Synthesis and Cytotoxicity of bis(pyrazol-1-yl)-Alkane Derivatives with Polymethylene Linkers and Related Mono- and Dipyrazolium Salts

Lina V. Zatonskaya, Igor A. Schepetkin, Tatiana V. Petrenko, Vladimir D. Ogorodnikov, Andrei I. Khlebnikov, Andrei S. Potapov

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

[Figure not available: see fulltext.] Reactions of α,ω-dibromoalkanes with pyrazole and 3,5-dimethylpyrazole in superbasic medium of dimethyl sulfoxide – potassium hydroxide were used for the synthesis of bidentate ligands: bis(pyrazol-1-yl)alkanes and bis(3,5-dimethylpyrazol-1-yl)alkanes linked by alkyl chains containing between four and twelve methylene groups. Oxidative iodination of the obtained compounds with I2–HIO3–H2SO4 system in acetic acid provided diiodo derivatives: bis(4-iodopyrazol-1-yl)alkanes and bis(4-iodo-3,5-dimethylpyrazol-1-yl)alkanes. The obtained diiodo derivatives of pyrazole were further converted to mono- and dipyrazolium salts by alkylation of nitrogen atom at position 2 of the pyrazole rings with iodomethane, as well as with methyl triflate. These products are of interest as precursors to mesoionic N-heterocyclic carbene complexes. The cytotoxicity of the obtained compounds was studied against THP-1 monocytic leukemia cells.

Original languageEnglish
Pages (from-to)388-401
Number of pages14
JournalChemistry of Heterocyclic Compounds
Volume52
Issue number6
DOIs
Publication statusPublished - 1 Jun 2016

    Fingerprint

Keywords

  • alkylation
  • bis(pyrazol-1-yl)alkanes
  • cytotoxicity
  • dipyrazolium salts
  • iodination
  • iodo derivatives
  • superbasic medium

ASJC Scopus subject areas

  • Organic Chemistry

Cite this