Synthesis of 4'-Substituted Carbocyclic Uracil Derivatives and Their Monophosphate Prodrugs as Potential Antiviral Agents

Viruses. 2023 Feb 16;15(2):544. doi: 10.3390/v15020544.

Abstract

Over the past decades, both 4'-modified nucleoside and carbocyclic nucleoside analogs have been under the spotlight as several compounds from either family showed anti-HIV, HCV, RSV or SARS-CoV-2 activity. Herein, we designed compounds combining these two features and report the synthesis of a series of novel 4'-substituted carbocyclic uracil derivatives along with their corresponding monophosphate prodrugs. These compounds were successfully prepared in 19 to 22 steps from the commercially available (-)-Vince lactam and were evaluated against a panel of RNA viruses including SARS-CoV-2, influenza A/B viruses and norovirus.

Keywords: SARS-CoV-2; antivirals; carbocyclic nucleosides; influenza virus; norovirus; prodrugs; viral polymerase.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, N.I.H., Extramural

MeSH terms

  • Antiviral Agents / pharmacology
  • COVID-19*
  • Hepatitis C Antibodies
  • Humans
  • Influenza A virus*
  • Influenza B virus
  • Nucleosides
  • Prodrugs* / pharmacology
  • SARS-CoV-2
  • Uracil

Substances

  • Antiviral Agents
  • Hepatitis C Antibodies
  • Nucleosides
  • Prodrugs
  • Uracil