Design and synthesis of pyridine-pyrazole-sulfonate derivatives as potential anti-HBV agents

Hong Chuang, Lin Chiang Sherlock Huang, Mohit Kapoor, Yi Jen Liao, Cheng Lin Yang, Chia Ching Chang, Chun Yi Wu, Jih Ru Hwu, Tsurng Juhn Huang, Ming Hua Hsu

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Hepatitis B virus (HBV) is an infectious disease, which can cause acute and chronic infections. Every year, over 7.5 million persons die due to HBV. No effective drug exists for the treatment of HBV. Thus, we designed and synthesized 16 new pyridine-pyrazole-sulfonate compounds containing pyridine-SCH2-pyrazole and pyridine-pyrazole derivatives. Their structures were characterized by 1H-NMR, 13C-NMR, IR, mass spectroscopy, and high performance liquid chromatography. All the compounds were evaluated for their anti-HBV activities and a structure-activity relationship (SAR) in HepG2 2.2.15 cells was established. We found that the pyridine-pyrazole derivatives could inhibit the HBV gene expression and viral DNA replication. Among these compounds, 2-[3-(2-nitrophenylsulfonyl)oxy-5-pyrazol-yl]pyridine 19d has shown the most potent inhibitory activity with an IC50 value of 9.19 μM and high selectivity index, SI (TC50/IC50) of 35.46. Hence, we believe our compounds could serve as a potential lead compounds for anti-HBV drug development.

Original languageEnglish
Pages (from-to)832-836
Number of pages5
JournalMedChemComm
Volume7
Issue number5
DOIs
Publication statusPublished - 2016 Jan 1

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Viruses
Hepatitis B virus
Derivatives
Inhibitory Concentration 50
Nuclear magnetic resonance
Lead compounds
Viral DNA
Hep G2 Cells
High performance liquid chromatography
Structure-Activity Relationship
DNA Replication
Gene expression
Pharmaceutical Preparations
Communicable Diseases
pyridine
pyrazole
Mass Spectrometry
High Pressure Liquid Chromatography
Spectroscopy
Gene Expression

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry

Cite this

Chuang, H., Huang, L. C. S., Kapoor, M., Liao, Y. J., Yang, C. L., Chang, C. C., ... Hsu, M. H. (2016). Design and synthesis of pyridine-pyrazole-sulfonate derivatives as potential anti-HBV agents. MedChemComm, 7(5), 832-836. https://doi.org/10.1039/c6md00008h
Chuang, Hong ; Huang, Lin Chiang Sherlock ; Kapoor, Mohit ; Liao, Yi Jen ; Yang, Cheng Lin ; Chang, Chia Ching ; Wu, Chun Yi ; Hwu, Jih Ru ; Huang, Tsurng Juhn ; Hsu, Ming Hua. / Design and synthesis of pyridine-pyrazole-sulfonate derivatives as potential anti-HBV agents. In: MedChemComm. 2016 ; Vol. 7, No. 5. pp. 832-836.
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Chuang, H, Huang, LCS, Kapoor, M, Liao, YJ, Yang, CL, Chang, CC, Wu, CY, Hwu, JR, Huang, TJ & Hsu, MH 2016, 'Design and synthesis of pyridine-pyrazole-sulfonate derivatives as potential anti-HBV agents', MedChemComm, vol. 7, no. 5, pp. 832-836. https://doi.org/10.1039/c6md00008h

Design and synthesis of pyridine-pyrazole-sulfonate derivatives as potential anti-HBV agents. / Chuang, Hong; Huang, Lin Chiang Sherlock; Kapoor, Mohit; Liao, Yi Jen; Yang, Cheng Lin; Chang, Chia Ching; Wu, Chun Yi; Hwu, Jih Ru; Huang, Tsurng Juhn; Hsu, Ming Hua.

In: MedChemComm, Vol. 7, No. 5, 01.01.2016, p. 832-836.

Research output: Contribution to journalArticle

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AU - Chuang, Hong

AU - Huang, Lin Chiang Sherlock

AU - Kapoor, Mohit

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AU - Yang, Cheng Lin

AU - Chang, Chia Ching

AU - Wu, Chun Yi

AU - Hwu, Jih Ru

AU - Huang, Tsurng Juhn

AU - Hsu, Ming Hua

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AB - Hepatitis B virus (HBV) is an infectious disease, which can cause acute and chronic infections. Every year, over 7.5 million persons die due to HBV. No effective drug exists for the treatment of HBV. Thus, we designed and synthesized 16 new pyridine-pyrazole-sulfonate compounds containing pyridine-SCH2-pyrazole and pyridine-pyrazole derivatives. Their structures were characterized by 1H-NMR, 13C-NMR, IR, mass spectroscopy, and high performance liquid chromatography. All the compounds were evaluated for their anti-HBV activities and a structure-activity relationship (SAR) in HepG2 2.2.15 cells was established. We found that the pyridine-pyrazole derivatives could inhibit the HBV gene expression and viral DNA replication. Among these compounds, 2-[3-(2-nitrophenylsulfonyl)oxy-5-pyrazol-yl]pyridine 19d has shown the most potent inhibitory activity with an IC50 value of 9.19 μM and high selectivity index, SI (TC50/IC50) of 35.46. Hence, we believe our compounds could serve as a potential lead compounds for anti-HBV drug development.

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Chuang H, Huang LCS, Kapoor M, Liao YJ, Yang CL, Chang CC et al. Design and synthesis of pyridine-pyrazole-sulfonate derivatives as potential anti-HBV agents. MedChemComm. 2016 Jan 1;7(5):832-836. https://doi.org/10.1039/c6md00008h