Synthesis, antiviral activity, and molecular docking study of trans-ferulic acid derivatives containing acylhydrazone moiety

Bioorg Med Chem Lett. 2017 Sep 1;27(17):4096-4100. doi: 10.1016/j.bmcl.2017.07.038. Epub 2017 Jul 15.

Abstract

In this study, we report the synthesis and antiviral activity of trans-ferulic acid derivatives containing acylhydrazone moiety. Biological tests demonstrated that most target compounds showed potent antiviral activity against tobacco mosaic virus (TMV). Compound D4 showed remarkable inactivating activity with EC50 value of 36.59μg/mL, which was obviously superior to ribavirin (126.05μg/mL). Molecular docking results revealed that compound D4 exhibited the optimal combining capacity with five hydrogen bonds to different amino-acid residues of TMV coat protein (TMV-CP). Docking results were consistent with the inactivating activity of target compounds against TMV.

Keywords: Acylhydrazone; Antiviral activity; Ferulic acid derivatives; Molecular docking; TMV-CP.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Coumaric Acids / chemical synthesis
  • Coumaric Acids / chemistry
  • Coumaric Acids / pharmacology*
  • Dose-Response Relationship, Drug
  • Hydrazones / chemistry
  • Hydrazones / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Docking Simulation*
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tobacco Mosaic Virus / drug effects*

Substances

  • Antiviral Agents
  • Coumaric Acids
  • Hydrazones
  • ferulic acid