.org/content/45/8/3631.short.

    CAS  PubMed  Google Scholar 

  8. P. Sahu, G. Kim, J. Yu, J. Ahn, J. Song, Y. Choi, X. Jin, J. Kim, S. Lee, S. Park, L. Jeong, Org. Lett., 2014, 16, 5796; DOI: https://doi.org/10.1021/ol502899b.

    Article  CAS  Google Scholar 

  9. M. Radhakrishna, C. Sharadamma, M. Vagdevi, M. Abhilekha, S. Rubeena, K. Nischal, Int. J. Chem., 2010, 2, 149; DOI: https://doi.org/10.5539/ijc.v2n2p149.

    CAS  Google Scholar 

  10. G. Roy, G. Mugesh, J. Am. Chem. Soc., 2005, 127, 15207; DOI: https://doi.org/10.1021/ja054497u.

    Article  CAS  Google Scholar 

  11. C. Nogueira, G. Zeni, J. Rocha, Chem. Rev., 2004, 104, 6255; DOI: https://doi.org/10.1021/cr0406559.

    Article  CAS  Google Scholar 

  12. O. Epp, R. Ladenstein, A. Wendel, Eur. J. Biochem., 1983, 133, 51; DOI: https://doi.org/10.1111/j.1432-1033.1983.tb07429.x.

    Article  CAS  Google Scholar 

  13. A. A. Lysova, R. D. Marchenko, D. G. Samsonenko, A. S. Potapov, V. P. Fedina, Russ. Chem. Bull., 2020, 69, 1122; DOI: https://doi.org/10.1007/s11172-020-2877-5.

    Article  CAS  Google Scholar 

  14. Y. Sun, M.-W. Ding, Chin. J. Synth. Chem., 2005, 13, 546, 590.

    CAS  Google Scholar 

  15. A. A. El-Barbary, A. A. Saffan, M. A. Sakran, A. I. Khodair, Delta J. Sci., 1990, 14, 601.

    CAS  Google Scholar 

  16. E. K. Beloglazkina, A. G. Majouga, I. V. Yudin, N. V. Zyk, A. A. Moiseeva, K. P. Butin, Russ. Chem. Bull., 2005, 54, 2163; DOI: https://doi.org/10.1007/s11172-007-0057-5.

    Article  CAS  Google Scholar 

  17. E. K. Beloglazkina, A. G. Majouga, R. B. Romashkina, A. A. Moiseeva, N. V. Zyk, Polyhedron, 2007, 26, 797; DOI: https://doi.org/10.1016/j.poly.2006.09.012.

    Article  CAS  Google Scholar 

  18. A. G. Majouga, E. K. Beloglazkina, O. V. Shilova, A. A. Moiseeva, N. V. Zyk, Russ. Chem. Bull., 2009, 58, 1392; DOI: https://doi.org/10.1007/s11172-009-0185-1.

    Article  CAS  Google Scholar 

  19. E. K. Beloglazkina, A. G. Majouga, A. V. Mironov, A. V. Yudina, O. Yu. Kuznetsova, N. V. Zyk, Polyhedron, 2014, 76, 45; DOI: https://doi.org/10.1016/j.poly.2014.03.045.

    Article  CAS  Google Scholar 

  20. A. Majouga, M. Zvereva, M. Rubtsova, D. Skvortsov, A. Mironov, D. Azhibek, O. Krasnovskaya, V. Gerasimov, A. Udina, N. Vorozhtsov, E. Beloglazkina, L. Agron, L. Mikhina, A. Tretyakova, N. Zyk, N. Zefirov, A. Kabanov, O. Dontsova, J. Med. Chem., 2014, 57, 6252; DOI: https://doi.org/10.1021/jm500154f.

    Article  CAS  Google Scholar 

  21. E. K. Beloglazkina, O. O. Krasnovskaya, D. A. Guk, V. A. Tafeenko, A. A. Moiseeva, N. V. Zyk, A. G. Majouga, Polyhedron, 2018, 148, 129; DOI: https://doi.org/10.1016/j.poly.2018.04.005.

    Article  CAS  Google Scholar 

  22. O. O. Krasnovskaya, D. A. Guk, A. E. Naumov, V. N. Nikitina, A. S. Semkina, K. Yu. Vlasova, V. Pokrovsky, O. O. Ryabaya, S. S. Karshieva, D. A. Skvortsov, I. V. Zhirkina, R. R. Shafikov, P. V. Gorelkin, A. N. Vaneev, A. S. Erofeev, D. M. Mazur, V. A. Tafeenko, V. I. Pergushov, M. Ya. Melnikov, M. A. Soldatov, V. V. Shapovalov, A. V. Soldatov, R. A. Akasov, V. M. Gerasimov, D. A. Sakharov, A. A. Moiseeva, N. V. Zyk, E. K. Beloglazkina, A. G. Majouga, J. Med. Chem., 2020, 63, 13031; DOI: https://doi.org/10.1021/acs.jmedchem.0c01196.

    Article  CAS  Google Scholar 

  23. Y. Sun, L. Gao, M. Ding, Heterocycl. Commun., 2005, 11, 69; DOI: https://doi.org/10.1515/HC.2005.11.1.69.

    CAS  Google Scholar 

  24. M. Yu. Steklov, A. N. Chernysheva, R. L. Antipin, A. G. Majouga, E. K. Beloglazkina, A. A. Moiseeva, E. D. Strel’tsova, N. V. Zyk, Russ. Chem. Bull., 2012, 61, 1182; DOI: https://doi.org/10.1007/slll72-012-0161-z].

    Article  CAS  Google Scholar 

  25. Y. A. Ivanenkov, M. S. Veselov, I. G. Rezekin, D. A. Skvortsov, Y. B. Sandulenk, M. V. Polyakova, D. S. Bezrukov, S. V. Vasilevsky, M. E. Kukushkin, A. A. Moiseeva, A. V. Finko, V. E. Koteliansky, N. L. Klyachko, L. A. Filatova, E. K. Beloglazkina, N. V. Zyk, A. G. Majouga, Bioorg. Med. Chem., 2016, 24, 802; DOI: https://doi.org/10.1016/j.bmc.2015.12.050.

    Article  CAS  Google Scholar 

  26. V. K. Novotortsev, M. E. Kukushkin, V. A. Tafeenko, N. V. Zyk, E. K. Beloglazkina, Mendeleev Commun., 2020, 30, 320; DOI: https://doi.org/10.1016/j.mencom.2020.05.020.

    Article  CAS  Google Scholar 

  27. O. Vyhivskyi, E. A. Dlin, A. V. Finko, S. P. Stepanova, Y. A. Ivanenkov, D. A. Skvortsov, A. V. Mironov, N. V. Zyk, A. G. Majouga, E. K. Beloglazkina, ACS Comb. Sci., 2019, 21, 456; DOI: https://doi.org/10.1021/acscombsci.9b00021.

    Article  CAS  Google Scholar 

  28. O. Vyhivskyi, D. N. Laikov, A. V. Finko, D. A. Skvortsov, I. V. Zhirkina, V. A. Tafeenko, N. V. Zyk, A. G. Majouga, E. K. Beloglazkina, J. Org. Chem., 2020, 85, 3160; DOI: https://doi.org/10.1021/acs.joc.9b03045.

    Article  CAS  Google Scholar 

  29. L. A. Wessjohann, A. Schneider, M. Abbas, W. Brandt, Biol. Chem., 2007, 388, 997; DOI: https://doi.org/10.1515/BC.2007.138.

    Article  CAS  Google Scholar 

  30. N. Sonoda, A. Ogawa, F. Recupero, in Encyclopedia of Reagents for Organic Synthesis, 2005, 1–7; DOI: https://doi.org/10.1002/047084289X.rb018.pub2.

  31. T. Mosmann, J. Immunol. Methods, 1983, 65, 55; DOI: https://doi.org/10.1016/0022-1759(83)90303-4.

    Article  CAS  Google Scholar 

  32. E. S. Antonarakis, Transl. Androl. Urol., 2013, 2, 119; DOI: https://doi.org/10.3978/j.issn.2223-4683.2012.09.04

    PubMed  PubMed Central  Google Scholar 

  33. S. Payton, Nat. Rev. Urol., 2014, 11, 243; DOI: https://doi.org/10.1038/nrurol.2014.98.

    Article  Google Scholar 

  34. D. M. Moran, C. G. Maki, Mol. Cancer. Ther., 2010, 9, 895; DOI: https://doi.org/10.1158/1535-7163.MCT-09-1220.

    Article  CAS  Google Scholar 

  35. H. Shen, C. G Maki, J. Biol. Chem., 2010, 285, 23105; DOI: https://doi.org/10.1074/jbc.M110.124990.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Lomonosov Moscow State University, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    A. V. Finko, A. I. Sokolov, L. A. Vasilyeva, D. A. Skvortsov, N. V. Zyk, A. G. Majouga & E. K. Beloglazkina

  2. Dmitry Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    A. S. H. Al-Khazraji, E. N. Ofitserov & A. G. Majouga

Authors
  1. A. V. Finko
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  2. A. I. Sokolov
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  3. L. A. Vasilyeva
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  4. D. A. Skvortsov
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  5. A. S. H. Al-Khazraji
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  6. E. N. Ofitserov
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  7. N. V. Zyk
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  8. A. G. Majouga
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  9. E. K. Beloglazkina
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Corresponding author

Correspondence to A. V. Finko.

Additional information

This work was performed within the framework of the State assignment of Lomonosov Moscow State University using the equipment of Center of the collective usage of MSU.

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 457–462, March, 2021.

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Finko, A.V., Sokolov, A.I., Vasilyeva, L.A. et al. Synthesis of 4,4′-substituted 2,2′-[ethane-1,2-diylbis(selanediyl)]bis(1H-imidazol-5(4H)-ones). Russ Chem Bull 70, 457–462 (2021). https://doi.org/10.1007/s11172-021-3108-4

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  • DOI: https://doi.org/10.1007/s11172-021-3108-4

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