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Synthesis and Cytotoxicity of bis(pyrazol-1-yl)-Alkane Derivatives with Polymethylene Linkers and Related Mono- and Dipyrazolium Salts. / Zatonskaya, Lina V.; Schepetkin, Igor A.; Petrenko, Tatiana V. et al.

In: Chemistry of Heterocyclic Compounds, Vol. 52, No. 6, 01.06.2016, p. 388-401.

Research output: Contribution to journal › Article › peer-review

Harvard

Zatonskaya, LV, Schepetkin, IA, Petrenko, TV, Ogorodnikov, VD, Khlebnikov, AI & Potapov, AS 2016, 'Synthesis and Cytotoxicity of bis(pyrazol-1-yl)-Alkane Derivatives with Polymethylene Linkers and Related Mono- and Dipyrazolium Salts', Chemistry of Heterocyclic Compounds, vol. 52, no. 6, pp. 388-401. https://doi.org/10.1007/s10593-016-1900-0

APA

Zatonskaya, L. V., Schepetkin, I. A., Petrenko, T. V., Ogorodnikov, V. D., Khlebnikov, A. I., & Potapov, A. S. (2016). Synthesis and Cytotoxicity of bis(pyrazol-1-yl)-Alkane Derivatives with Polymethylene Linkers and Related Mono- and Dipyrazolium Salts. Chemistry of Heterocyclic Compounds, 52(6), 388-401. https://doi.org/10.1007/s10593-016-1900-0

Vancouver

Zatonskaya LV, Schepetkin IA, Petrenko TV, Ogorodnikov VD, Khlebnikov AI, Potapov AS. Synthesis and Cytotoxicity of bis(pyrazol-1-yl)-Alkane Derivatives with Polymethylene Linkers and Related Mono- and Dipyrazolium Salts. Chemistry of Heterocyclic Compounds. 2016 Jun 1;52(6):388-401. doi: 10.1007/s10593-016-1900-0

Author

Zatonskaya, Lina V. ; Schepetkin, Igor A. ; Petrenko, Tatiana V. et al. / Synthesis and Cytotoxicity of bis(pyrazol-1-yl)-Alkane Derivatives with Polymethylene Linkers and Related Mono- and Dipyrazolium Salts. In: Chemistry of Heterocyclic Compounds. 2016 ; Vol. 52, No. 6. pp. 388-401.

BibTeX

@article{c4e110343cb44b7a91ba235cfd419766,
title = "Synthesis and Cytotoxicity of bis(pyrazol-1-yl)-Alkane Derivatives with Polymethylene Linkers and Related Mono- and Dipyrazolium Salts",
abstract = "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.",
keywords = "alkylation, bis(pyrazol-1-yl)alkanes, cytotoxicity, dipyrazolium salts, iodination, iodo derivatives, superbasic medium",
author = "Zatonskaya, {Lina V.} and Schepetkin, {Igor A.} and Petrenko, {Tatiana V.} and Ogorodnikov, {Vladimir D.} and Khlebnikov, {Andrei I.} and Potapov, {Andrei S.}",
year = "2016",
month = jun,
day = "1",
doi = "10.1007/s10593-016-1900-0",
language = "English",
volume = "52",
pages = "388--401",
journal = "Chemistry of Heterocyclic Compounds",
issn = "0009-3122",
publisher = "Springer New York",
number = "6",

}

RIS

TY - JOUR

T1 - Synthesis and Cytotoxicity of bis(pyrazol-1-yl)-Alkane Derivatives with Polymethylene Linkers and Related Mono- and Dipyrazolium Salts

AU - Zatonskaya, Lina V.

AU - Schepetkin, Igor A.

AU - Petrenko, Tatiana V.

AU - Ogorodnikov, Vladimir D.

AU - Khlebnikov, Andrei I.

AU - Potapov, Andrei S.

PY - 2016/6/1

Y1 - 2016/6/1

N2 - 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.

AB - 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.

KW - alkylation

KW - bis(pyrazol-1-yl)alkanes

KW - cytotoxicity

KW - dipyrazolium salts

KW - iodination

KW - iodo derivatives

KW - superbasic medium

UR - http://www.scopus.com/inward/record.url?scp=85028274655&partnerID=8YFLogxK

U2 - 10.1007/s10593-016-1900-0

DO - 10.1007/s10593-016-1900-0

M3 - Article

AN - SCOPUS:85028274655

VL - 52

SP - 388

EP - 401

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 6

ER -

ID: 25398054