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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
Article
  • 38 Downloads

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.

Keywords

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 

Notes

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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