Coumarins hinged directly on benzimidazoles and their ribofuranosides to inhibit hepatitis C virus

Shwu Chen Tsay, Jih Ru Hwu, Raghunath Singha, Wen Chieh Huang, Yung Hsiung Chang, Ming-Hua Hsu, Fa Kuen Shieh, Chun Cheng Lin, Kuo Chu Hwang, Jia Cherng Horng, Erik De Clercq, Inge Vliegen, Johan Neyts

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

A new compound library that contained 20 hinged benzimidazole-coumarin hybrids and their β-d-ribofuranosides was established. The anti-hepatitis C virus (HCV) activity of all novel coumarin derivatives, which were obtained by use of organic synthetic methods, was tested. Two of these hybrids exhibited appealing EC50 values of as low as 3.0 and 5.5 μM. The best selectivity index was 14. The incorporation of a d-ribofuranose into the hinged hybrids provided the corresponding nucleosides with the β configuration, one of which inhibited HCV replication with an EC50 value of 20 μM. Additionally, the structure-activity relationship is elucidated on the basis of the functional groups that were attached to the nuclei of benzimidazole, coumarin, and ribofuranose of the hybrids.

Original languageEnglish
Pages (from-to)290-298
Number of pages9
JournalEuropean Journal of Medicinal Chemistry
Volume63
DOIs
Publication statusPublished - 2013 Mar 18

Fingerprint

Benzimidazoles
Coumarins
Viruses
Hepacivirus
Nucleosides
Functional groups
Structure-Activity Relationship
Virus Replication
Libraries
coumarin
benzimidazole

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cite this

Tsay, Shwu Chen ; Hwu, Jih Ru ; Singha, Raghunath ; Huang, Wen Chieh ; Chang, Yung Hsiung ; Hsu, Ming-Hua ; Shieh, Fa Kuen ; Lin, Chun Cheng ; Hwang, Kuo Chu ; Horng, Jia Cherng ; De Clercq, Erik ; Vliegen, Inge ; Neyts, Johan. / Coumarins hinged directly on benzimidazoles and their ribofuranosides to inhibit hepatitis C virus. In: European Journal of Medicinal Chemistry. 2013 ; Vol. 63. pp. 290-298.
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abstract = "A new compound library that contained 20 hinged benzimidazole-coumarin hybrids and their β-d-ribofuranosides was established. The anti-hepatitis C virus (HCV) activity of all novel coumarin derivatives, which were obtained by use of organic synthetic methods, was tested. Two of these hybrids exhibited appealing EC50 values of as low as 3.0 and 5.5 μM. The best selectivity index was 14. The incorporation of a d-ribofuranose into the hinged hybrids provided the corresponding nucleosides with the β configuration, one of which inhibited HCV replication with an EC50 value of 20 μM. Additionally, the structure-activity relationship is elucidated on the basis of the functional groups that were attached to the nuclei of benzimidazole, coumarin, and ribofuranose of the hybrids.",
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Tsay, SC, Hwu, JR, Singha, R, Huang, WC, Chang, YH, Hsu, M-H, Shieh, FK, Lin, CC, Hwang, KC, Horng, JC, De Clercq, E, Vliegen, I & Neyts, J 2013, 'Coumarins hinged directly on benzimidazoles and their ribofuranosides to inhibit hepatitis C virus', European Journal of Medicinal Chemistry, vol. 63, pp. 290-298. https://doi.org/10.1016/j.ejmech.2013.02.008

Coumarins hinged directly on benzimidazoles and their ribofuranosides to inhibit hepatitis C virus. / Tsay, Shwu Chen; Hwu, Jih Ru; Singha, Raghunath; Huang, Wen Chieh; Chang, Yung Hsiung; Hsu, Ming-Hua; Shieh, Fa Kuen; Lin, Chun Cheng; Hwang, Kuo Chu; Horng, Jia Cherng; De Clercq, Erik; Vliegen, Inge; Neyts, Johan.

In: European Journal of Medicinal Chemistry, Vol. 63, 18.03.2013, p. 290-298.

Research output: Contribution to journalArticle

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AU - Neyts, Johan

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