Journal of Fluorine Chemistry, volume 249, pages 109857
The synthesis and biological evaluation of A- and B-ring fluorinated flavones and their key intermediates
Konstantin V. Shcherbakov
1
,
Mariya A Panova
1
,
Yanina V. Burgart
1
,
V.V. Zarubaev
2
,
Natalya A Gerasimova
3
,
Natalya P Evstigneeva
3
,
Victor Saloutin
1
3
Ural Research Institute of Dermatovenereology and Immunopathology, 8 Shcherbakova st., Yekaterinburg 620076, Russian Federation
|
Publication type: Journal Article
Publication date: 2021-09-01
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
• Synthesis of new polyfluoroflavones by the Baker-Venkataraman rearrangement. • Study of prototropic tautomeric transformations of 1,3-diaryl-1,3-diketones depending on the nature of the solvent. • Realization of alternative routes for the cyclization of fluorine-containing 1,3-diaryl-1,3-diketones depending on their structure and reaction conditions. • Evaluation of fungistatic and anti-influenza action of 1,3-diaryl-1,3-diketones and flavones. An efficient three-step method for the synthesis of new polyfluoroflavones has been proposed using substituted benzoyl chlorides and 2-hydroxyacetophenone to form the initial 2-(polyfluoroaroyloxy)acetophenones, which are transformed into 1,3-diaryl-1,3-diketones as a result of the Baker-Venkataraman rearrangement. The ability of these 1,3-diketones to undergo keto-enol and ring-chain tautomerism was found, depending on the nature of the solvent. Under acid- or base-catalyzed conditions the alternative cyclization routes of fluorine-containing 1,3-diaryl-1,3-diketones into A - and B -ring halogenated flavones have been reported. The anti-influenza and fungistatic effects of the synthesized compounds were evaluated, and products with promising antimicrobial properties were found.
Top-30
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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. The synthesis and biological evaluation of A- and B-ring fluorinated flavones and their key intermediates // Journal of Fluorine Chemistry. 2021. Vol. 249. p. 109857.
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Shcherbakov K. V., Panova M. A., Burgart Y. V., Zarubaev V., Gerasimova N. A., Evstigneeva N. P., Saloutin V. The synthesis and biological evaluation of A- and B-ring fluorinated flavones and their key intermediates // Journal of Fluorine Chemistry. 2021. Vol. 249. p. 109857.
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TY - JOUR
DO - 10.1016/j.jfluchem.2021.109857
UR - https://doi.org/10.1016/j.jfluchem.2021.109857
TI - The synthesis and biological evaluation of A- and B-ring fluorinated flavones and their key intermediates
T2 - Journal of Fluorine Chemistry
AU - Shcherbakov, Konstantin V.
AU - Panova, Mariya A
AU - Burgart, Yanina V.
AU - Zarubaev, V.V.
AU - Gerasimova, Natalya A
AU - Evstigneeva, Natalya P
AU - Saloutin, Victor
PY - 2021
DA - 2021/09/01 00:00:00
PB - Elsevier
SP - 109857
VL - 249
SN - 0022-1139
ER -
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@article{2021_Shcherbakov,
author = {Konstantin V. Shcherbakov and Mariya A Panova and Yanina V. Burgart and V.V. Zarubaev and Natalya A Gerasimova and Natalya P Evstigneeva and Victor Saloutin},
title = {The synthesis and biological evaluation of A- and B-ring fluorinated flavones and their key intermediates},
journal = {Journal of Fluorine Chemistry},
year = {2021},
volume = {249},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/j.jfluchem.2021.109857},
pages = {109857},
doi = {10.1016/j.jfluchem.2021.109857}
}