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

Результат исследования: Научные публикации в периодических изданияхстатья

5 Цитирования (Scopus)

Аннотация

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.

Язык оригиналаанглийский
Страницы (с-по)388-401
Число страниц14
ЖурналChemistry of Heterocyclic Compounds
Том52
Номер выпуска6
DOI
СостояниеОпубликовано - 1 июн 2016
Опубликовано для внешнего пользованияДа

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