Skip to main content
SpringerLink
Log in

Synthesis and In vitro Study of Cytotoxic Activity of New Tetrazole-Containing 2,4-Diamino-1,3,5-triazine Derivatives

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

New tetrazole-containing derivatives of 2,4-diamino-1,3,5-triazine were synthesized. The cytotoxic activity of the obtained compounds against Huh-7 and HeLa tumor cell lines was studied by the MTT test. The most significant antitumor activity was shown by 1,3,5-triazines containing a 5-phenyltetrazol-2-ylacetohydrazide fragment. The resulting compounds showed practically no cytotoxic effect on non-tumor cells of the human embryonic kidney line HEK293.

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

Scheme
Scheme
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Singh, S., Mandal, M.K., Masih, A., Saha, A., Ghosh, S.K., Bhat, H.R., and Singh, U.P., Arch. Pharm., 2021, vol. 354, no. 6, article no. 2000363. https://doi.org/10.1002/ardp.202000363

  2. Singla, P., Luxami, V., and Paul, K., Eur. J. Med. Chem., 2015, vol. 102, p. 39. https://doi.org/10.1016/j.ejmech.2015.07.037

    Article  CAS  PubMed  Google Scholar 

  3. Cascioferro, S., Parrino, B., Spanò, V., Carbone, A., Montalbano, A., Barraja, P., Diana, P., and Cirrincione, G., Eur. J. Med. Chem., 2017, vol. 142, p. 523. https://doi.org/10.1016/j.ejmech.2017.09.035

    Article  CAS  PubMed  Google Scholar 

  4. Shah, D.R., Modh, R.P., and Chikhalia, K.H., Future Med. Chem., 2014, vol. 6., no. 4, p. 463. https://doi.org/10.4155/fmc.13.212

    Article  CAS  PubMed  Google Scholar 

  5. Sonawane, R.P., Sikervar, V., and Sasmal, S., Compr. Heterocycl. Chem., 2022, vol. 9, p. 181. https://doi.org/10.1016/B978-0-12-818655-8.00018-4

    Article  Google Scholar 

  6. Maliszewski, D. and Drozdowska, D., Pharmaceuticals, 2022, vol. 15, no. 2, p. 221. https://doi.org/10.3390/ph15020221

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Hiebel, M.-A. and Suzenet, F., Progr. Heterocycl. Chem., 2021, vol. 33, p. 441. https://doi.org/10.1016/B978-0-323-98410-2.00014-X

    Article  CAS  Google Scholar 

  8. Hu, J., Zhang, Y., Tang, N., Lu, Y., Guo, P., and Huang, Z., Bioorg. Med. Chem., 2021, vol. 32, article no. 115997. https://doi.org/10.1016/j.bmc.2021.115997

  9. Pratt, W.B. and Ruddon, R.W., The Anticancer Drugs, New York: Oxford University Press, 1979.

  10. Krętowski, R., Drozdowska, D., Kolesińska, B., Kamiński, Z., Frączyk, J., and Cechowska-Pasko, M., Invest. New Drugs, 2019, vol. 37, no. 5, p. 984. https://doi.org/10.1007/s10637-018-0712-8

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Rageot, D., Bohnacker, T., Melone, A., Langlois, J.-B., Borsari, C., Hillmann, P., Sele, A.M., Beaufils, F., Zvelebil, M., Hebeisen, P., Löscher, W., Burke, J., Doriano Fabbro, D., and Wymann, M.P., J. Med. Chem., 2018, vol. 61, no. 22, p. 10084. https://doi.org/10.1021/acs.jmedchem.8b01262

    Article  CAS  PubMed  Google Scholar 

  12. Beaufils, F., Cmiljanovic, N., Cmiljanovic, V., Bohnacker, T., Melone, A., Marone, R., Jackson, E., Zhang, X., Sele, A., Borsari, C., Mestan, J., Hebeisen, P., Hillmann, P., Giese, B., Zvelebil, M., Fabbro, D., Williams, R.L., Rageot, D., and Wymann, M.P., J. Med. Chem., 2017, vol. 60, no. 17, p. 7524. https://doi.org/10.1021/acs.jmedchem.7b00930

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Prasher, P., Sharma, M., Aljabali, A.A.A., Gupta, G., Negi, P., Kapoor, D.N., Singh, I., Zacconi, F.C., Pinto, T.J.A., da Silva, M.W., Bakshi, H.A., Chellappan, D.K., Tambuwala, M.M., and Dua, K., Drug Dev. Res., 2020, vol. 81, no. 7, p. 837. https://doi.org/10.1002/ddr.21704

    Article  CAS  PubMed  Google Scholar 

  14. Guo, H. and Diao, Q.-P., Curr. Top. Med. Chem., 2020, vol. 20, no. 16, p. 1481. https://doi.org/10.2174/1568026620666200310122741

    Article  CAS  PubMed  Google Scholar 

  15. Popova, E.A., Trifonov, R.E., and Ostrovskii, V.A., Russ. Chem. Rev., 2019, vol. 88, p. 644. https://doi.org/10.1070/RCR4864

    Article  CAS  Google Scholar 

  16. Ostrovskii, V.A., Trifonov, R.E., and Popova, E.A., Russ. Chem. Bull., 2012, vol. 61, no. 4, p. 768. https://doi.org/10.1007/s11172-012-0108-4

    Article  CAS  Google Scholar 

  17. Ostrovskii, V.A., Popova, E.A., and Trifonov, R.E., Compr. Heterocycl. Chem., 2022, p. 182. https://doi.org/10.1016/B978-0-12-818655-8.00131-1

  18. Herr, R.J., Bioorg. Med. Chem., 2002, vol. 10, no. 11, p. 3379. https://doi.org/10.1016/S0968-0896(02)00239-0

    Article  CAS  PubMed  Google Scholar 

  19. Popova, E.A., Protas, A.V., and Trifonov, R.E., AntiCancer Agents Med. Chem., 2017, vol. 17, no. 14, p. 1856. https://doi.org/10.2174/1871520617666170327143148

    Article  CAS  Google Scholar 

  20. Ostrovskii, V.A., Popova, E.A., and Trifonov, R.E., Adv. Heterocycl. Chem., 2017, vol. 123, p. 1. https://doi.org/10.1016/bs.aihch.2016.12.003

    Article  CAS  Google Scholar 

  21. Popova, E.A. and Trifonov, R.E., Russ. Chem. Rev., 2015, vol. 84, no. 9, p. 891. https://doi.org/10.1070/RCR4527

    Article  CAS  Google Scholar 

  22. Mikolaichuk, O.V., Sharoyko, V.V., Popova, E.A., Protas, A.V., Fonin, A.V., Anufrikov, Y.A., Malkova, A.M., Shmaneva, N.T., Ostrovskii, V.A., and Semenov, K.N., Russ. Chem. Bull., 2022, vol. 71, no. 5, p. 1050. https://doi.org/10.1007/s11172-022-3507-1

    Article  CAS  Google Scholar 

  23. Blotny, G., Tetrahedron, 2006, vol. 62, no. 41, p. 9507. https://doi.org/10.1016/j.tet.2006.07.039

    Article  CAS  Google Scholar 

  24. Ostrovskii, V.А., Danagulyan, G.G., Nesterova, O.M., Pavlyukova, Y.N., Tolstyakov, V.V., Zarubina, O.S., Slepukhin, P.А., Esaulkova, Y.L., Muryleva, A.А., Zarubaev, V.V., and Trifonov, R.E., Chem. Heterocycl. Compd., 2021, vol. 57, no. 4, p. 448. https://doi.org/10.1007/s10593-021-02922-6

    Article  CAS  Google Scholar 

  25. Putis, S.M., Zubarev, V.Y., Poplavskii, V.S., and Ostrovskii, V.A., Chem. Heterocycl. Compd., 2001, no. 6, p. 759. https://doi.org/10.1023/A:1011909127876

    Article  Google Scholar 

  26. Vereshchagin, L.I., Verkhozina, O.N., Pokatilov, F.A., Proidakov, A.G., and Kizhnyaev, V.N., Chem. Heterocycl. Compd., 2010, vol. 46, no. 2, p. 206. https://doi.org/10.1007/s10593-010-0493-2

    Article  CAS  Google Scholar 

  27. Mikolaichuk, O.V., Popova, E.A., Protas, A.V., Rakipov, I.T., Nerukh, D.A., Petrov, A.V., Charykov, N.A., Ageev, S.V., Tochilnikov, G.V., Zmitrichenko, I.G., Stukov, A.N., Semenov, K.N., and Sharoyko, V.V., J. Mol. Liq., 2022, vol. 356, article no. 119043. https://doi.org/10.1016/j.molliq.2022.119043

Download references

ACKNOWLEDGMENTS

The authors are grateful to the Resource Centers of St. Petersburg State University “Magnetic Resonance Research Center,” “Chemical Analysis and Materials Research Center,” and “Center for Thermogravimetric and Calorimetric Research.”

Funding

This work was financially supported by the Ministry of Health of the Russian Federation (government task on the topic “Creation and evaluation of the antitumor activity of conjugates of non-annulated 1,3,5-triazinyl-tetrazoles with targeted delivery molecules to microenvironment tumor cells targets”).

Author information

Authors and Affiliations

  1. I.P. Pavlov First St. Petersburg State Medical University, 197022, St. Petersburg, Russia

    O. V. Mikolaichuk, A. V. Protas, E. A. Popova, V. V. Sharoyko & K. N. Semenov

  2. St. Petersburg State University, 199034, St. Petersburg, Russia

    O. V. Mikolaichuk, V. V. Sharoyko & K. N. Semenov

  3. A. M. Granov Russian Scientific Center of Radiology and Surgical Technologies, 197758, St. Petersburg, Russia

    O. V. Mikolaichuk, A. V. Protas, E. A. Popova, O. E. Molchanov, D. N. Maistrenko, V. V. Sharoyko & K. N. Semenov

  4. St. Petersburg State Institute of Technology (Technical University), 190013, St. Petersburg, Russia

    V. A. Ostrovskii & Yu. N. Pavlyukova

Authors
  1. O. V. Mikolaichuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Protas
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. A. Popova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. E. Molchanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. D. N. Maistrenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. A. Ostrovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yu. N. Pavlyukova
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. V. V. Sharoyko
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. K. N. Semenov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to O. V. Mikolaichuk.

Ethics declarations

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mikolaichuk, O.V., Protas, A.V., Popova, E.A. et al. Synthesis and In vitro Study of Cytotoxic Activity of New Tetrazole-Containing 2,4-Diamino-1,3,5-triazine Derivatives. Russ J Gen Chem 92, 1621–1628 (2022). https://doi.org/10.1134/S1070363222090055

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363222090055

Keywords:

Search

Navigation