A SYNTHESIS OF NOVEL 5-METHYLSULFANYLAZOLO[1,5-<i>a</i>]PYRIMIDIN-7(4<i>H</i>)-ONES AND INVESTIGATION OF THEIR CHEMICAL AND CYTOTOXIC PROPERTIES

Authors

  • Daniil N. Lyapustin Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Dilya F. Fayzullina Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Irina V. Marusich Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Svetlana K. Kotovskaya Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Vsevolod V. Melekhin Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002. Ural State Medical University, 3 Repina St., Yekaterinburg 620028
  • Maria D. Tokhtueva Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Evgeny N. Ulomsky Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Vladimir L. Rusinov Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002

Keywords:

azolo[1,5-a]pyrimidines, Meldrum's acid, heterocyclization, electrophilic substitution, antitumor activity

Abstract

A method for the synthesis of novel 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones by heterocyclization of 3-aminoazoles and
5-[bis(methylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-diones was developed. 5-Methylsulfanyl-7-oxo-4,7-dihydroazolo-
[1,5-a]pyrimidine-6-carboxylic acid was isolated during optimization of the process, which allowed us to establish the sequence of
transformations of this heterocyclization reaction. The reactivity of the resulting 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones in
classical electrophilic substitution reactions was studied. The cytotoxic effect of these compounds toward A549, HepG2, and RD tumor
cell lines as well as normal HEK-293 cells was assessed.

Author Biographies

Daniil N. Lyapustin, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002

Даниил Николаевич Ляпустин

Dilya F. Fayzullina, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002

Диля Фаилевна Файзуллина

Irina V. Marusich, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002

Ирина Владимировна Марусич

Svetlana K. Kotovskaya, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002

Светлана Константиновна Котовская

Vsevolod V. Melekhin, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002. Ural State Medical University, 3 Repina St., Yekaterinburg 620028

Всеволод Викторович Мелехин

Maria D. Tokhtueva, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002

Мария Дмитриевна Тохтуева

Evgeny N. Ulomsky, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002

Евгений Нарциссович Уломский

Vladimir L. Rusinov, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002

Владимир Леонидович Русинов

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Published

2024-03-26

Issue

Vol. 60 No. 1/2 (2024)

Section

Original Papers