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

Research output: Contribution to journalArticle

7 Citations (Scopus)

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 languageEnglish
Article number228
JournalMolecules
Volume21
Issue number2
DOIs
Publication statusPublished - 2016 Feb

Fingerprint

hepatitis
viruses
Structure-Activity Relationship
imidazoles
Viruses
Hepacivirus
Antiviral agents
synthesis
Coumarins
nuclei
linkages
Hydrogen
hydrogen atoms
selectivity
Guidelines
Atoms
coumarin
imidazole

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Tsay, Shwu Chen ; Lin, Shu Yu ; Huang, Wen Chieh ; Hsu, Ming Hua ; Hwang, Kuo Chu ; Lin, Chun Cheng ; Horng, Jia Cherng ; Chen, I. Chia ; Hwu, Jih Ru ; Shieh, Fa Kuen ; Leyssen, Pieter ; Neyts, Johan. / Synthesis and structure-activity relationships of imidazole-coumarin conjugates against hepatitis C virus. In: Molecules. 2016 ; Vol. 21, No. 2.
@article{897ca427d34844a9a475384f2cef21cb,
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.",
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",
year = "2016",
month = "2",
doi = "10.3390/molecules21020228",
language = "English",
volume = "21",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "2",

}

Tsay, SC, Lin, SY, Huang, WC, Hsu, MH, Hwang, KC, Lin, CC, Horng, JC, Chen, IC, Hwu, JR, Shieh, FK, Leyssen, P & Neyts, J 2016, 'Synthesis and structure-activity relationships of imidazole-coumarin conjugates against hepatitis C virus', Molecules, vol. 21, no. 2, 228. https://doi.org/10.3390/molecules21020228

Synthesis and structure-activity relationships of imidazole-coumarin conjugates against hepatitis C virus. / Tsay, Shwu Chen; Lin, Shu Yu; Huang, Wen Chieh; Hsu, Ming Hua; Hwang, Kuo Chu; Lin, Chun Cheng; Horng, Jia Cherng; Chen, I. Chia; Hwu, Jih Ru; Shieh, Fa Kuen; Leyssen, Pieter; Neyts, Johan.

In: Molecules, Vol. 21, No. 2, 228, 02.2016.

Research output: Contribution to journalArticle

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=84962859556&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84962859556&partnerID=8YFLogxK

U2 - 10.3390/molecules21020228

DO - 10.3390/molecules21020228

M3 - Article

C2 - 26901180

AN - SCOPUS:84962859556

VL - 21

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 2

M1 - 228

ER -