Contrasting reactivity of fluorinated 2,6-heptanediones towards amines and ammonia, leading to cyclohexanediones or 2-oxa-6-azabicyclo[2.2.2]octanes and evaluation of their cytotoxicity

Nadiia V. Pikun, Natalya P. Kolesnyk, Eduard B. Rusanov, Aiva Plotniece, Arkadij Sobolev, Ilona Domracheva, Yuriy G. Shermolovich

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The reactivity and synthetic utility of dialkyl 2,4-diacetyl-2,4-difluoro-3-phenylpentanedioates 1 (2,6-heptanediones) as new fluorinated reagents prepared from the reaction of 1,4-dihydropyridines with Selectfluor® for the synthesis of carbocycles and heterocyclic bridged systems is described. The contrasting behaviour of fluorinated 2,6-heptanediones 1 towards the reaction with amines or ammonia has been revealed. 2,6-Heptanediones 1 with alkylamines form alkylammonium 3-acetyl-5-(alkyloxycarbonyl)-3,5-difluoro-2,6-dioxo-4-phenylcyclohexan-1-ides 2; however, with the less basic aniline, they do not react under similar conditions. 2,6-Heptanediones with aqueous ammonia give alkyl 4,7-difluoro-3-hydroxy-1,3-dimethyl-5-oxo-8-phenyl-2-oxa-6-azabicyclo[2.2.2]octane-7-carboxylates 4. The cytotoxicity of 2,6-heptanediones 1a,c, the salts of 3-acetyl-5-(alkoxycarbonyl)-3,5-difluoro-2,6-dioxo-4-phenylcyclohexan-1-ides 2a,c-f, and 2-oxa-6-azabicyclo[2.2.2]octanes 4a-c on different cancer cell lines and "normal" cells has been evaluated, thus providing a basis for further studies concerning the potential use of these new compounds.

Original languageEnglish
Pages (from-to)10537-10544
JournalNew Journal of Chemistry
Volume43
Issue number26
DOIs
Publication statusPublished - 2019
Externally publishedYes

Field of Science

  • 3.1 Basic medicine
  • 1.4 Chemical sciences

Publication Type

  • 1.1. Scientific article indexed in Web of Science and/or Scopus database

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