Title: Synthesis of new benzimidazole-coumarin conjugates as anti-hepatitis C virus agents
Authors: Hwu, JR ×
Singha, R
Hong, SC
Das, AR
Vliegen, Inge
De Clercq, Erik
Neyts, Johan #
Issue Date: Feb-2008
Publisher: Elsevier/North-Holland
Series Title: Antiviral Research vol:77 issue:2 pages:157-162
Abstract: Nineteen new conjugated compounds were successfully synthesized by a one-flask method from benzimidazole and coumarin derivatives. A methylenethio linker was used to connect these two kinds of derivatives. In addition, substituted benzimidazol-2-thiones were also coupled with beta-d-glucose peracetate; the resultant glucosides were further converted to the corresponding 2-(methylthio)coumarin derivatives. Their activity against the hepatitis C virus was tested; two of the most potent compounds 2-[(6'-bromocoumarin-3'-yl)methylenethio]-5-fluorobenzimidazole (4i) and its derivative 1-[(2'',3'',4'',6''-tetra-O-acetyl)glucopyranos-1''-yl]-2-[(6'-bromocoumarin-3'-yl)methylenethio]benzimidazole (7c) showed EC(50) values of 3.4muM and 4.1muM, respectively. At a concentration of 5.0muM, compound 7c inhibited HCV RNA replication by 90% and had no effect on cell proliferation. Given these data, a structure-activity relationship was established.
ISSN: 0166-3542
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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