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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 12, pp 1145–1152 | Cite as

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

  • Dar’ya L. Alekseeva
  • Viktoriya Yu. Rakhimova
  • Artem S. Minin
  • Anna V. Belousova
  • Elena V. SadchikovaEmail author
Article
  • 11 Downloads

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.

Keywords

2-arylpyrazolo[5,1-c][1,2,4]benzotriazines 3-diazopyrazoles pyrazole-5-diazonium salts antitumor activity azo coupling diazotation heterocyclization 

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Dar’ya L. Alekseeva
    • 1
  • Viktoriya Yu. Rakhimova
    • 1
  • Artem S. Minin
    • 1
    • 2
    • 3
  • Anna V. Belousova
    • 1
    • 4
  • Elena V. Sadchikova
    • 1
    • 2
    Email author
  1. 1.Ural Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia
  2. 2.Ural State Medical UniversityYekaterinburgRussia
  3. 3.M. N. Mikheev Institute of Metal PhysicsUral Branch of the Russian Academy of SciencesYekaterinburgRussia
  4. 4.Institute of Immunology and PhysiologyUral Branch of the Russian Academy of SciencesYekaterinburgRussia

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