RSC advances · 2019
Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties.
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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
Аннотация
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.