Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: efficient synthesis and antiviral activity
Language English Country England, Great Britain Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
21745746
PubMed Central
PMC7125515
DOI
10.1016/j.bmc.2011.06.045
PII: S0968-0896(11)00485-8
Knihovny.cz E-resources
- MeSH
- Antiviral Agents chemical synthesis chemistry pharmacology MeSH
- Cell Line MeSH
- Herpes Simplex drug therapy MeSH
- HIV Infections drug therapy MeSH
- HIV drug effects MeSH
- Humans MeSH
- Mice MeSH
- Nucleosides chemical synthesis chemistry pharmacology MeSH
- Organophosphonates chemical synthesis chemistry pharmacology MeSH
- Simplexvirus drug effects MeSH
- Vaccinia drug therapy MeSH
- Cell Survival drug effects MeSH
- Virus Diseases drug therapy MeSH
- Vaccinia virus drug effects MeSH
- Viruses drug effects MeSH
- Structure-Activity Relationship MeSH
- Animals MeSH
- Check Tag
- Humans MeSH
- Mice MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Antiviral Agents MeSH
- Nucleosides MeSH
- Organophosphonates MeSH
Series of novel acyclic nucleoside phosphonates (ANPs) with various nucleobases and 2-(2-phosphonoethoxy)ethyl (PEE) chain bearing various substituents in β-position to the phosphonate moiety were prepared. The influence of structural alternations on antiviral activity was studied. Several derivatives exhibit antiviral activity against HIV and vaccinia virus (middle micromolar range), HSV-1 and HSV-2 (lower micromolar range) and VZV and CMV (nanomolar range), although the parent unbranched PEE-ANPs are inactive. Adenine as a nucleobase and the methyl group attached to the PEE chain proved to be a prerequisite to afford pronounced antiviral activity.
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