| Literature DB >> 17977606 |
Jih Ru Hwu1, Raghunath Singha, Shih Ching Hong, Yung Hsiung Chang, Asish R Das, Inge Vliegen, Erik De Clercq, Johan Neyts.
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 3.4 microM and 4.1 microM, respectively. At a concentration of 5.0 microM, compound 7c inhibited HCV RNA replication by 90% and had no effect on cell proliferation. Given these data, a structure-activity relationship was established.Entities:
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Year: 2007 PMID： 17977606 DOI： 10.1016/j.antiviral.2007.09.003
Source DB: PubMed Journal: Antiviral Res ISSN： 0166-3542 Impact factor: 5.970