PREPARATIVE SYNTHESIS OF POLYSUBSTITUTED 4-(5-ARYLISOXAZOL-3-YL)-1,4-DIHYDROPYRIDINES AND -PYRIDINES

Authors

  • Сергей К. Петкевич Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganova St., Minsk 220072, Belarus
  • Татьяна Д. Зверева Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganova St., Minsk 220072, Belarus
  • Полина С. Шабуня Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 5/2 Akademika V. F. Kuprevicha St., Minsk 220141, Belarus
  • Хонгвей Чжоу College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, China
  • Евгения В. Никитина RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Анастасия А. Ершова RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Владимир П. Зайцев RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Виктор Н. Хрусталев RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Анна А. Романычева Yaroslavl State Pedagogical University named after K. D. Ushinsky 108/1 Respublikanskaya St., Yaroslavl 150000, Russia
  • Антон А. Шетнев Yaroslavl State Pedagogical University named after K. D. Ushinsky 108/1 Respublikanskaya St., Yaroslavl 150000, Russia
  • Владимир И. Поткин Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganova St., Minsk 220072, Belarus

DOI:

https://doi.org/10.1007/6674

Keywords:

aldehydes, 1, 4-dihydropyridines, isoxazoles, pyridines, Hantzsch reaction.

Abstract

Multicomponent condensation of 5-phenyl(p-tolyl)isoxazole-3-carbaldehydes, cyclohexane-1,3-dione (or dimedone), ethyl acetoacetate (or acetylacetone), and ammonium acetate was used to synthesize polysubstituted derivatives of 1,4-dihydropyridines with an isoxazole fragment. As a result of oxidation of the obtained compounds with sodium nitrite, the corresponding substituted pyridine derivatives were formed. Biological testing revealed that some of the obtained compounds exhibited cytotoxic activity against LS174T colorectal cancer cells, as well as antibacterial activity against susceptible strains of Escherichia coli (C600) and Staphylococcus aureus
(ATCC-25923).

 

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Published

2022-07-21

Issue

Vol. 58 No. 6/7 (2022)

Section

Original Papers