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Synthesis of 6b,11b-dihydroxy-12-methylphenyl-11b,12-dihydrobenzo- [g]indeno[1,2-b]indole-5,6,7(6bH)-triones and 2-(3-hydroxy- 4,9-dioxo-4,9-dihydro-1H-benzo[f]indol-2-yl)benzamides, their structure and antiproliferative activity

Methods of synthesis of 6b,11b-dihydroxy-12-methylphenyl-11b,12-dihydrobenzo[g]indeno[1,2-b]indole-5,6,7(6bH)-triones and 2-(3-hydroxy-4,9-dioxo-4,9-dihydro-1H-benzo[f]indol-2-yl)benzamides are proposed. It was found that 6b,11b-dihydroxy-12-(3-methylphenyl)- 11b,12-dihydrobenzo[g]indeno[1,2-b]indole-5,6,7(6bH)-trione exists as two stereoisomers. The antiproliferative activity of 6b,11b-dihydroxy-12-methylphenyl-11b,12-dihydrobenzo[g]indeno[1,2-b]indole-5,6,7(6bH)-triones and 2-(3-hydroxy-4,9-dioxo-4,9-dihydro- 1H-benzo[f]indol-2-yl)benzamides against human tumor and nontumor cells along with the features of their structures that are important for the manifestation of this activity has been established.

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References

  1. 1.

    Laatsch, H.; Fotso, S. In Topics in Current Chemistry; Krohn, K., Ed.; Springer: Heidelberg, 2008, Vol. 282, p. 4.

  2. 2.

    O'Brien, P. J. Chem. Biol. Interact.1991, 80, 1.

  3. 3.

    Gornostaev, L. M.; Tsvetkov, V. B.; Markova, A. A.; Lavrikova, T. I.; Khalyavina, Y. G.; Kuznetsova, A. S.; Kaluzhny, D. N.; Shunayev, A. V.; Tsvetkova, M. V.; Glazunova, V. A.; Chernyshev, V. V.; Shtil, A. A. Anti- Cancer Agents Med. Chem.2017, 17, 1814.

  4. 4.

    Shchekotikhin, A. E.; Glazunova, V. A.; Dezhenkova, L. G.; Shevtsova, E. K.; Traven, V. F.; Balzarini, J.; Huang, H.-S.; Shtil, A. A.; Preobrazhenskaya, M. N. Eur. J. Med. Chem.2011, 46, 423.

  5. 5.

    Shchekotikhin, A. E.; Glazunova, V. A.; Dezhenkova, L. G.; Luzikov, Y. N.; Sinkevich, Y. B.; Kovalenko, L. V.; Buyanov, V. N.; Balzarini, J.; Huang, F.-C.; Lin, J.-J.; Huang, H.-S.; Shtil, A. A.; Preobrazhenskaya, M. N. Bioorg. Med. Chem.2009, 17, 1861.

  6. 6.

    Reddy, H. R.; Reddy, C. V. S.; Subashini, R.; Roopan, S. M. RSC Adv.2014, 4, 29999.

  7. 7.

    Lobo, G.; Monasterios, M.; Rodrigues, J.; Gamboa, N.; Capparelli, M. V.; Martínez-Cuevas, J.; Lein, M.; Jung, K.; Abramjuk, K; Charris, J. Eur. J. Med. Chem.2015, 96, 281.

  8. 8.

    Pathak, S.; Das, D.; Kundu, A.; Maity, S.; Guchhait, N.; Pramanik, A. RSC Adv.2015, 5, 17308.

  9. 9.

    El-Kholy, I. El-S.; Mishrikey, M. M.; Feid-Allah, H. M. J. Heterocycl. Chem.1981, 18, 105.

  10. 10.

    Muthuraman, S.; Sinha, S.; Vasavi, C. S.; Waidha, K. M.; Basu, B.; Munussami, P.; Balamurali, M. M.; Doble, M.; Kumar, R. S. Bioorg. Med. Chem.2019, 27, 604.

  11. 11.

    Treshchalin, I. D.; Treshchalina, Е. M.; Shtil, A. A.; Preobrazhenskaya, M. N.; Shchekotikhin, A. E. RU Patent 2554939, 2015.

  12. 12.

    Narender, T.; Sukanya, P.; Sharma, K.; Bathula, S. R. RSC Adv.2013, 3, 6123.

  13. 13.

    Lee, C.-C.; Huang, K.-F.; Lin, P.-Y.; Huang, F.-C.; Chen, C.-L.; Chen, T.-C.; Guh, J.-H.; Lin, J.-J.; Huang, H.-S. Eur. J. Med. Chem.2012, 47, 323.

  14. 14.

    Tikhomirov, A. S.; Shtil A. A.; Shchekotikhin, A. E. Recent Pat. Anti-Cancer Drug Discovery2018, 13, 159.

  15. 15.

    Bellamy, L. New data on the Infra Red Spectra of Complex Molecules [Russian translation]; Moscow: Mir, 1971, p. 280.

  16. 16.

    Nakanishi, K. Infrared Spectra and Structure of Organic Compounds [Russian translation]; Moscow: Mir, 1965, p. 36.

  17. 17.

    Gornostaev, L. M.; Khalyavina, Y. G.; Kuznetsova, A. S.; Fominykh, O. I.; Tropina, D. A.; Murashova, E. V.; Zamilatskov, I. A. Chernyshev, V. V. Russ. J. Org. Chem.2016, 52, 80. [Zh. Org. Khim.2016, 52, 87.]

  18. 18.

    Chernyshev, V. V. Russ. Chem. Bull., Int. Ed.2001, 50, 2273. [Izv. AN, Ser. khim.2001, 2171.]

  19. 19.

    David, W. I. F.; Shankland, K. Acta Crystallogr., Sect. A2008, A64, 52.

  20. 20.

    Harris, K. D. M. Top. Curr. Chem.2012, 315, 133.

  21. 21.

    Werner, P.-E.; Eriksson, L.; Westdahl, M. J. Appl. Crystallogr.1985, 18, 367.

  22. 22.

    Visser, J. W. J. Appl. Crystallogr.1969, 2, 89.

  23. 23.

    Zlokazov, V. B. J. Appl. Crystallogr.1992, 25, 69.

  24. 24.

    Zlokazov, V. B. Comput. Phys. Commun. 1995, 85, 415.

  25. 25.

    Zhukov, S. G.; Chernyshev, V. V.; Babaev, E. V.; Sonneveld, E. J.; Schenk, H. Z. Kristallogr. 2001, 216, 5.

  26. 26.

    Zlokazov, V. B.; Chernyshev, V. V. J. Appl. Crystallogr. 1992, 25, 447.

  27. 27.

    Spek, A. L. Acta Crystallogr., Sect. D2009, D65, 148.

  28. 28.

    Groom, C. R.; Allen, F. H. Angew. Chem., Int. Ed.2014, 53, 662.

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Correspondence to Leonid M. Gornostaev.

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Gornostaev, L.M., Fominykh, O.I., Rukovets, T.A. et al. Synthesis of 6b,11b-dihydroxy-12-methylphenyl-11b,12-dihydrobenzo- [g]indeno[1,2-b]indole-5,6,7(6bH)-triones and 2-(3-hydroxy- 4,9-dioxo-4,9-dihydro-1H-benzo[f]indol-2-yl)benzamides, their structure and antiproliferative activity. Chem Heterocycl Comp (2020). https://doi.org/10.1007/s10593-020-02621-8

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Keywords

  • 2-alkylamino-1,4-naphthoquinones
  • 4-arylamino-1,2-naphthoquinones
  • 2-(3-hydroxy-4,9-dioxo-4,9-dihydro-1H-benzo[f]- indol-2-yl)benzamides
  • 2,2-dihydroxy-1,3-indanedione
  • 6b,11b-dihydroxy-12-methylphenyl-11b,12-dihydrobenzo[g]indeno[1,2-b]- indole-5,6,7(6bH)triones