Skip to main content
SpringerLink
Log in

Synthesis and properties of 5-aryl-3-diazo-3H-pyrazoles and 3-aryl-1H-pyrazole-5-diazonium salts. Preparation and cytolytic activity studies of 2-arylpyrazolo-[5,1-c][1,2,4]benzotriazines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A comparative analysis of physicochemical properties and reactivity of 3-aryl-1H-pyrazole-5-diazonium tetrafluoroborates and 5-aryl-3-diazo-3H-pyrazoles in azo coupling reactions is presented. It is shown that diazonium salts have higher reactivity compared to the respective 3-diazopyrazoles, which is in agreement with their physicochemical properties. Heterocyclization of the synthesized azo compounds provided 2-arylpyrazolo[5,1-c][1,2,4]benzotriazines, which were screened for antitumor activity against human uterine endothelium cancer cells (HeLa cell line) and human skin fibroblasts using the MTT assay and flow cytometry. It was found that all of the tested compounds exhibited moderate to high cytotoxic activity. The best results were obtained with 6,8-dimethoxy-2-phenylpyrazolo-[5,1-c][1,2,4]benzotriazine.

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

Figure 1.
Figure 2.

Similar content being viewed by others

References

  1. World Health Statistics 2017: Monitoring Health for the SDGs, Sustainable Development Goals; World Health Organization: Geneva, 2017.

  2. (a) Gouda, M. A.; Berghot, M. A.; Abd El-Ghani, Ghada E.; Khalil, A. M. Eur. J. Med. Chem. 2010, 45, 1338. (b) Mohamed, H. A.; Abdel-Wahab, B. F.; Abdel-Latif, E. J. Chem. Pharm. Res. 2015, 7, 1218.

  3. Gilligan, P. J.; Folmer, B. K.; Hartz, R. A.; Koch, S.; Nanda, K. K.; Andreuski, S.; Fitzgerald, L.; Miller, K.; Marshall, W. J. Bioorg. Med. Chem. 2003, 11, 4093.

    Article  CAS  Google Scholar 

  4. Guerrini, G.; Ciciani, G.; Costanzo, A.; Daniele, S.; Martini, C.; Ghelardini, C.; Di Cesare Mannelli, L.; Ciattini, S. Bioorg. Med. Chem. 2013, 21, 2186.

    Article  CAS  PubMed  Google Scholar 

  5. Karpenko, I.; Deev, S.; Kiselev, O.; Charushin, V.; Rusinov, V.; Ulomsky, E.; Deeva, E.; Yanvarev, D.; Ivanov, A.; Smirnova, O.; Kochetkov, S.; Chupakhin, O.; Kukhanova, M. Antimicrob. Agents Chemother. 2010, 54, 2017.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Ciciani, G.; Coronnello, M.; Guerrini, G.; Selleri, S.; Cantore, M.; Failli, P.; Mini, E.; Costanzo, A. Bioorg. Med. Chem. 2008, 16, 9409.

    Article  CAS  PubMed  Google Scholar 

  7. (a) Tišler, M.; Stanovnik, B. Chem. Heterocycl. Compd. 1980, 16, 443. [Khim. Geterotsikl. Soedin. 1980, 579.] (b) Cirrincione, G.; Almerico, A. M.; Aiello, E.; Dattolo, G. Adv. Heterocycl. Chem. 1990, 48, 65. b Ledenyova, I. V.; Didenko, V. V.; Shikhaliev, Kh. S. Chem. Heterocycl. Compd. 2014, 50, 1214. [Khim. Geterotsikl. Soedin. 2014, 1318.]

  8. Sadchikova, E. V.; Mokrushin, V. S. Rus. Chem. Bull., Int. Ed. 2003, 52, 1600. [Izv. Akad. Nauk, Ser. Khim. 2003, 1516.]

  9. Sadchikova, E. V.; Mokrushin, V. S. Rus. Chem. Bull., Int. Ed. 2005, 54, 354. [Izv. Akad. Nauk, Ser. Khim. 2005, 348.]

  10. Magee, W. L.; Rao, C. B.; Glinka, J.; Hui, H.; Amick, T. J.; Fiscus, D.; Kakodkar, S.; Nair, M.; Shechter, H. J. Org. Chem. 1987, 52, 5538.

    Article  CAS  Google Scholar 

  11. Pretsch, E.; Bühlmann, P.; Affolter, C. Structure Determination of Organic Compounds. Tables of Spectral Data; Springer-Verlag: Berlin, 2000, p. 104, 186.

  12. (a) Mokrushin, V. S.; Selezneva, I. S.; Pospelova, T. A.; Usova, V. K. Chem. Heterocycl. Compd. 1997, 33, 1086. [Khim. Geterotsikl. Soedin. 1997, 1245.] (b) Sadchikova, E. V.; Mokrushin, V. S.; Pospelova, T. A.; Selezneva, I. S. Chem. Heterocycl. Compd. 1999, 35, 176. [Khim. Geterotsikl. Soedin. 1999, 199.]

  13. Chemistry of Heterocyclic Diazo Compounds [in Russian]; Mokrushin, V. S.; Sadchikova, E. V., Eds.; Prospekt Nauki: St. Petersburg, 2013.

  14. (a) Bamberger, E. Ber. Dtsch. Chem. Ges. 1899, 32, 1773. (b) Reimlinger, H.; van Overstraeten, A. Chem. Ber. 1966, 99, 3350.

  15. (a) Leban, I.; Stanovnik, B.; Tišler, M. Acta Crystallogr., Sect. B: Struct. Sci., Cryst. Eng. Mater. 1978, B34, 293. (b) Almerico, A. M.; Cirrincione, G.; Aiello, E.; Dattolo, G. Farmaco Sci. 1988, 43, 1047. (c) Daidone, G.; Maggio, B.; Raimondi, M. V.; Bombieri, G.; Marchini, N.; Artali, R. Heterocycles 2005, 65, 2753. (d) Parrish, D. A.; Kramer, S.; Windler, G. K.; Chavez, D. E.; Leonard, P. W. Acta Crystallogr., Sect. E: Crystallogr. Commun. 2015, E71, o491.

  16. Shoemaker, R. H. Nat. Rev. Cancer 2006, 6, 813.

    Article  CAS  PubMed  Google Scholar 

  17. Gildeeva, G. N. Vestn. Roszdravnadzora 2015, 5, 59.

    Google Scholar 

  18. Mosmann, T. J. Immunol. Methods 1983, 65, 55.

    Article  CAS  Google Scholar 

  19. Wang, D.; Lippard, S. J. Nat. Rev. Drug Discovery 2005, 4, 307.

    Article  CAS  Google Scholar 

  20. Checchi, S.; Papini, P.; Ridi, M. Gazz. Chim. Ital. 1955, 85, 1160.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    Dar’ya L. Alekseeva, Viktoriya Yu. Rakhimova, Artem S. Minin, Anna V. Belousova & Elena V. Sadchikova

  2. Ural State Medical University, 32 Dekabristov St., Yekaterinburg, 620026, Russia

    Artem S. Minin & Elena V. Sadchikova

  3. M. N. Mikheev Institute of Metal Physics, Ural Branch of the Russian Academy of Sciences, 18 Sofii Kovalevskoy St., Yekaterinburg, 620108, Russia

    Artem S. Minin

  4. Institute of Immunology and Physiology, Ural Branch of the Russian Academy of Sciences, 106 Pervomayskaya St., Yekaterinburg, 620049, Russia

    Anna V. Belousova

Authors
  1. Dar’ya L. Alekseeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Viktoriya Yu. Rakhimova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Artem S. Minin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Anna V. Belousova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Elena V. Sadchikova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Elena V. Sadchikova.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(12), 1145–1152

Electronic supplementary material

ESM 1

(PDF 3822 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Alekseeva, D.L., Rakhimova, V.Y., Minin, A.S. et al. Synthesis and properties of 5-aryl-3-diazo-3H-pyrazoles and 3-aryl-1H-pyrazole-5-diazonium salts. Preparation and cytolytic activity studies of 2-arylpyrazolo-[5,1-c][1,2,4]benzotriazines. Chem Heterocycl Comp 54, 1145–1152 (2018). https://doi.org/10.1007/s10593-019-02406-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02406-8

Keywords

Search

Navigation