Skip to main content
Log in

The Synthesis and Cytotoxic Properties of Selenopheno[3,2-c]- and Selenopheno-[2,3-c]quinolones*

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

We have developed a method for the synthesis of novel selenophene-containing polycyclic heterocycles, derivatives of selenopheno[3,2-c]- and selenopheno[2,3-c]quinolones. The cytotoxic activity of these compounds was studied in vitro. The molecular structure of 3-bromo-5-methyl-2-(piperidin-2-ylmethyl)selenopheno[3,2-c]quinolin-4(5H)-one was confirmed by X-ray analysis.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1

Similar content being viewed by others

References

  1. V. Gressler, C. Z. Stüker, G. de O. C. Dias, I. I. Dalcol, R. A. Burrow, J. Schmidt, L. Wessjohann, and A. F. Morel, Phytochemistry, 69, 994 (2008).

    Article  CAS  Google Scholar 

  2. T. Sripisut, T. Ritthiwigrom, T. Promgool, K. Yossathera, S. Deachathai, W. Phakhodee, S. Cheenpracha, and S. Laphookhieo, Phytochem. Lett., 5, 379 (2012).

    Article  CAS  Google Scholar 

  3. A. Gafter-Gvili, A. Fraser, M. Paul, M. D. van de Wetering, L. C. M. Kremer, and L. Leibovici, Antibiotic Prophylaxis for Bacterial Infections in Afebrile Neutropenic Patients Following Chemotherapy, Wiley Online Library (2009), DOI: 10.1002/14651858.CD004386.pub3.

  4. B. S. Jayashree, S. Thomas, and Y. Nayak, Med. Chem. Res., 19, 193 (2010).

    Article  CAS  Google Scholar 

  5. D. E. King, R. Malone, and S. H. Lilley, Am. Fam. Physician, 61, 2741 (2000).

    CAS  Google Scholar 

  6. T. Ohashi, Y. Oguro, T. Tanaka, Z. Shiokawa, S. Shibata, Y. Sato, H. Yamakawa, H. Hattori, Y. Yamamoto, S. Kondo, M. Miyamoto, H. Tojo, A. Baba, and S. Sasaki, Bioorg. Med. Chem., 20, 5496 (2012).

    Article  CAS  Google Scholar 

  7. K. Goerlitzer, B. Gabriel, P. Frohberg, I. Wobst, G. Drutkowski, J. Wiesner, and H. Jomaa, Pharmazie, 59, 439 (2004).

    CAS  Google Scholar 

  8. A. V. Polishchuk, E. T. Karaseva, M. A. Medkov, and V. E. Karasev, Proceedings of Far Eastern Division of Russ. Acad. Sci., No. 2, 128 (2005).

  9. Y.-L. Chen, US Pat. Appl. 6656949.

  10. J. E. Spallholz, Bull. Selenium-Tellurium Develop. Assoc., 1 (2001).

  11. H. Arvilommi, K. Poikonen, I. Jokinen, O. Muukkonen, L. Räsänen, J. Foreman, and J. K. Huttunen, Infect. Immun., 41, 185 (1983).

    CAS  Google Scholar 

  12. R. Bohm, Pharmazie, 42, 793 (1987).

    CAS  Google Scholar 

  13. P. Arsenyan, K. Rubina, I. Shestakova, and I. Domracheva, Eur. J. Med. Chem., 42, 635 (2007).

    Article  CAS  Google Scholar 

  14. M. S. Shahabuddin, M. Nambiar, B. Choudhary, G. M. Advirao, and S. C. Raghavan, Invest. New Drugs, 28, 35 (2010).

    Article  CAS  Google Scholar 

  15. V. Yu. Mortikov, V. P. Litvinov, A. M. Shestopalov, Yu. A. Sharanin, E. E. Apenova, G. A. Galegov, I. I. Abdullaev, T. B. Asadullaev, and F. I. Abdullaev, Khim.-Farm. Zh., 25, 5, 41 (1991). [Pharm. Chem. J., 25, 312 (1991).]

  16. S. E. Bahaie, M. G. Assy, and M. M. Hassanier, Pharmazie, 45, 791 (1990).

    Google Scholar 

  17. J. R. Hwu, L.-L. Lai, G. H. Hakimelahi, and H. Davari, Helv. Chim. Acta, 77, 1037 (1994).

    Article  CAS  Google Scholar 

  18. T. Ventslavskaia, L. Stazhadze, and V. Korzhova, Farmakol. Toksikol. (Moscow), 47, 38 (1984).

    CAS  Google Scholar 

  19. A. Kudrin and L. Zaidler, Farmakol. Toksikol. (Moscow), 31, 41 (1968).

    CAS  Google Scholar 

  20. V. G. Beylin, O. P. Goel, A. D. Sercel, and H. D. H. Showalter, US Pat. Appl. 4806654.

  21. J. Zakrzewski and M. Krawczyk, Bioorg. Med. Chem. Lett., 21, 514 (2011).

    Article  CAS  Google Scholar 

  22. S. Leycks and M. Parnham, Agents Actions, 30, 426 (1990).

  23. P. Arsenyan, I. Shestakova, K. Rubina, I. Domracheva, A. Nesterova, K. Vosele, O. Pudova, and E. Lukevics, Eur. J. Pharmacol, 465, 229 (2003).

    Article  CAS  Google Scholar 

  24. P. Arsenyan, E. Paegle, S. Belyakov, I. Shestakova, E. Jaschenko, I. Domracheva, and J. Popelis, Eur. J. Med. Chem., 46, 3434 (2011).

    Article  CAS  Google Scholar 

  25. N. C. Becknell, J. A. Lyons, L. D. Aimone, J. A. Gruner, J. R. Mathiasen, R. Raddatz, and R. L. Hudkins, Bioorg. Med. Chem. Lett., 21, 7076 (2011).

    Article  CAS  Google Scholar 

  26. Report of the International Workshop on in vitro Methods for Assembling Acute Systemic Toxicity, NIH Publication, No. 01-4499 (2001), p. 12.

  27. D. J. Fast, R. C. Lynch, and R. W. Leu, J. Leucocyt. Biol., 52, 255 (1992).

    CAS  Google Scholar 

  28. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 64, 112 (2008).

  29. S. Maskay, C. J. Gilmore, C. Edwards, N. Stewart, and K. Shankland, maXus. Computer Program for the Solution and Refinement of Crystal Structures, Bruker Nonius, MacScience, The University of Glasgow (1999).

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to P. Arsenyan.

Additional information

*Dedicated to Academician J. Stradiņš on the occasion of his 80th birthday.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1804-1811, November, 2013.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Arsenyan, P., Vasiljeva, J., Shestakova, I. et al. The Synthesis and Cytotoxic Properties of Selenopheno[3,2-c]- and Selenopheno-[2,3-c]quinolones*. Chem Heterocycl Comp 49, 1674–1680 (2014). https://doi.org/10.1007/s10593-014-1419-1

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-014-1419-1

Keywords

Navigation