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Synthesis and antiviral activity of novel anomeric branched carbocyclic nucleosides

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Abstract

Novel anomeric branched carbocyclic nucleosides were synthesized from 1,3-dihydroxy acetone. 4′-Hydroxymethyl was installed by [3,3]-sigmatropic rearrangement reaction and 1′-methyl group was introduced by carbonyl addition of methylmagnesium bromide. The coupling of nucleosidic bases and desilylation afforded a series of novel nucleosides. The synthesized compounds16–19 were evaluated for their antiviral activity against HIV-1, HSV-1, HSV-2, and EMCV. Compounds16 and19 exhibit toxicity non-related to any anti-HIV-1 activity.

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Correspondence to Joon Hee Hong.

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Kim, A., Hong, J.H. Synthesis and antiviral activity of novel anomeric branched carbocyclic nucleosides. Arch Pharm Res 28, 1105–1110 (2005). https://doi.org/10.1007/BF02972969

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