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Crystal Structure of 5ʹ-Oxospiro-(fluorene-9,4ʹ-imidazolidine)-2ʹ-thione and Biological Activity of Its Derivatives

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Abstract

The presented study is devoted to the structural and biological properties of four derivatives of fluorenylspirohydantoin based on experimental data. The crystal structure of one of those, (9ʹ-fluorene)-spiro-5-(2-thiohydantoin), is described. The compound crystallizes in monoclinic crystal system and P21/c space group. We have pursued isolation of single crystals and biological activity tests of (9ʹ-fluorene)-spiro-5-hydantoin, (9ʹ-fluorene)-spiro-5-(2,4-dithiohydantoin), (9ʹ-fluorene)-spiro-5-(2-thiohydantoin), and (4ʹ,5ʹ-diaza-9ʹ-fluorene)-spiro-5-hydantoin. The compounds have been tested in both adherent and suspension tumor cell lines. The cell proliferation has been assessed by the WST-assay (Roche Applied Science). The antimicrobial activity against both Gram-positive, Gram-negative bacteria, and the yeast Candida albicans has been studied.

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REFERENCES

  1. Bovy, P.R., Gillet, C., Lenaers, A., Niebes, P., Roba, J., and Lambelin, G., US Patent, 4 853 401, 1989.

  2. Sarges, R., Schnur, R.C., Belletire, J.L., and Peterson, M.J., J. Med. Chem., 1988, vol. 31(1), p. 230. https://doi.org/10.1021/jm00396a037

    Article  CAS  PubMed  Google Scholar 

  3. Suzen, S. and Buyukbingol, E., Il Farmaco, 2000, vol. 55(4), p. 246. https://doi.org/10.1016/S0014-827X(00)00028-8

    Article  CAS  PubMed  Google Scholar 

  4. Rodgers, T.R., LaMontagne, M.P., Markovac, A., and Ash, A.B., J. Med. Chem., 1977, vol. 20(4), p. 591. https://doi.org/10.1021/jm00214a031

    Article  CAS  PubMed  Google Scholar 

  5. Hoffmann, R.W., Sander, T., and Brumm, M., Chem. Ber., 1992, vol. 125(10), p. 2319. https://doi.org/10.1002/cber.19921251020

  6. Oldfield, W. and Cashin, C.H., J. Med. Chem., 1965, vol. 8, p. 239. https://doi.org/10.1021/jm00326a021

    Article  CAS  PubMed  Google Scholar 

  7. Kiec-Kononowicz, K., Stadnicka, K., Mitka, A., Pekala, E., Filipek, B., Sapa, J., and Zygmunt, M., Eur. J. Med. Chem., 2003, vol. 38(6), p. 555. https://doi.org/10.1016/S0223-5234(03)00075-8

    Article  CAS  PubMed  Google Scholar 

  8. Somsak, L., Kovacs, L., Toth, M., Osz, E., Szilagyi, L., Gyorgydeak, Z., Dinya, Z., Docsa, T., Toth, B., and Gergely, P., J. Med. Chem., 2001, vol. 44(17), p. 2843. https://doi.org/10.1021/jm010892t

    Article  CAS  PubMed  Google Scholar 

  9. Marintchev, A., Mirtcheva, J., Sidjimov, A., and Haimova, M., Int. J. Immunopharmacol., 1995, vol. 17(12), p. 981. https://doi.org/10.1016/0192-0561(95)00093-3

    Article  CAS  PubMed  Google Scholar 

  10. Szymaevska, E., Kied-Kononowicz, K., Biaevecka, A., and Kasprowicz, A., Il Farmaco, 2002, vol. 57(1), p. 39. https://doi.org/10.1016/S0014-827X(01)01172-7

    Article  Google Scholar 

  11. Naydenova, E., Pencheva, M., Popova, J., Stoyanov, N., Lazarova, M., and Aleksiev, B., Il Farmaco, 2002, vol. 57(3), p.189. https://doi.org/10.1016/S0014-827X(01)01198-3

    Article  CAS  PubMed  Google Scholar 

  12. Henze, H.R. and Smith, P.E., J. Am. Chem. Soc., 1943, vol. 65(6), p. 1090. https://doi.org/10.1021/ja01246a024

    Article  CAS  Google Scholar 

  13. Carrington, H.C., J. Chem. Soc., 1947, p. 681. https://doi.org/10.1039/JR9470000681

  14. Carrington, H.C., Vasey, C.H., and Waring, W.S., J. Chem. Soc., 1959, p. 396. https://doi.org/10.1039/JR9590000396

  15. Marinov, M., Minchev, S., Stoyanov, N., Ivanova, G., Spassova, M., and Enchev, V., Croat. Chem. Acta, 2005, vol. 78(1), p. 9. https://hrcak.srce.hr/2660

  16. Stoyanov, N., Marinov, M., and Minchev, S., C. R. Acad. Bulg. Sci., 2002, vol. 55(11), p. 61.

    CAS  Google Scholar 

  17. Shivachev, B., Petrova, R., Marinova, P., Stoyanov, N., Ahmedova, A., and Mitewa, M., Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 2006, vol. 62, p. o211. https://doi.org/10.1107/S0108270106003489

  18. Ahmedova, A., Pavlovich, G., Marinov, M., Stoyanov, N., Šišak, D., and Mitewa, M., J. Mol. Struct., 2009, vol. 938, p. 165. https://doi.org/10.1016/j.molstruc.2009.09.021

    Article  CAS  Google Scholar 

  19. Gauthier, T., Yokum, T., Morales, G., McLaughlin, M., Liu, Y.-H., and Fronczek, R., Acta Crystallogr. Sect. C: Cryst. Struct. Commu., 1997, vol. 53, p. 1659. https://doi.org/10.1107/S0108270197007488/fg13322sup3.hkl

    Article  Google Scholar 

  20. Walker, L., Folting, K., and Merritt Junior, L., Acta Crystallogr. Sect. B: Struct. Crystallogr. Cryst. Chem., 1970, vol. 25(26), p. 88. https://doi.org/10.1107/S0567740870001966

    Article  Google Scholar 

  21. Roszak, A. and Weaver, D., Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1998, vol. 54, p. 1168. https://doi.org/10.1107/S0108270197019963

    Article  Google Scholar 

  22. Casas, J., Castineiras, A., Couce, D., Playa, N., Sordo, J., and Varela, J., Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1998, vol. 54, p. 427. https://doi.org/10.1107/S0108270197014960

  23. Todorov, P.T., Nikolova, R.P., Naydenova, E.D., and Shivachev, B.L., J. Chem. Crystallogr., 2012, vol. 42, p. 566. https://doi.org/10.1007/s10870-012-0280-2

  24. Thomas, K.R.J., Lin, J.T., Tsai, C.-M., and Lin, H.-C., Tetrahedron, 2006, vol. 62(15), p. 3517. https://doi.org/10.1016/j.tet.2006.02.001

    Article  CAS  Google Scholar 

  25. Marinov, M., Marinova, P., and Stoyanov, N., Asian Chem. Lett., 2011, vol. 15, nos. 1–2, p. 17.

    Google Scholar 

  26. Ahmedova, A., Marinova, P., Paradowska, K., Marinov, M., and Mitewa, M., J. Mol. Struct., 2008, vol. 892, p. 13. https://doi.org/10.1016/j.molstruc.2008.04.053

    Article  CAS  Google Scholar 

  27. Marinova, P., Marinov, M., Delchev, V., and Stoyanov, N., Acta Chim. Slovenica, 2015, vol. 62, p. 225. https://doi.org/10.17344/acsi.2014.1206

    Article  CAS  Google Scholar 

  28. Marinova, P.E., Marinov, M.N., Kazakova, M.H., Feodorova, Y.N., Sarafian, V.S., and Stoyanov, N.M., Bulg. Chem. Commun., 2015, vol. 47, special issue A, p. 75.

    Google Scholar 

  29. Ahmedova, A., Marinova, P., Marinov, M., and Stoyanov, N., J. Mol. Str., 2016, vol. 1108, p. 602. https://doi.org/10.1016/j.molstruc.2015.12.018

    Article  CAS  Google Scholar 

  30. Marinov, M.N., Marinova, P.E., Markova, N.V., and Stoyanov, N.M., Bulg. Chem. Commun., 2015, vol. 47(4), p. 1022.

    Google Scholar 

  31. Marinova, P., Marinov, M., Kazakova, M., Feodorova, Y., Slavchev, A., Blazheva, D., Georgiev, D., Penchev, P., Sarafian, V., and Stoyanov, N., Acta Chim. Slovenica, 2016, vol. 63, p. 26. https://doi.org/10.17344/acsi.2015.1591

    Article  CAS  Google Scholar 

  32. Marinov, M., Kostova, I., Naydenova, E., Prodanova, R., Marinova, P., Penchev, P., and Stoyanov, N., University of Ruse “Angel Kanchev” Proc., 2015, vol. 54(10.1), p. 17.

    Google Scholar 

  33. Marinov, M., Naydenova, E., Prodanova, R., Markova, N., Marinova, P., Kostova, I., Valcheva, I., Draganova, D., Naydenov, M., and Stoyanov, N., Agric. Sci., 2016, vol. 8(19), p. 117.

    Google Scholar 

  34. Marinova, P., Marinov, M., Kazakova, M., Feodorova, Y., Penchev, P., Sarafian, V., and Stoyanov, N., Biotechnol. Biotec. Eq., 2014, vol. 28(2), p. 316. https://doi.org/10.1080/13102818.2014.910363

    Article  CAS  Google Scholar 

  35. Marinova, P., Marinov, M., Feodorova, Y., Kazakova, M., Georgiev, D., Trendafilova, E., Penchev, P., Sarafian, V., and Stoyanov, N., University of Ruse “Angel Kanchev” Proc., 2013, vol. 52(10.1), p. 33.

    Google Scholar 

  36. Marinova, P., Marinov, M., Feodorova, Y., Kazakova, M., Georgiev, D., Lekova, V., Penchev, P., and Stoyanov, N., C. R. Acad. Bulg. Sci., 2014, vol. 67(4), p. 513.

    CAS  Google Scholar 

  37. Marinova, P., Marinov, M., Feodorova, Y., Kazakova, M., Slavchev, A., Blazheva, D., Sarafian, V., Nikolova, I., and Stoyanov, N., Sci. Technol., 2014, vol. 4(1), p. 112.

    Google Scholar 

  38. Marinov, M., Marinova, P., Penchev, P., and Stoyanov, N., University of Ruse “Angel Kanchev” Proc., 2013, vol. 52(10.1), p. 21.

    Google Scholar 

  39. Sheldrick, G.M., Acta Cryst. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

  40. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Cryst., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

  41. Farrugia, L.J., J. Appl. Cryst., 2012, vol. 45, p. 849. https://doi.org/10.1107/S0021889812029111

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

We are grateful to professor Plamen Penchev, PhD, DSc, of University of Plovdiv for spectra measurements.

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Correspondence to P. Marinova.

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Marinova, P., Marinov, M., Kazakova, M. et al. Crystal Structure of 5ʹ-Oxospiro-(fluorene-9,4ʹ-imidazolidine)-2ʹ-thione and Biological Activity of Its Derivatives. Russ J Gen Chem 91, 939–946 (2021). https://doi.org/10.1134/S1070363221050273

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