Skip to main content
SpringerLink
Log in

Synthesis and Antiproliferative Activity Evaluation of Aryl(Hetaryl)Cyclopentenone Analogs of Combretastatin A-4

Pharmaceutical Chemistry Journal Aims and scope

Cite this article

A series of previously unreported di- and triaryl(hetaryl)cyclopentenone derivatives were prepared using a convenient synthetic method and screened preliminarily for antitumor activity in four human cell lines, i.e., T-cell leukemia (Jurkat), lung adenocarcinoma (A-549), colon cancer (HCT-116), and breast adenocarcinoma (MCF-7). The most cytotoxic of the tested compounds was 2-(3,4,5-trimethoxyphenyl)-3-(4-methoxyphenyl) cyclopent-2-en-1-one. However, it was inactive against lymphocytic leukemia P388 in mice despite its cytotoxicity in in vitro tests.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

References

  1. B. Stewart and C. P. Wild (eds.), World Cancer Report 2014, WHO Press, (2014).

  2. S. Nussbaumer, P. Bonnabry, J.-L. Veuthey, and S. Fleury-Souverain, Talanta, 85(5), 2265 – 2289 (2011).

    Article  CAS  PubMed  Google Scholar 

  3. R. H. Bradbury (ed.), “Cancer,” in: Topics in Medicinal Chemistry, Vol. 1, Springer-Verlag, Berlin, Heidelberg (2007).

  4. J. H. Atkins and L. J. Gershell, Nat. Rev. Drug Discovery, 1(7), 491 – 492 (2002).

    Article  CAS  PubMed  Google Scholar 

  5. E. A. Perez, Mol. Cancer Ther., 8(8), 2086 – 2095 (2009).

    Article  CAS  PubMed  Google Scholar 

  6. C. Dumontet and M. A. Jordan, Nat. Rev. Drug Discovery, 9(10), 790 – 803 (2010).

    Article  CAS  PubMed  Google Scholar 

  7. C. Avendano and J. C. Menendez, Medicinal Chemistry of Anticancer Drugs, Chap. 8, (2008), p. 229.

    Google Scholar 

  8. G. C. Tron, T. Pirali, G. Sorba, et al, J. Med. Chem., 49(11), 3033 – 3044 (2006).

    Article  CAS  PubMed  Google Scholar 

  9. A. Nagle, W. Hur, and N. S. Gray, Curr. Drug Targets, 7(3), 305 – 306 (2006).

    Article  CAS  PubMed  Google Scholar 

  10. T. Brown, H. Holt, and M. Lee, Top. Heterocycl. Chem., 2, 1 (2006).

    CAS  Google Scholar 

  11. A. Cirla and J. Mann, Nat. Prod. Rep., 20(6), 558 – 564 (2003).

    Article  CAS  PubMed  Google Scholar 

  12. D. J. Chaplin, G. R. Pettit, C. S. Parkins, and A. S. Hill, Br. J. Cancer Suppl., 74, S86-S88 (1996).

    Article  CAS  Google Scholar 

  13. G. Nagaiah and S. C. Remick, Future Oncol., 6(8), 1219 – 1228 (2010).

    Article  CAS  PubMed  Google Scholar 

  14. N.-H. Nam, Y. Kim, Y.-J. You, D.-H. Hong, et al., Bioorg. Med. Chem., 11, 1021 – 1029 (2003).

    Article  CAS  PubMed  Google Scholar 

  15. K. Oshumi, R. Nakagawa, Y. Fukuda, et al., J. Med. Chem., 41(16), 3022 – 3032 (1998).

    Article  Google Scholar 

  16. K. Gaukroger, J. A. Hadfield, N. J. Lawrence, et al., Org. Biomol. Chem., 1, 3033 – 3037 (2003).

    Article  CAS  PubMed  Google Scholar 

  17. J. M. Andreu, B. Perez-Ramirez, M. J. Gorbunoff, et al., Biochemistry, 37(23), 8356 – 8368 (1998).

    Article  CAS  PubMed  Google Scholar 

  18. N.-H. Nam, Y. Kim, Y.-J. You, et al., Bioorg. Med. Chem. Lett., 12(15), 1955 – 1958 (2002).

    Article  CAS  PubMed  Google Scholar 

  19. M. K. Gurjar, R. D. Wakharkar, et al., USA Pat. Appl. No. 0229146 (2003); Chem. Abstr., 140, 16528 (2003).

  20. M. K. Gurjar, R. D. Wakharkar, et al., Indian Pat. Appl. No. 2005DE00723 (2006); Chem. Abstr., 147, 406939 (2007).

  21. G. R. Pettit, S. B. Singh, M. R. Boyd, et al, J. Med. Chem., 38(10), 1666 – 1672 (1995).

    Article  CAS  PubMed  Google Scholar 

  22. V. Z. Shirinian, A. A. Shimkin, D. V. Lonshakov, et al., J. Photochem. Photobiol., A, 233, 1 – 14 (2012).

    Article  CAS  Google Scholar 

  23. V. Z. Shirinian, D. V. Lonshakov, A. G. Lvov, et al., Photochem. Photobiol. Sci., 12, 1717 – 1725 (2013).

    Article  CAS  PubMed  Google Scholar 

  24. V. Z. Shirinian, D. V. Lonshakov, V. V. Kachala, et al., J. Org. Chem., 77, 8112 – 8123 (2012).

    Article  CAS  PubMed  Google Scholar 

  25. A. A. Shimkin, V. Z. Shirinian, A. K. Mailian, et al., Russ. Chem. Bull., Int. Ed., 60(1), 139 – 142 (2011).

    Article  CAS  Google Scholar 

  26. V. Z. Shirinian, A. G. Lvov, A. M. Yanina, et al., Chem. Heterocycl. Compd., 51(3), 234 – 241 (2015); Khim. Geterotsikl. Soedin., 51(3), 234 – 241 (2015).

  27. D. V. Lonshakov, V. Z. Shirinian, and A. G. Lvov, Mendeleev Commun., 23, 268 – 270 (2013).

    Article  CAS  Google Scholar 

  28. N.-H. Nam, Y. Kim, Y.-J. You, et al., Arch. Pharm. Res., 25(5), 600 – 607 (2002).

    Article  CAS  PubMed  Google Scholar 

  29. A. G. Lvov, V. Z. Shirinian, A. M. Kavun, Mendeleev Commun., 24, 277 – 279 (2014).

    Article  CAS  Google Scholar 

  30. V. Z. Shirinian, A. G. Lvov, E. Yu. Bulich, et al., Tetrahedron Lett., 56, 5477 – 5480 (2015).

    Article  CAS  Google Scholar 

  31. A. Van de Loosdrecht, R. H. J. Beelen, G. J. Ossenkoppele, et al., J. Immunol. Methods, 174, 311 – 320 (1994).

    Article  PubMed  Google Scholar 

  32. Methodical Recommendations for Preclinical Studies of Drug Antitumor Activity. Handbook for Preclinical Drug Trials [in Russian], Part 1, Grif i K, Moscow (2012), pp. 642 – 656.

Download references

Acknowledgments

The work was sponsored by the Russian Foundation for Basic Research (Grant 15 – 53 – 05049) and the Ministry of Education and Science of the Republic of Armenia (Grant 15RF-046) under collaborative science programs.

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninskii Prosp, Moscow, 119991, Russia

    V. Z. Shirinyan & A. G. L’vov

  2. Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, 26 Azatutyan Pr., 0014, 375014, Yerevan, Armenia

    A. I. Markosyan & S. A. Gabrielyan

  3. N. N. Blokhin Russian Cancer Research Center, Russian Academy of Medical Sciences, 23 Kashirskoe Shosse, Moscow, 115478, Russia

    M. A. Baryshnikova

  4. D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Pl., Moscow, 125047, Russia

    L. V. Yaminova

Authors
  1. V. Z. Shirinyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. I. Markosyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. A. Baryshnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. L. V. Yaminova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. G. L’vov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. A. Gabrielyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. Z. Shirinyan.

Additional information

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 51, No. 10, pp. 16 – 21, October, 2017.

Rights and permissions

Reprints and Permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shirinyan, V.Z., Markosyan, A.I., Baryshnikova, M.A. et al. Synthesis and Antiproliferative Activity Evaluation of Aryl(Hetaryl)Cyclopentenone Analogs of Combretastatin A-4. Pharm Chem J 51, 867–872 (2018). https://doi.org/10.1007/s11094-018-1706-8

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-018-1706-8

Keywords

search

Navigation