Design, synthesis, and bioevaluation of paeonol derivatives as potential anti-HBV agents

Tsurng Juhn Huang, Hong Chuang, Yu Chuan Liang, Hui Hsien Lin, Jia Cherng Horng, Yu Cheng Kuo, Chia Wen Chen, Fu Yuan Tsai, Shih Chieh Yen, Shih Ching Chou, Ming Hua Hsu

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25 Citations (Scopus)

Abstract

Hepatitis B virus (HBV) is a causative reagent that frequently causes progressive liver diseases, leading to the development of acute, chronic hepatitis, cirrhosis, and eventually hepatocellular carcinoma (HCC). Despite several antiviral drugs including interferon-α and nucleotide derivatives are approved for clinical treatment for HBV, critical issues remain unresolved, e.g., low-to-moderate efficacy, adverse side effects, and resistant strains. In this study, novel Paeonol-phenylsulfonyl derivatives were synthesized and their antiviral effect against HBV was evaluated. The experimental results indicated that these compounds process significant antiviral potential, including the inhibition of viral antigen expression and secretion, and the suppression of HBV viral DNA replication. Among compounds synthesized in this research, compound 2-acetyl-5-methoxyphenyl 4-methoxybenzenesulfonate (7f) had the most potent inhibitory activity with IC50 value of 0.36 μM, and high selectivity index, SI (TC50/IC50) 47.75; which exhibited an apparent inhibition effect on viral gene expression and viral propagation in cell culture model. So, we believe our compounds could serve as reservoir for antiviral drug development.

Original languageEnglish
Pages (from-to)428-435
Number of pages8
JournalEuropean Journal of Medicinal Chemistry
Volume90
DOIs
Publication statusPublished - 2015 Jan 27

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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    Huang, T. J., Chuang, H., Liang, Y. C., Lin, H. H., Horng, J. C., Kuo, Y. C., Chen, C. W., Tsai, F. Y., Yen, S. C., Chou, S. C., & Hsu, M. H. (2015). Design, synthesis, and bioevaluation of paeonol derivatives as potential anti-HBV agents. European Journal of Medicinal Chemistry, 90, 428-435. https://doi.org/10.1016/j.ejmech.2014.11.050