Synthesis and biological evaluation of novel imidazole nucleosides as potential anti-dengue virus agents

[Display omitted] In this work, we developed imidazole nucleoside derivatives with anti-dengue virus (DENV) activity was examined. First, compounds in a nucleosides library were screened to find lead compounds which inhibit replication of DENV. As a result, 5-ethynyl-(1-β-d-ribofuranosyl)imidazole-4...

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Bibliographic Details
Published in:	Bioorganic & medicinal chemistry Vol. 27; no. 11; pp. 2181 - 2186
Main Authors:	Okano, Yuki, Saito-Tarashima, Noriko, Kurosawa, Madoka, Iwabu, Ai, Ota, Masashi, Watanabe, Tadashi, Kato, Fumihiro, Hishiki, Takayuki, Fujimuro, Masahiro, Minakawa, Noriaki
Format:	Journal Article
Language:	English
Published:	England Elsevier Ltd 01-06-2019
Subjects:	4′-Seleno-modification 4′-Thio-modification Antiviral activity Dengue virus Imidazole nucleoside Imidazole nucleoside 4′-Seleno-modification Dengue virus 4′-Thio-modification Antiviral activity
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Summary:	[Display omitted] In this work, we developed imidazole nucleoside derivatives with anti-dengue virus (DENV) activity was examined. First, compounds in a nucleosides library were screened to find lead compounds which inhibit replication of DENV. As a result, 5-ethynyl-(1-β-d-ribofuranosyl)imidazole-4-carboxamide (1; EICAR) and its 4-carbonitrile derivative EICNR (2) were selected as promising antiviral compounds. However, both of them also exhibited cytotoxicity. In order to develop an effective and less toxic compound, 4′-thio and 4′-seleno derivatives of EICAR and EICNR 3–6 were prepared. The resulting 4′-thioEICAR and 4′-thioEICNR showed inhibitory effect on DENV replication without cytotoxicity as potent as ribavirin, a positive control.
ISSN:	0968-0896 1464-3391
DOI:	10.1016/j.bmc.2019.04.015