Journal of Fluorine Chemistry, volume 240, pages 109657
7-Imidazolyl-substituted 4'-methoxy and 3',4'-dimethoxy-containing polyfluoroflavones as promising antiviral agents
Konstantin V. Shcherbakov
1
,
Mariya A Artemyeva
1
,
Yanina V. Burgart
1
,
Victor Saloutin
1
,
Alexandrina S Volobueva
2
,
Maria A Misiurina
2
,
Yana L Esaulkova
2
,
Publication type: Journal Article
Publication date: 2020-12-01
Journal:
Journal of Fluorine Chemistry
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor: 1.9
ISSN: 00221139
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Environmental Chemistry
Abstract
A simple and convenient method for the synthesis of new methyl 2-(4-methoxyphenyl)- and 2-(3,4-dimethoxyphenyl)-4-oxo-4H-polyfluorochromen-3-carboxylates as analogs of natural methoxy-containing flavones is proposed. As a result of their directed modification under basic conditions, 7-imidazolyl-substituted derivatives were obtained. In aqueous-organic medium under basic conditions, 5,6,7,8-tetrafluoro-3-(methoxycarbonyl)flavones were transformed into 6,8-difluoro-5-hydroxy-7-(1H-imidazol-1-yl)-3-(methoxycarbonyl)flavones as a result of flavone-5-hydroxyflavone rearrangement, while 6,7,8-trifluorinated analogs underwent a flavone-coumarin rearrangement to give 6,8-difluoro-3-(hydroxyarylidene)-7-(1H-imidazol-1-yl)coumarins under the same conditions. Acid hydrolysis of methyl polyfluoroflavone-3-carboxylates allowed to obtain 2-aryl-4H-polyfluorochromen-4-ones. Evaluation of the antiviral activity of the synthesized compounds against influenza A (H1N1) and Coxsackie B3 viruses showed that 2-(3,4-dimethoxyphenyl)-5,6,8-trifluoro-7-(1H-imidazol-1-yl)-4H-chromene-4-one has the most promising properties.
Top-30
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2 publications, 18.18%
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1 publication, 9.09%
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1 publication, 9.09%
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Citations by publishers
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Elsevier
3 publications, 27.27%
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2 publications, 18.18%
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2 publications, 18.18%
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Wiley
1 publication, 9.09%
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1 publication, 9.09%
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Bentham Science
1 publication, 9.09%
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Thieme
1 publication, 9.09%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Shcherbakov K. V. et al. 7-Imidazolyl-substituted 4'-methoxy and 3',4'-dimethoxy-containing polyfluoroflavones as promising antiviral agents // Journal of Fluorine Chemistry. 2020. Vol. 240. p. 109657.
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Shcherbakov K. V., Artemyeva M. A., Burgart Y. V., Saloutin V., Volobueva A. S., Misiurina M. A., Esaulkova Y. L., Sinegubova E. O., Zarubaev V. 7-Imidazolyl-substituted 4'-methoxy and 3',4'-dimethoxy-containing polyfluoroflavones as promising antiviral agents // Journal of Fluorine Chemistry. 2020. Vol. 240. p. 109657.
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TY - JOUR
DO - 10.1016/j.jfluchem.2020.109657
UR - https://doi.org/10.1016/j.jfluchem.2020.109657
TI - 7-Imidazolyl-substituted 4'-methoxy and 3',4'-dimethoxy-containing polyfluoroflavones as promising antiviral agents
T2 - Journal of Fluorine Chemistry
AU - Shcherbakov, Konstantin V.
AU - Artemyeva, Mariya A
AU - Burgart, Yanina V.
AU - Saloutin, Victor
AU - Volobueva, Alexandrina S
AU - Misiurina, Maria A
AU - Esaulkova, Yana L
AU - Sinegubova, Ekaterina O
AU - Zarubaev, V.V.
PY - 2020
DA - 2020/12/01 00:00:00
PB - Elsevier
SP - 109657
VL - 240
SN - 0022-1139
ER -
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@article{2020_Shcherbakov,
author = {Konstantin V. Shcherbakov and Mariya A Artemyeva and Yanina V. Burgart and Victor Saloutin and Alexandrina S Volobueva and Maria A Misiurina and Yana L Esaulkova and Ekaterina O Sinegubova and V.V. Zarubaev},
title = {7-Imidazolyl-substituted 4'-methoxy and 3',4'-dimethoxy-containing polyfluoroflavones as promising antiviral agents},
journal = {Journal of Fluorine Chemistry},
year = {2020},
volume = {240},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016/j.jfluchem.2020.109657},
pages = {109657},
doi = {10.1016/j.jfluchem.2020.109657}
}