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Synthesis of Sterically Shielded Nitroxides Using the Reaction of Nitrones with Alkynylmagnesium Bromides. / Dobrynin, Sergey A.; Gulman, Mark M.; Morozov, Denis A. et al.

In: Molecules (Basel, Switzerland), Vol. 27, No. 21, 7626, 07.11.2022.

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

Harvard

Dobrynin, SA, Gulman, MM, Morozov, DA, Zhurko, IF, Taratayko, AI, Sotnikova, YS, Glazachev, YI, Gatilov, YV & Kirilyuk, IA 2022, 'Synthesis of Sterically Shielded Nitroxides Using the Reaction of Nitrones with Alkynylmagnesium Bromides', Molecules (Basel, Switzerland), vol. 27, no. 21, 7626. https://doi.org/10.3390/molecules27217626

APA

Dobrynin, S. A., Gulman, M. M., Morozov, D. A., Zhurko, I. F., Taratayko, A. I., Sotnikova, Y. S., Glazachev, Y. I., Gatilov, Y. V., & Kirilyuk, I. A. (2022). Synthesis of Sterically Shielded Nitroxides Using the Reaction of Nitrones with Alkynylmagnesium Bromides. Molecules (Basel, Switzerland), 27(21), [7626]. https://doi.org/10.3390/molecules27217626

Vancouver

Dobrynin SA, Gulman MM, Morozov DA, Zhurko IF, Taratayko AI, Sotnikova YS et al. Synthesis of Sterically Shielded Nitroxides Using the Reaction of Nitrones with Alkynylmagnesium Bromides. Molecules (Basel, Switzerland). 2022 Nov 7;27(21):7626. doi: 10.3390/molecules27217626

Author

Dobrynin, Sergey A. ; Gulman, Mark M. ; Morozov, Denis A. et al. / Synthesis of Sterically Shielded Nitroxides Using the Reaction of Nitrones with Alkynylmagnesium Bromides. In: Molecules (Basel, Switzerland). 2022 ; Vol. 27, No. 21.

BibTeX

@article{74bbb45e5bd94fb5a027664dd1ed9d3c,
title = "Synthesis of Sterically Shielded Nitroxides Using the Reaction of Nitrones with Alkynylmagnesium Bromides",
abstract = "Sterically shielded nitroxides, which demonstrate high resistance to bioreduction, are the spin labels of choice for structural studies inside living cells using pulsed EPR and functional MRI and EPRI in vivo. To prepare new sterically shielded nitroxides, a reaction of cyclic nitrones, including various 1-pyrroline-1-oxides, 2,5-dihydroimidazole-3-oxide and 4H-imidazole-3-oxide with alkynylmagnesium bromide wereused. The reaction gave corresponding nitroxides with an alkynyl group adjacent to the N-O moiety. The hydrogenation of resulting 2-ethynyl-substituted nitroxides with subsequent re-oxidation of the N-OH group produced the corresponding sterically shielded tetraalkylnitroxides of pyrrolidine, imidazolidine and 2,5-dihydroimidazole series. EPR studies revealed large additional couplings up to 4 G in the spectra of pyrrolidine and imidazolidine nitroxides with substituents in 3- and/or 4-positions of the ring.",
keywords = "nitrones, nitroxides, organometallic compounds",
author = "Dobrynin, {Sergey A.} and Gulman, {Mark M.} and Morozov, {Denis A.} and Zhurko, {Irina F.} and Taratayko, {Andrey I.} and Sotnikova, {Yulia S.} and Glazachev, {Yurii I.} and Gatilov, {Yuri V.} and Kirilyuk, {Igor A.}",
note = "Publisher Copyright: {\textcopyright} 2022 by the authors.",
year = "2022",
month = nov,
day = "7",
doi = "10.3390/molecules27217626",
language = "English",
volume = "27",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "21",

}

RIS

TY - JOUR

T1 - Synthesis of Sterically Shielded Nitroxides Using the Reaction of Nitrones with Alkynylmagnesium Bromides

AU - Dobrynin, Sergey A.

AU - Gulman, Mark M.

AU - Morozov, Denis A.

AU - Zhurko, Irina F.

AU - Taratayko, Andrey I.

AU - Sotnikova, Yulia S.

AU - Glazachev, Yurii I.

AU - Gatilov, Yuri V.

AU - Kirilyuk, Igor A.

N1 - Publisher Copyright: © 2022 by the authors.

PY - 2022/11/7

Y1 - 2022/11/7

N2 - Sterically shielded nitroxides, which demonstrate high resistance to bioreduction, are the spin labels of choice for structural studies inside living cells using pulsed EPR and functional MRI and EPRI in vivo. To prepare new sterically shielded nitroxides, a reaction of cyclic nitrones, including various 1-pyrroline-1-oxides, 2,5-dihydroimidazole-3-oxide and 4H-imidazole-3-oxide with alkynylmagnesium bromide wereused. The reaction gave corresponding nitroxides with an alkynyl group adjacent to the N-O moiety. The hydrogenation of resulting 2-ethynyl-substituted nitroxides with subsequent re-oxidation of the N-OH group produced the corresponding sterically shielded tetraalkylnitroxides of pyrrolidine, imidazolidine and 2,5-dihydroimidazole series. EPR studies revealed large additional couplings up to 4 G in the spectra of pyrrolidine and imidazolidine nitroxides with substituents in 3- and/or 4-positions of the ring.

AB - Sterically shielded nitroxides, which demonstrate high resistance to bioreduction, are the spin labels of choice for structural studies inside living cells using pulsed EPR and functional MRI and EPRI in vivo. To prepare new sterically shielded nitroxides, a reaction of cyclic nitrones, including various 1-pyrroline-1-oxides, 2,5-dihydroimidazole-3-oxide and 4H-imidazole-3-oxide with alkynylmagnesium bromide wereused. The reaction gave corresponding nitroxides with an alkynyl group adjacent to the N-O moiety. The hydrogenation of resulting 2-ethynyl-substituted nitroxides with subsequent re-oxidation of the N-OH group produced the corresponding sterically shielded tetraalkylnitroxides of pyrrolidine, imidazolidine and 2,5-dihydroimidazole series. EPR studies revealed large additional couplings up to 4 G in the spectra of pyrrolidine and imidazolidine nitroxides with substituents in 3- and/or 4-positions of the ring.

KW - nitrones

KW - nitroxides

KW - organometallic compounds

UR - http://www.scopus.com/inward/record.url?scp=85141595982&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/0bd37df3-c9d3-3963-bb9b-afbda90cb6e4/

U2 - 10.3390/molecules27217626

DO - 10.3390/molecules27217626

M3 - Article

C2 - 36364453

AN - SCOPUS:85141595982

VL - 27

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 21

M1 - 7626

ER -

ID: 39332812