Synthesis, antiviral activity, and molecular docking study of trans-ferulic acid derivatives containing acylhydrazone moiety. Issue 17 (1st September 2017)

• Record Type: Journal Article
• Authors: Wang, Zhenzhen; Xie, Dandan; Gan, Xiuhai; Zeng, Song; Zhang, Awei; Yin, Limin; Song, Baoan; Jin, Linhong; Hu, Deyu
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 17(2017)
• Page Start: 4096
• Page End: 4100
• Publication Date: 2017-09-01
• Subjects: TMV tobacco mosaic virus -- 1H NMR 1H nuclear magnetic resonance -- 13C NMR 13C nuclear magnetic resonance -- IR infrared spectroscopy -- EC50 50% effective concentration -- HRMS high-resolution mass spectrometry -- SAR structure–activity relationship -- TMV-CP tobacco mosaic virus coat protein; Ferulic acid derivatives -- Acylhydrazone -- Antiviral activity -- Molecular docking -- TMV-CP; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2017.07.038
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: 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). CompoundD4 showed remarkable inactivating activity with EC50 value of 36.59 μg/mL, which was obviously superior to ribavirin (126.05 μg/mL). Molecular docking results revealed that compoundD4 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.