Synthesis and antiviral evaluation of 7-O-arylmethylquercetin derivatives against SARS-associated coronavirus (SCV) and hepatitis C virus (HCV)

Arch Pharm Res. 2012 Jan;35(1):77-85. doi: 10.1007/s12272-012-0108-9. Epub 2012 Feb 2.

Abstract

Aryl diketoacid (ADK) is well known for antiviral activity which can be enhanced by introduction of an aromatic arylmethyl substituent. A natural flavonoid quercetin has a 3,5-dihydroxychromone pharmacophore which is in bioisosteric relationship with the 1,3-diketoacid moiety of the ADK. Thus, it was of our interest to test the antiviral activity of the quercetin derivatives with an arylmethyl group attached. In this study, we prepared a series of the 7-O-arylmethylquercetin derivatives with various aromatic substituents and evaluated their antiviral activity against the SARS-associated coronavirus (SARS-CoV, SCV) as well as hepatitis C virus (HCV). Single difference in the aromatic substituent fine-tuned the biological activity of the 7-O-arylmethylquercetin derivatives to result in two different classes of derivatives selectively active against SCV and HCV.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology*
  • Cell Line, Tumor
  • Hepacivirus / drug effects*
  • Hepacivirus / physiology
  • Humans
  • Quercetin / chemical synthesis*
  • Quercetin / pharmacology*
  • SARS Virus / drug effects*
  • SARS Virus / physiology
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Quercetin