SYNTHESIS AND X-RAY STRUCTURAL STUDIES OF 5-METHYL-6-NITRO-7-OXO-4,7-DIHYDRO-1,2,4-TRIAZOLO[1,5-<i>а</i>]PYRIMIDINE L-ARGININE AND PIPERIDINE SALTS

Authors

  • Павел А. Слепухин Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620990, Russia
  • Егор К. Воинков Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Евгений Н. Уломский Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620990, Russia
  • Константин В. Саватеев Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620990, Russia
  • Дмитрий С. Копчук Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620990, Russia
  • Григорий В. Зырянов Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620990, Russia
  • Виктор В. Федотов Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Валерий Н. Чарушин Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620990, Russia
  • Олег Н. Чупахин Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620990, Russia
  • Владимир Л. Русинов Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620990, Russia

DOI:

https://doi.org/10.1007/5113

Keywords:

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

Abstract

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.

Author Biography

Григорий В. Зырянов, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620990, Russia

cтарший научный сотрудник, Группа координационных соединений

Published

2019-09-27

Issue

Section

Original Papers