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Heterocyclic Analogs of 5,12-Naphthacenequinone 14*. Synthesis of naphtho[2,3-f]indole-3-carboxylic Acid Derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

3-carboxylate by using vicarious substitution of hydrogen, followed by intramolecular reductive heterocyclization. Some chemical properties of the target compound were characterized. As observed for the first time in the series of linear hetaryl-fused anthraquinones, the alkylation of hydroxy groups in naphtho[2,3-f]indole-5,10-diones gave not only 4,11-dialkoxy derivatives, but also the isomeric 5,10-dialkoxy derivatives of naphtho[2,3-f]indole-4,11-dione.

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References

  1. Tikhomirov, A. S.; Bykov, E. E.; Luzikov Y. N.; Korolev, A. M.; Shchekotikhin, A. E. Chem. Heterocycl. Compd. 2016, 52, 797. [Khim. Geterotsikl. Soedin. 2016, 52, 797.]

  2. Tikhomirov, A. S.; Shchekotikhin, A. E.; Lee, Y.-H.; Chen, Y.-A.; Yeh, C.-A. Tatarskiy, V. V.; Dezhenkova, L. G.; Glazunova, V. A.; Balzarini, J.; Shtil, A. A.; Preobrazhenskaya, M. N.; Chueh, P. J. J. Med. Chem. 2015, 58, 9522.

    Article  CAS  Google Scholar 

  3. Lee, Y. R.; Chen, T. C.; Lee, C. C.; Chen, C.-L.; Ali, A. A.; Tikhomirov, A. S.; Guh, J.-H.; Yu, D.-S.; Huang, H.-S. Eur. J. Med. Chem. 2015, 102, 661.

    Article  CAS  Google Scholar 

  4. Chen, W. L.; Wang, Z. H.; Feng, T. T.; Li, D. D.; Wang, C. H.; Xu, X. L.; Zhang, X. J.; You, Q. D.; Guo, X. K. Bioorg. Med. Chem. 2016, 24, 6102.

    Article  CAS  Google Scholar 

  5. Mani, T.; Wang, F.; Knabe, W. E.; Sinn, A. L.; Khanna, M.; Jo, I.; Sandusky, G. E.; Sledge, G. W.; Jones, D. R.; Khanna, R.; Pollok, K.; Meroueh, S. O. Bioorg. Med. Chem. 2013, 21, 2145.

    Article  CAS  Google Scholar 

  6. Shchekotikhin, A. E.; Dezhenkova, L. G.; Tsvetkov, V. B.; Luzikov, Y. N.; Volodina, Y. L.; Tatarskiy, V. V.; Kalinina, A. A.; Treshalin, M. I.; Treshalina, H. M.; Romanenko, V. I.; Kaluzhny, D. N.; Kubbutat, M.; Schols, D.; Pommier, Y.; Shtil, A. A.; Preobrazhenskaya, M. N. Eur. J. Med. Chem. 2016, 112, 114.

    Article  CAS  Google Scholar 

  7. Khoumeri, O.; Giuglio-Tonolo, G.; Crozet, M. D.; Terme, T.; Vanelle, P. Tetrahedron 2011, 67, 6173.

    Article  CAS  Google Scholar 

  8. Shchekotikhin, A. E.; Glazunova, V. A.; Dezhenkova, L. G.; Luzikov, Y. N.; Buyanov, V. N.; Treshalina, H. M.; Lesnaya, N. A.; Romanenko, V. I.; Kaluzhny, D. N.; Balzarini, J.; Agama, K.; Pommier, Y.; Shtil, A. A.; Preobrazhenskaya, M. N. Eur. J. Med. Chem. 2014, 86, 797.

    Article  CAS  Google Scholar 

  9. Shchekotikhin, A. E.; Dezhenkova, L. G.; Susova, O. Y.; Glazunova, V. A.; Luzikov, Y. N.; Sinkevich, Y. B.; Buyanov, V. N.; Shtil, A. A.; Preobrazhenskaya, M. N. Bioorg. Med. Chem. 2007, 15, 2651.

    Article  CAS  Google Scholar 

  10. Shchekotikhin, A. E. Heterocyclic Analogs of 5,12-Naphthacenequinone. Synthesis, Chemical Properties, and Biological Activity [in Russian]; Lambert Academic Publishing, 2011, p. 500.

  11. Taber, D. F.; Tirunahari, P. K. Tetrahedron 2011, 67, 7195.

    Article  CAS  Google Scholar 

  12. Attar, K.; Camara, H. D.; Benchidmi, М.; Essassi, E. M.; Pierrot, М. Heterocycl. Commun. 2003, 9, 373.

    Article  CAS  Google Scholar 

  13. Gallou, F.; Yee, N.; Qiu, F.; Senanayake, C.; Linz, G.; Schnaubelt, J.; Soyka, R. Synlett 2004, 883.

  14. Nor, S. M. M.; Sukari, M. A. H. M.; Azziz, S. S. S. A.; Fah, W. C.; Alimon, H.; Juhan, S. F. Molecules 2013, 18, 8046.

    Article  CAS  Google Scholar 

  15. Gorelik, M. V.; Mishina, E. V. Zh. Org. Khim. 1983, 19, 2185.

    CAS  Google Scholar 

  16. Ahmad, R.; Jeinie, M. F.; Ismail, N. H.; Hazni, H.; Ng, S. W. Acta Crystallogr., Sect. E.: Crystallogr. Commun. 2011, E67, o1144.

    Article  Google Scholar 

  17. Chemistry of Anthraquinones and their Derivatives [in Russian]; Gorelik, M. V., Ed.; Khimiya: Moscow, 1983, p. 182.

  18. Silverstain, R. M.; Webster, F. X.; Kiemle, D. J. Spectrometric Identification of Organic Compounds; John Wiley & Sons, 2005, 7th ed., p. 502.

  19. Mąkosza, M.; Wojciechowski, K. Chem. Heterocycl. Compd. 2015, 51, 210. [Khim. Geterotsikl. Soedin. 2015, 51, 210.]

  20. Mąkosza, M.; Wojciechowski, K. In Topics in Heterocyclyc. Chemistry: Metal Free CH Functionalization of Aromatics; Charushin, V.; Chupakhin, O., Eds.; Springer, 2014, Vol. 37, p. 51.

  21. Lee, J.-Ch.; Bae, Y.-H.; Chang, S.-K. Bull. Korean Chem. Soc. 2003, 24, 407.

    Article  CAS  Google Scholar 

  22. Pfaendler, H. R.; Weisner, F. Heterocycles 1995, 40, 717.

    Article  CAS  Google Scholar 

  23. Shalem, H.; Shatzmiller, S.; Feit, B.-A. Liebigs Ann. 1995, 2, 433.

    Article  Google Scholar 

  24. Schaefer, H.; Seebach, D. Tetrahedron 1995, 51, 2305.

    Article  Google Scholar 

  25. Tikhomirov, A. S.; Shchekotikhin, A. E.; Luzikov, Y. N.; Korolev, A. M.; Preobrazhenskaya, M. N. Chem. Heterocycl. Compd. 2014, 50, 271. [Khim. Geterotsikl. Soedin. 2014, 298.]

  26. Wuts, P. G. M.; Green, T. W. Green's Protecting Groups Organic Synthesis; John Wiley & Sons, 2007, 5th ed., p. 886.

  27. Tikhomirov, A. S.; Shchekotikhin, A. E.; Preobrazhenskaya, M. N. Chem. Heterocycl. Compd. 2014, 50, 171. [Khim. Geterotsikl. Soedin. 2014, 193.]

  28. Sinkevich, Yu. B.; Shchekotikhin, A. E.; Luzikov, Yu. N.; Buyanov, V. N.; Kovalenko, L. V. Chem. Heterocycl. Compd. 2007, 43, 1252. [Khim. Geterotsikl. Soedin. 2007, 1478.]

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Correspondence to Andrey E. Shchekotikhin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(10), 1072–1079

* For Communication 13, see1.

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Tikhomirov, A.S., Litvinova, V.A., Luzikov, Y.N. et al. Heterocyclic Analogs of 5,12-Naphthacenequinone 14*. Synthesis of naphtho[2,3-f]indole-3-carboxylic Acid Derivatives. Chem Heterocycl Comp 53, 1072–1079 (2017). https://doi.org/10.1007/s10593-017-2173-y

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  • DOI: https://doi.org/10.1007/s10593-017-2173-y

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