Skip to main content
Log in

Cytotoxic Activity of Perfluoroalkyl-Substituted Imidazoindazoles and Imidazobenzisoxazoles

  • SEARCH FOR NEW DRUGS
  • Published:
Pharmaceutical Chemistry Journal Aims and scope

The cytotoxic activity of perfluoroalkyl imidazoindazoles and imidazobenzisoxazoles with respect to MCF-7 (human breast carcinoma) and HepG2 cell lines (human hepatocellular carcinoma) was studied. The imidazoindazoles exhibited significant cytotoxicity against MCF-7 and HepG2 cell lines. 2,6-bis(4-Fluorophenyl)-4,4-dimethyl-8-trifluoromethyl-3,4,5,6-tetrahydroimidazo[4,5-e]indazole displayed the most pronounced cytotoxic action. Regioisomeric imidazobenzisoxazoles inhibited extensively growth of HepG2 cells. The mechanism of cytotoxic action can be related to the induction of apoptosis as a result of disruption of the cell cycle, in particular, arrest of HepG2 cells in the G2 phase and MCF-7 cells in the G1 phase.

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.
Fig. 2.
Fig. 3.

Similar content being viewed by others

References

  1. M. Gaba and C. Mohan, Med. Chem. Res., 25(2), 173 – 210 (2016).

    Article  CAS  Google Scholar 

  2. A. Kanwal, F. A. Saddique, S. Aslam, et al., Pharm. Chem. J., 51(12), 1068 – 1077 (2017).

    Article  Google Scholar 

  3. I. Denya, S. F. Malan, and J. Joubert, Expert Opin. Ther. Pat., 28(6), 441 – 453 (2018).

    Article  CAS  Google Scholar 

  4. D. D. Gaikwad, A. D. Chapolikar, C. G. Devkate, et al., Eur. J. Med. Chem., 90, 707 – 731 (2015).

    Article  CAS  Google Scholar 

  5. J. Zhu, J. Mo, H-Z. Lin, et al., Bioorg. Med. Chem., 26(12), 3065 – 3075 (2018).

    Article  CAS  Google Scholar 

  6. K. P. Rakesh, C. S. Shantharam, M. B. Sridhara, et al., Med. Chem. Commun., 8(11), 2023 – 2039 (2017).

    Article  CAS  Google Scholar 

  7. Yu Zhou, J. Wang, Z. Gu, et al., Chem. Rev., 116(2), 422 – 518 (2016).

  8. V. G. Isakova, T. S. Khlebnikova, and F. A. Lakhvich, Usp. Khim., 79(10), 929 – 960 (2010); Russ. Chem. Rev., 79(10), 849 – 879 (2010).

  9. L. V. Politanskaya, G. A. Selivanova, E. V. Panteleeva, et al., Usp. Khim., 88(5), 425 – 569 (2019); Russ. Chem. Rev., 88(5), 425 – 569 (2019).

  10. T. S. Khlebnikova, Yu. A. Piven’, V. G. Zinovich, et al., Khim.- farm. Zh., 54(7), 21 – 26 (2020); Pharm. Chem. J., 54(7), 700 – 706 (2020).

  11. T. S. Khlebnikova, V. G. Isakova, A. V. Baranovskii, and F. A. Lakhvich, Zh. Obshch. Khim., 78(10), 1718 – 1727 (2008); Russ. J. Gen. Chem., 78(10), 1954 – 1963 (2008).

  12. T. S. Khlebnikova, Yu. A. Piven’, A. V. Baranovskii, and F. A. Lakhvich, Zh. Org. Khim., 49(3), 433 – 439 (2013); Russ. J. Org. Chem., 49(3), 421 – 427 (2013).

  13. T. S. Khlebnicova, Yu. A. Piven’, V. G. Isakova, et al., J. Heterocycl. Chem., 55(7), 1791 – 1797 (2018).

  14. T. S. Khlebnikova, V. G. Isakova, Yu. A. Piven’, et al., Zh. Obshch. Khim., 90(4), 637 – 641 (2020); Russ. J. Gen. Chem., 90(4), 746 – 749 (2020).

  15. J. van Meerloo, G. J. Kaspers, and J. Cloos, Methods Mol. Biol., 731, 237 – 245 (2011).

    Article  Google Scholar 

  16. O. V. Panibrat, V. N. Zhabinskii, and V. A. Khripach, Dokl. Nats. Akad. Nauk Belarusi, 63(4), 437 – 444 (2019).

    Article  Google Scholar 

  17. S. A. Mirmalek, M. A. Azizi, E. Jangholi, et al., Cancer Cell Int., 16, Art. No. 3, 1 – 9 (2016); doi: 10.1186/ s12935-016- 0279-4.

  18. R. U. Khabriev (ed.), Handbook for Experimental (Preclinical) Studies of New Drugs [in Russian], Meditsina, Moscow (2005).

    Google Scholar 

  19. G. H. Williams and K. Stoeber, J. Pathol., 226(6), 352 – 364 (2012).

    Article  CAS  Google Scholar 

  20. A. Lombardi Borgia, M. Ciomei, et al., US Pat. 9,597,317 B2, Mar. 21, 2017.

  21. GOST 12.1.007–76, Noxious substances. Classification and general safety requirements.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to T. S. Khlebnikova.

Additional information

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 55, No. 3, pp. 10 – 14, March, 2021.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khlebnikova, T.S., Panibrat, O.V., Piven, Y.A. et al. Cytotoxic Activity of Perfluoroalkyl-Substituted Imidazoindazoles and Imidazobenzisoxazoles. Pharm Chem J 55, 219–223 (2021). https://doi.org/10.1007/s11094-021-02401-4

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-021-02401-4

Keywords

Navigation