Chemistry of Heterocyclic Compounds

, Volume 55, Issue 9, pp 856–860 | Cite as

Stable Isotope-Labeled Azoloazines. Synthesis of a 13С and 15N Isotope-Enriched Derivative of Pyrazolo[5,1-c][1,2,4]Triazine –Potential Antidiabetic Agent

  • Tatyana S. Shestakova
  • Oleg S. Eltsov
  • Yuliya А. Yakovleva
  • Sergey L. DeevEmail author
  • Vadim А. Shevyrin
  • Vladimir L. Rusinov
  • Valery N. Charushin
  • Oleg N. Chupakhin

A simple and selective method for introducing stable 13C and 15N isotopes into the structure of the sodium salt of 4-oxo-1,4-dihydropyrazolo[5,1-c][1,2,4]triazine-3,8-dicarboxylic acid diethyl ester, a potential antiglycation agent, has been developed. Labeled [1,3-13C2]-malonic ester (99% 13C) was used as the 13C isotope donor. The introduction of the 15N atom was carried out using enriched sodium nitrite (98% 15N). The obtained 13C2 and 15N isotope-labeled analog of a promising antidiabetic compound of the pyrazolo- [5,1-c][1,2,4]triazine series was characterized by NMR spectroscopy and high-resolution mass spectrometry.


azoloazines pyrazolo[5,1-c][1,2,4]triazines 13С and 15N isotopic labels CID mass spectrum compounds with antidiabetic activity MS/MS experiments NMR spectra spin-spin coupling constants (SSCC) stable isotopes 


This work was carried out as part of the state assignment of the Ministry of Higher Education and Science of the Russian Federation (4.6351.2017/8.9) and with the financial support of the Russian Foundation for Basic Research (grant 17-03-01029)

Supplementary material

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Copyright information

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

Authors and Affiliations

  • Tatyana S. Shestakova
    • 1
  • Oleg S. Eltsov
    • 1
  • Yuliya А. Yakovleva
    • 1
  • Sergey L. Deev
    • 1
    Email author
  • Vadim А. Shevyrin
    • 1
  • Vladimir L. Rusinov
    • 1
    • 2
  • Valery N. Charushin
    • 1
    • 2
  • Oleg N. Chupakhin
    • 1
    • 2
  1. 1.Ural Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia
  2. 2.Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of SciencesYekaterinburgRussia

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