Antiviral properties and interaction of novel chalcone derivatives containing a purine and benzenesulfonamide moiety

Bioorg Med Chem Lett. 2018 Jun 15;28(11):2091-2097. doi: 10.1016/j.bmcl.2018.04.042. Epub 2018 Apr 17.

Abstract

A new concise and facile method was explored to synthesize a series of novel chalcone derivatives containing a purine and benzenesulfonamide moiety and their antiviral properties were evaluated against TMV and CMV. Biological assays indicated that several of the derivatives exhibited significant anti-TMV and anti-CMV activities in vivo. In particular, compound d2 displayed excellent inactivating activity against TMV, with the EC50 value of 51.65 μg/mL, which was better than that of ribavirin (150.45 μg/mL). Molecular docking showed that there are four hydrogen bonds between compound d2 and TMV coat protein (TMV-CP). Compound d2 demonstrated strong binding capacity to TMV-CP with Ka = 1.58 × 105 L/mol and Kd = 12.16 μM. These findings indicated that chalcone derivatives are worthy of further research and development as templates for new antiviral agents.

Keywords: Antiviral property; Benzenesulfonamide moiety; Chalcone derivatives; Cucumber mosaic virus; Purine moiety; Tobacco mosaic virus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Benzenesulfonamides
  • Chalcone / chemical synthesis
  • Chalcone / chemistry
  • Chalcone / pharmacology*
  • Cucumovirus / drug effects*
  • Dose-Response Relationship, Drug
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Purines / chemistry
  • Purines / pharmacology*
  • Structure-Activity Relationship
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*
  • Tobacco Mosaic Virus / drug effects*

Substances

  • Antiviral Agents
  • Purines
  • Sulfonamides
  • Chalcone
  • purine