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

doi:10.1039/c6md00008h

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

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 language	English
Pages (from-to)	832-836
Number of pages	5
Journal	MedChemComm
Volume	7
Issue number	5
DOIs	https://doi.org/10.1039/c6md00008h
State	Published - 2016

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@article{39d1f49eda644500846e741060b7e9f2,

title = "Design and synthesis of pyridine-pyrazole-sulfonate derivatives as potential anti-HBV agents",

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.",

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

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

year = "2016",

doi = "10.1039/c6md00008h",

language = "English",

volume = "7",

pages = "832--836",

journal = "MedChemComm",

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TY - JOUR

T1 - Design and synthesis of pyridine-pyrazole-sulfonate derivatives as potential anti-HBV agents

AU - Chuang, Hong

AU - Huang, Lin Chiang Sherlock

AU - Kapoor, Mohit

AU - Liao, Yi Jen

AU - Yang, Cheng Lin

AU - Chang, Chia Ching

AU - Wu, Chun Yi

AU - Hwu, Jih Ru

AU - Huang, Tsurng Juhn

AU - Hsu, Ming Hua

PY - 2016

Y1 - 2016

N2 - 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.

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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DO - 10.1039/c6md00008h

M3 - Article

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SN - 2040-2503

VL - 7

SP - 832

EP - 836

JO - MedChemComm

JF - MedChemComm

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ER -

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

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