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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 10, pp 989–992 | Cite as

Synthesis and X-ray structural studies of 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-а]pyrimidine L-arginine and piperidine salts

  • Pavel А. Slepukhin
  • Egor K. Voinkov
  • Eugeny N. Ulomskiy
  • Konstantin V. Savateev
  • Dmitry S. Kopchuk
  • Grigory V. ZyryanovEmail author
  • Victor V. Fedotov
  • Valery N. Charushin
  • Oleg N. Chupakhin
  • Vladimir L. Rusinov
Article
  • 26 Downloads

The previously described L-argininium 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidinide monohydrate and piperidinium 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidinide, which has not been described previously, were synthesized as promising antiviral drugs. A detailed comparison of the crystal structures of these two compounds was performed. It is shown that the replacement of the L-arginine cation with piperidinium one leads to a serious reorganization of the system of intermolecular hydrogen bonds in the solid state, which, in our opinion, can have a significant impact on the interaction of the new drug with biological targets. Thus, by comparing the X-ray structural analysis data, the probability of the influence of the nature of the counterion on the biological effect of the drug was demonstrated.

Keywords

L-argininium salt piperidinium salt 1,2,4-triazolo[1,5-а]pyrimidines antiviral activity comparison of structures by X-ray structural analysis 

Notes

This work was supported by the Ministry of Education and Science of the Russian Federation (grant 4.6351.2017 / 8.9).

Supplementary material

10593_2019_2567_MOESM1_ESM.pdf (361 kb)
ESM 1 (PDF 360 kb)

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Copyright information

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

Authors and Affiliations

  • Pavel А. Slepukhin
    • 1
    • 2
  • Egor K. Voinkov
    • 1
  • Eugeny N. Ulomskiy
    • 1
    • 2
  • Konstantin V. Savateev
    • 1
    • 2
  • Dmitry S. Kopchuk
    • 1
    • 2
  • Grigory V. Zyryanov
    • 1
    • 2
    Email author
  • Victor V. Fedotov
    • 1
  • Valery N. Charushin
    • 1
    • 2
  • Oleg N. Chupakhin
    • 1
    • 2
  • Vladimir L. Rusinov
    • 1
    • 2
  1. 1.Ural Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia
  2. 2.Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesYekaterinburgRussia

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