SYNTHESIS OF BIOLOGICALLY ACTIVE 6-(TOLYLHYDRAZINYLIDENE)PYRAZOLO[1,5-<i>a</i>]PYRIMIDINONES

Authors

  • Янина В. Бургарт Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620108 Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Наталья А. Елькина Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620108
  • Евгений В. Щегольков Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620108 Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Ольга П. Красных Perm National Research Polytechnic University, 29 Komsomolsky Ave., Perm 614990
  • Вера В. Маслова Perm National Research Polytechnic University, 29 Komsomolsky Ave., Perm 614990
  • Галина А. Триандафилова Perm National Research Polytechnic University, 29 Komsomolsky Ave., Perm 614990
  • Сергей Ю. Солодников Perm National Research Polytechnic University, 29 Komsomolsky Ave., Perm 614990
  • Галина Ф. Махаева Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi Proezd, Chernogolovka 142432
  • Ольга Г. Серебрякова Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi Proezd, Chernogolovka 142432
  • Елена В. Рудакова Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi Proezd, Chernogolovka 142432
  • Виктор И. Салоутин Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620108 Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002

DOI:

https://doi.org/10.1007/5403

Keywords:

pyrazolo[1, 5-a]pyrimidinones, acute toxicity, analgesic activity, anticarboxylesterase activity, antiradical activity, ring-chain isomerism, regioisomers

Abstract

New pyrazolo[1,5-a]pyrimidinones functionalized with the tolylhydrazone fragment were obtained as a result of cyclization of 3-oxo-
2-(tolylhydrazinylidene) esters with 3-aminopyrazoles. In this case, methyl- and trifluoromethyl-containing derivatives regioselectively
form pyrazolo[1,5-a]pyrimidin-7-ones, while cyclization of polyfluoroalkyl-substituted analogs can take place competitively with the formation of dihydropyrazolo[1,5-a]pyrimidin-5-ones, for which ring-chain isomerism is characteristic in solution. It was found that 6-(tolylhydrazinylidene)pyrazolo[1,5-a]pyrimidin-7-ones have a pronounced analgesic activity. The trifluoromethyl-containing analog
selectively inhibits carboxylesterase in micromolar concentration.

Authors: Olga P. Krasnykh, Vera V. Maslova, Galina A. Triandafilova, Sergey Yu. Solodnikov, Galina F. Makhaeva, Olga G. Serebryakova, Elena V. Rudakova, Victor I. Saloutin*

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Published

2020-02-28

Issue

Vol. 56 No. 2 (2020)

Section

Original Papers