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

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Highlights

  • Twenty-five novel chalcone derivatives were designed and synthesized.

  • Compound d2 exhibited excellent antiviral activity against TMV and CMV.

  • Compound d2 showed a strong combining capacity with TMV-CP.

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.

Graphical abstract

Novel chalcone derivatives containing a purine and benzenesulfonamide moiety were synthesized. Compound d2 exhibited excellent antiviral activity against TMV and CMV. The interaction mode of the compound d2 with TMV-CP was performed through molecular docking, fluorescence titration (FT) and microscale thermophoresis (MST) techniques.

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Acknowledgments

This study was supported by the National Natural Science Foundation of China (Nos. 21562013 and 21362004), Subsidy Project for Outstanding Key Laboratory of Guizhou Province in China (No. 20154004), the Provincial University Cooperation Plan of Guizhou Province in China (No. 20147001) and Collaborative Innovation Center for Natural Products and Biological Drugs of Yunnan.

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