5′-Noraristeromycin derivatives isomeric to aristeromycin and 2′-deoxyaristeromycin |
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Authors: | Xue-qiang Yin |
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Institution: | Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849, USA |
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Abstract: | A straightforward synthesis of (1S,2R,3R,4R)-4-(6-aminopurin-9-yl)-2-hydroxymethylcyclopentane-1,3-diol (2), an isomer of aristeromycin, and its 2′-deoxy derivative 3 from readily available disubstituted cyclopentenes is presented. An antiviral analysis of 2 showed it to have significant activity versus Epstein-Barr virus (IC50 0.62 μg/mL in the Elisa assay) and to be free of cytotoxicity effects against the host cells. In a much less comprehensive antiviral analysis, 3 also was active towards Epstein-Barr (IC50 7.58 μg/mL in the Elisa assay) but this was accompanied by cellular toxicity. |
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Keywords: | 3&prime -Homo carbocylic nucleosides Epoxide ring opening Mitsunobu reaction |
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