7-Imidazolyl-substituted 4'-methoxy and 3',4'-dimethoxy-containing polyfluoroflavones as promising antiviral agents

Abstract

Graphical abstract

Antiviral Activity of Peptide-Based Assemblies

“…39 In addition, fluorinated compounds are known as antiviral agents. This includes 3′-fluoropenciclovir analogues, 40 polyfluoroflavones, 41 perfluoroalkyl derivatives of teicoplanin and vancomycin, 42 6′-fluorinated-aristeromycin analogues, 43 fluorinated TiO 2 , 44 and other fluorinated molecules. 45 These observations can explain our results with both DOPA-Phe-Phe and DOPA-Phe(4F)-Phe(4F).…”

Alternative Functionalization of 2‐(3,4‐Dihalophenyl)‐4H‐chromen‐4‐ones via Metal‐Free Nucleophilic Aromatic Fluorine Substitution and Palladium‐Catalyzed Cross‐Coupling Reactions

“…Previously, we found promising anti‐influenza agents in the series of 7‐imidazolyl‐substituted flavones; [7a] therefore, in this work we evaluated the effect of the obtained imidazolyl‐substituted flavones 7a , b and their aza‐analogs 6a , b against influenza A virus (See SI, Table 1) using ribavirin as a positive control. For comparison, the data [12] on the antiviral activity of the initial unsubstituted flavones 1a , b are presented.…”

“…At the same time, the introduction of an azole fragment into flavones is a promising way for obtaining of bioactive compounds with antiviral, [7a] antidiabetic, [8] anticancer, [9] antifungal and anticonvulsant activities [10] . Among diaryl‐containing flavones, new therapeutic agents for the therapy of type‐II diabetes as protein tyrosine Phosphatase‐1B inhibitors have been found [11] …”

Recent advances in the synthesis of 4H-chromen-4-ones (2012 − 2021)

“…419 When using 3-aryl-3-oxopropanoates as starting materials, after activation of 2-fluoroaroyl chlorides with magnesium methoxide and acidic treatment with diluted hydrochloric acid, the desired methyl 2-aryl-4-oxo-4H-chromen-3carboxylates were obtained in good yields (Scheme 78). 420 One-pot domino Friedel-Crafts acylation/annulation reaction of internal alkynes with 2-methoxyaroyl chlorides in the presence of stoichiometric amount of aluminum bromide in dichloromethane prompted a wide variety of 2,3-disubstituted 4H-chromen-4-ones. 421 chlorides underwent annulation reaction with ynamides promoted by tin tetrachloride in dichloromethane at 30 °C to give 3-substituted 2-amino-4H-chromen-4-ones.…”