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Synthesis and antiviral activity of certain second generation methylenecyclopropane nucleosides.

ABSTRACT: A second-generation series of substituted methylenecyclopropane nucleosides (MCPNs) has been synthesized and evaluated for antiviral activity against a panel of human herpesviruses, and for cytotoxicity. Although alkylated 2,6-diaminopurine analogs showed little antiviral activity, the compounds containing ether and thioether substituents at the 6-position of the purine did demonstrate potent and selective antiviral activity against several different human herpesviruses. In the 6-alkoxy series, antiviral activity depended on the length of the ether carbon chain, with the optimum chain length being about four carbon units long. For the corresponding thioethers, compounds containing secondary thioethers were more potent than those with primary thioethers.

SUBMITTER: Williams JD

PROVIDER: S-EPMC3509806 | biostudies-literature | 2012 Jun

REPOSITORIES: biostudies-literature

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Synthesis and antiviral activity of certain second generation methylenecyclopropane nucleosides.

Williams John D JD Khan Atiyya R AR Harden Emma A EA Hartline Caroll B CB Jefferson Geraldine M GM Keith Kathy A KA Prichard Mark N MN Zemlicka Jiri J Peet Norton P NP Bowlin Terry L TL

Bioorganic & medicinal chemistry 20120501 12

A second-generation series of substituted methylenecyclopropane nucleosides (MCPNs) has been synthesized and evaluated for antiviral activity against a panel of human herpesviruses, and for cytotoxicity. Although alkylated 2,6-diaminopurine analogs showed little antiviral activity, the compounds containing ether and thioether substituents at the 6-position of the purine did demonstrate potent and selective antiviral activity against several different human herpesviruses. In the 6-alkoxy series, ...[more]

PMID: 22607883

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