The synthesis and biological evaluation of A- and B-ring fluorinated flavones and their key intermediates

•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 depe...

Full description

Saved in:
Bibliographic Details
Published in:Journal of fluorine chemistry 2021-09, Vol.249, p.109857, Article 109857
Main Authors: Shcherbakov, Konstantin V., Panova, Mariya A., Burgart, Yanina V., Zarubaev, Vladimir V., Gerasimova, Natalya A., Evstigneeva, Natalya P., Saloutin, Victor I.
Format: Article
Language:English
Subjects:
1,3-Diaryl-1,3-diketones
Anti-influenza and antimycotic activity
Antiinfectives and antibacterials
Baker-Venkataraman rearrangement
Cyclization
Diketones
Flavones
Fluorine
Influenza
Intermediates
Polyfluoroflavones
Prototropic tautomerism
Synthesis
Tautomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:•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. [Display omitted]
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2021.109857