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10.3390/molecules21020228
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Article

Synthesis and Structure-Activity Relationships of Imidazole-Coumarin Conjugates against Hepatitis C Virus

by
Shwu-Chen Tsay
1,2,*,
Shu-Yu Lin
1,
Wen-Chieh Huang
1,
Ming-Hua Hsu
1,
Kuo Chu Hwang
1,
Chun-Cheng Lin
1,
Jia-Cherng Horng
1,
I-Chia Chen
1,
Jih Ru Hwu
1,2,*,
Fa-Kuen Shieh
2,
Pieter Leyssen
3 and
Johan Neyts
3,*
1
Department of Chemistry & Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 30013, Taiwan
2
Department of Chemistry, National Central University, Jhongli District, Taoyuan City 32001, Taiwan
3
Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven B-3000, Belgium
*
Authors to whom correspondence should be addressed.
Molecules 2016, 21(2), 228; https://doi.org/10.3390/molecules21020228
Submission received: 21 January 2016 / Revised: 4 February 2016 / Accepted: 4 February 2016 / Published: 18 February 2016
(This article belongs to the Section Medicinal Chemistry)
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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: imidazole; nitrogen heterocycles; coumarin; hepatitis C virus; structure–activity relationships imidazole; nitrogen heterocycles; coumarin; hepatitis C virus; structure–activity relationships
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MDPI and ACS Style

Tsay, S.-C.; Lin, S.-Y.; Huang, W.-C.; Hsu, M.-H.; Hwang, K.C.; Lin, C.-C.; Horng, J.-C.; Chen, I.-C.; Hwu, J.R.; Shieh, F.-K.; et al. Synthesis and Structure-Activity Relationships of Imidazole-Coumarin Conjugates against Hepatitis C Virus. Molecules 2016, 21, 228. https://doi.org/10.3390/molecules21020228

AMA Style

Tsay S-C, Lin S-Y, Huang W-C, Hsu M-H, Hwang KC, Lin C-C, Horng J-C, Chen I-C, Hwu JR, Shieh F-K, et al. Synthesis and Structure-Activity Relationships of Imidazole-Coumarin Conjugates against Hepatitis C Virus. Molecules. 2016; 21(2):228. https://doi.org/10.3390/molecules21020228

Chicago/Turabian Style

Tsay, Shwu-Chen, 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, and et al. 2016. "Synthesis and Structure-Activity Relationships of Imidazole-Coumarin Conjugates against Hepatitis C Virus" Molecules 21, no. 2: 228. https://doi.org/10.3390/molecules21020228

APA Style

Tsay, S.-C., Lin, S.-Y., Huang, W.-C., Hsu, M.-H., Hwang, K. C., Lin, C.-C., Horng, J.-C., Chen, I.-C., Hwu, J. R., Shieh, F.-K., Leyssen, P., & Neyts, J. (2016). Synthesis and Structure-Activity Relationships of Imidazole-Coumarin Conjugates against Hepatitis C Virus. Molecules, 21(2), 228. https://doi.org/10.3390/molecules21020228

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