• A
  • A
  • A
  • ABC
  • ABC
  • ABC
  • А
  • А
  • А
  • А
  • А
Regular version of the site

Article

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

RSC advances. 2019. Vol. 9. No. 45. P. 26014-26023.
Vladimir A. Korshun.

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.