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A straightforward trifluoromethylation at the C6 position of morphinane alkaloids, their modification and evaluation of inhibition of the SARS-CoV-2 main protease. / Finke, Anastasija O.; Krasnov, Vyacheslav I.; Rybalova, Tatyana V. et al.

In: Journal of Fluorine Chemistry, Vol. 271, 110189, 10.2023.

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

Harvard

Finke, AO, Krasnov, VI, Rybalova, TV, Chirkova, VY, Belenkaya, SV, Volosnikova, EA, Shcherbakov, DN & Shults, EE 2023, 'A straightforward trifluoromethylation at the C6 position of morphinane alkaloids, their modification and evaluation of inhibition of the SARS-CoV-2 main protease', Journal of Fluorine Chemistry, vol. 271, 110189. https://doi.org/10.1016/j.jfluchem.2023.110189

APA

Finke, A. O., Krasnov, V. I., Rybalova, T. V., Chirkova, V. Y., Belenkaya, S. V., Volosnikova, E. A., Shcherbakov, D. N., & Shults, E. E. (2023). A straightforward trifluoromethylation at the C6 position of morphinane alkaloids, their modification and evaluation of inhibition of the SARS-CoV-2 main protease. Journal of Fluorine Chemistry, 271, [110189]. https://doi.org/10.1016/j.jfluchem.2023.110189

Vancouver

Finke AO, Krasnov VI, Rybalova TV, Chirkova VY, Belenkaya SV, Volosnikova EA et al. A straightforward trifluoromethylation at the C6 position of morphinane alkaloids, their modification and evaluation of inhibition of the SARS-CoV-2 main protease. Journal of Fluorine Chemistry. 2023 Oct;271:110189. doi: 10.1016/j.jfluchem.2023.110189

Author

Finke, Anastasija O. ; Krasnov, Vyacheslav I. ; Rybalova, Tatyana V. et al. / A straightforward trifluoromethylation at the C6 position of morphinane alkaloids, their modification and evaluation of inhibition of the SARS-CoV-2 main protease. In: Journal of Fluorine Chemistry. 2023 ; Vol. 271.

BibTeX

@article{77daab39b8904e7a92adb9e27637d588,
title = "A straightforward trifluoromethylation at the C6 position of morphinane alkaloids, their modification and evaluation of inhibition of the SARS-CoV-2 main protease",
abstract = "A catalytic trifluoromethylation of stereoisomeric 6-ketomorphinans using Ruppert–Prakash reagent and tetrabutylammonium fluoride (TBAF) was studied. 14β-Hydroxycodeinone, 4-O-methylsinomenine and 1-iodo-4-O-methylsinomenine provided good to excellent yields of the corresponding 6-trifluoromethylated compounds. The new morphinan derivative (6-deoxo-1-iodo-6α-(trifluoromethyl)-4-O-methylsinomenin-6β-ol) was involved in some catalytic transformations for introduction of additional substituent on C-1 position of the morphinan core. The palladium-catalyzed carbonylation–cross coupling reaction of 1-iodo-derivative with phenylacetylene in the presence of PdCl2-(1-Ad)2PBn catalytic system and Mo(CO)6 as a source of carbon monoxide in MeCN proceeds with high selectivity with the formation of alkynyl ketone as the main product. The cyclocondensation with acetamidine hydrochloride afforded the arylpyrimidine – 6α-(trifluoromethyl)-4-O-methylsinomenin-6β-ol hybrid compound. The action of the dehydration system (SOCl2-Py-DMAP) on 6-deoxo-6α-(trifluoromethyl)-4-O-methylsinomenin-6β-ol have led to the formation оf 8β‑chloro-6,7-didehydro-6-(trifluoromethyl)morphinan which showed inhibition the main viral protease (3CLpro) of SARS-CoV-2 at IC50 value of 25 μM.",
keywords = "Carbonylation-cross-coupling reaction, Hydroxycodeinone, Main viral protease 3CLpro, Ruppert–Prakash reagent, SARS-CoV-2, Sinomenine, Trifluoromethylation",
author = "Finke, {Anastasija O.} and Krasnov, {Vyacheslav I.} and Rybalova, {Tatyana V.} and Chirkova, {Varvara Yu} and Belenkaya, {Svetlana V.} and Volosnikova, {Ekaterina A.} and Shcherbakov, {Dmitry N.} and Shults, {Elvira E.}",
note = "We gratefully acknowledge financial support from the Russian Science Foundation (grant No. 23-73-00077 ). We thank the Multi-Access Chemical Research Center SB RAS for spectral and analytical measurements.",
year = "2023",
month = oct,
doi = "10.1016/j.jfluchem.2023.110189",
language = "English",
volume = "271",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - A straightforward trifluoromethylation at the C6 position of morphinane alkaloids, their modification and evaluation of inhibition of the SARS-CoV-2 main protease

AU - Finke, Anastasija O.

AU - Krasnov, Vyacheslav I.

AU - Rybalova, Tatyana V.

AU - Chirkova, Varvara Yu

AU - Belenkaya, Svetlana V.

AU - Volosnikova, Ekaterina A.

AU - Shcherbakov, Dmitry N.

AU - Shults, Elvira E.

N1 - We gratefully acknowledge financial support from the Russian Science Foundation (grant No. 23-73-00077 ). We thank the Multi-Access Chemical Research Center SB RAS for spectral and analytical measurements.

PY - 2023/10

Y1 - 2023/10

N2 - A catalytic trifluoromethylation of stereoisomeric 6-ketomorphinans using Ruppert–Prakash reagent and tetrabutylammonium fluoride (TBAF) was studied. 14β-Hydroxycodeinone, 4-O-methylsinomenine and 1-iodo-4-O-methylsinomenine provided good to excellent yields of the corresponding 6-trifluoromethylated compounds. The new morphinan derivative (6-deoxo-1-iodo-6α-(trifluoromethyl)-4-O-methylsinomenin-6β-ol) was involved in some catalytic transformations for introduction of additional substituent on C-1 position of the morphinan core. The palladium-catalyzed carbonylation–cross coupling reaction of 1-iodo-derivative with phenylacetylene in the presence of PdCl2-(1-Ad)2PBn catalytic system and Mo(CO)6 as a source of carbon monoxide in MeCN proceeds with high selectivity with the formation of alkynyl ketone as the main product. The cyclocondensation with acetamidine hydrochloride afforded the arylpyrimidine – 6α-(trifluoromethyl)-4-O-methylsinomenin-6β-ol hybrid compound. The action of the dehydration system (SOCl2-Py-DMAP) on 6-deoxo-6α-(trifluoromethyl)-4-O-methylsinomenin-6β-ol have led to the formation оf 8β‑chloro-6,7-didehydro-6-(trifluoromethyl)morphinan which showed inhibition the main viral protease (3CLpro) of SARS-CoV-2 at IC50 value of 25 μM.

AB - A catalytic trifluoromethylation of stereoisomeric 6-ketomorphinans using Ruppert–Prakash reagent and tetrabutylammonium fluoride (TBAF) was studied. 14β-Hydroxycodeinone, 4-O-methylsinomenine and 1-iodo-4-O-methylsinomenine provided good to excellent yields of the corresponding 6-trifluoromethylated compounds. The new morphinan derivative (6-deoxo-1-iodo-6α-(trifluoromethyl)-4-O-methylsinomenin-6β-ol) was involved in some catalytic transformations for introduction of additional substituent on C-1 position of the morphinan core. The palladium-catalyzed carbonylation–cross coupling reaction of 1-iodo-derivative with phenylacetylene in the presence of PdCl2-(1-Ad)2PBn catalytic system and Mo(CO)6 as a source of carbon monoxide in MeCN proceeds with high selectivity with the formation of alkynyl ketone as the main product. The cyclocondensation with acetamidine hydrochloride afforded the arylpyrimidine – 6α-(trifluoromethyl)-4-O-methylsinomenin-6β-ol hybrid compound. The action of the dehydration system (SOCl2-Py-DMAP) on 6-deoxo-6α-(trifluoromethyl)-4-O-methylsinomenin-6β-ol have led to the formation оf 8β‑chloro-6,7-didehydro-6-(trifluoromethyl)morphinan which showed inhibition the main viral protease (3CLpro) of SARS-CoV-2 at IC50 value of 25 μM.

KW - Carbonylation-cross-coupling reaction

KW - Hydroxycodeinone

KW - Main viral protease 3CLpro

KW - Ruppert–Prakash reagent

KW - SARS-CoV-2

KW - Sinomenine

KW - Trifluoromethylation

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85171743860&origin=inward&txGid=1017b9fd72f7a55f3c30c5b93c3532ca

UR - https://www.mendeley.com/catalogue/d6be1e7a-7be3-3f15-ab88-5fa01e6d2b4e/

U2 - 10.1016/j.jfluchem.2023.110189

DO - 10.1016/j.jfluchem.2023.110189

M3 - Article

VL - 271

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

M1 - 110189

ER -

ID: 55558587