Synthesis and structure-activity relationships of imidazole-coumarin conjugates against hepatitis C virus

Shwu Chen Tsay; Shu Yu Lin; Wen Chieh Huang; Ming Hua Hsu; Kuo Chu Hwang; Chun Cheng Lin; Jia Cherng Horng; I. Chia Chen; Jih Ru Hwu; Fa Kuen Shieh; Pieter Leyssen; Johan Neyts

doi:10.3390/molecules21020228

Synthesis and structure-activity relationships of imidazole-coumarin conjugates against hepatitis C virus

Shwu Chen Tsay, Shu Yu Lin, Wen Chieh Huang, Ming Hua Hsu, Kuo Chu Hwang, Chun Cheng Lin, Jia Cherng Horng, I. Chia Chen, Jih Ru Hwu, Fa Kuen Shieh, Pieter Leyssen, Johan Neyts

Department of Chemistry

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

30 Scopus citations

Abstract

A series of new conjugated compounds with a-SCH₂-linkage were synthesized by chemical methods from imidazole and coumarin derivatives. The experimental results indicate that of the twenty newly synthesized imidazole-coumarin conjugates, three of them exhibited appealing EC₅₀ values (5.1-8.4 μM) and selective indices >20 against hepatitis C virus. Their potency and selectivity were increased substantially by modification of their structure with two factors: imidazole nucleus with a hydrogen atom at the N(1) position and coumarin nucleus with a substituent, such as Cl, F, Br, Me, and OMe. These guidelines provide valuable information for further development of conjugated compounds as anti-viral agents.

Original language	English
Article number	228
Journal	Molecules
Volume	21
Issue number	2
DOIs	https://doi.org/10.3390/molecules21020228
State	Published - Feb 2016

Keywords

Coumarin
Hepatitis C virus
Imidazole
Nitrogen heterocycles
Structure-activity relationships

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title = "Synthesis and structure-activity relationships of imidazole-coumarin conjugates against hepatitis C virus",

abstract = "A series of new conjugated compounds with a-SCH2-linkage were synthesized by chemical methods from imidazole and coumarin derivatives. The experimental results indicate that of the twenty newly synthesized imidazole-coumarin conjugates, three of them exhibited appealing EC50 values (5.1-8.4 μM) and selective indices >20 against hepatitis C virus. Their potency and selectivity were increased substantially by modification of their structure with two factors: imidazole nucleus with a hydrogen atom at the N(1) position and coumarin nucleus with a substituent, such as Cl, F, Br, Me, and OMe. These guidelines provide valuable information for further development of conjugated compounds as anti-viral agents.",

keywords = "Coumarin, Hepatitis C virus, Imidazole, Nitrogen heterocycles, Structure-activity relationships",

author = "Tsay, {Shwu Chen} and Lin, {Shu Yu} and Huang, {Wen Chieh} and Hsu, {Ming Hua} and Hwang, {Kuo Chu} and Lin, {Chun Cheng} and Horng, {Jia Cherng} and Chen, {I. Chia} and Hwu, {Jih Ru} and Shieh, {Fa Kuen} and Pieter Leyssen and Johan Neyts",

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T1 - Synthesis and structure-activity relationships of imidazole-coumarin conjugates against hepatitis C virus

AU - Tsay, Shwu Chen

AU - Lin, Shu Yu

AU - Huang, Wen Chieh

AU - Hsu, Ming Hua

AU - Hwang, Kuo Chu

AU - Lin, Chun Cheng

AU - Horng, Jia Cherng

AU - Chen, I. Chia

AU - Hwu, Jih Ru

AU - Shieh, Fa Kuen

AU - Leyssen, Pieter

AU - Neyts, Johan

PY - 2016/2

Y1 - 2016/2

N2 - A series of new conjugated compounds with a-SCH2-linkage were synthesized by chemical methods from imidazole and coumarin derivatives. The experimental results indicate that of the twenty newly synthesized imidazole-coumarin conjugates, three of them exhibited appealing EC50 values (5.1-8.4 μM) and selective indices >20 against hepatitis C virus. Their potency and selectivity were increased substantially by modification of their structure with two factors: imidazole nucleus with a hydrogen atom at the N(1) position and coumarin nucleus with a substituent, such as Cl, F, Br, Me, and OMe. These guidelines provide valuable information for further development of conjugated compounds as anti-viral agents.

AB - A series of new conjugated compounds with a-SCH2-linkage were synthesized by chemical methods from imidazole and coumarin derivatives. The experimental results indicate that of the twenty newly synthesized imidazole-coumarin conjugates, three of them exhibited appealing EC50 values (5.1-8.4 μM) and selective indices >20 against hepatitis C virus. Their potency and selectivity were increased substantially by modification of their structure with two factors: imidazole nucleus with a hydrogen atom at the N(1) position and coumarin nucleus with a substituent, such as Cl, F, Br, Me, and OMe. These guidelines provide valuable information for further development of conjugated compounds as anti-viral agents.

KW - Coumarin

KW - Hepatitis C virus

KW - Imidazole

KW - Nitrogen heterocycles

KW - Structure-activity relationships

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Synthesis and structure-activity relationships of imidazole-coumarin conjugates against hepatitis C virus

Abstract

Keywords

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