Hydrazines in the Synthesis of Cytotoxic N-Aryl(alkyl)-N-(hexaoxazadispiroalkyl)amines

Abstract

An efficient method has been developed for the synthesis of N-aryl(alkyl)-N-(hexaoxazadispiroalkanyl)amines by the reaction of 3,6-di(spiroalkanyl)-substituted heptaoxacycloundecanes with hydrazine derivatives (3-chlorophenylhydrazine, phenylhydrazine, 2,4-dinitrophenylhydrazine, and tert-butylhydrazine) with Sm-containing catalysts. It was found that amines with macrocyclic spiro-linked azatriperoxide substituents exhibit a high cytotoxic activity against Jurkat, K562, and U937 tumor cell line and normal fibroblast cell line.

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ACKNOWLEDGMENTS

Cytotoxicity testing was performed at the Laboratory of Biological Screening and Molecular Design at the IPC RAS. The structural study was performed at the “Agidel” Center for Collective Use at the IPC RAS.

Funding

The work was financially supported by the Russian Science Foundation (project no. 18-73-00014).

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Correspondence to N. N. Makhmudiyarova.

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Makhmudiyarova, N.N., Ishmukhametova, I.R., Dzhemileva, L.U. et al. Hydrazines in the Synthesis of Cytotoxic N-Aryl(alkyl)-N-(hexaoxazadispiroalkyl)amines. Russ J Org Chem 56, 797–801 (2020). https://doi.org/10.1134/S1070428020050115

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Keywords:

  • catalysis
  • recycling
  • substituted hydrazines
  • heptaoxadispiroalkanes
  • N-aryl(alkyl)-N-(hexaoxazadispiroalkanyl)amines