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Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties

Sapozhnikova, Ksenia A., Slesarchuk, Nikita A., Orlov, Alexey A., Khvatov, Evgeny V., Radchenko, Eugene V., Chistov, Alexey A., Ustinov, Alexey V., Palyulin, Vladimir A., Kozlovskaya, Liubov I., Osolodkin, Dmitry I., Korshun, Vladimir A., Brylev, Vladimir A.
RSC advances 2019 v.9 no.45 pp. 26014-26023
Tick-borne encephalitis virus, absorbance, acetic acid, antiviral agents, antiviral properties, cell culture, fluorescence, median effective concentration, solubility, uracil
The propargylamide of N3-Pom-protected 5-(perylen-3-ylethynyl)uracil acetic acid, a universal precursor, was used in a CuAAC click reaction for the synthesis of several derivatives, including three ramified molecules with high activities against tick-borne encephalitis virus (TBEV). Pentaerythritol-based polyazides were used for the assembly of molecules containing 2⋯4 antiviral 5-(perylen-3-ylethynyl)uracil scaffolds, the first examples of polyvalent perylene antivirals. Cluster compounds showed enhanced absorbance, however, their fluorescence was reduced due to self-quenching. Due to the solubility issues, Pom group removal succeeded only for compounds with one peryleneethynyluracil unit. Four compounds, including one ramified cluster 9f, showed remarkable 1⋯3 nM EC₅₀ values against TBEV in cell culture.