Cytostatic and antiviral 6-arylpurine ribonucleosides. Part 7: synthesis and evaluation of 6-substituted purine l-ribonucleosides
Language English Country England, Great Britain Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
16905315
DOI
10.1016/j.bmcl.2006.07.092
PII: S0960-894X(06)00885-7
Knihovny.cz E-resources
- MeSH
- Antiviral Agents chemical synthesis chemistry pharmacology MeSH
- HeLa Cells MeSH
- Hepacivirus drug effects MeSH
- HL-60 Cells MeSH
- Humans MeSH
- Microbial Sensitivity Tests MeSH
- Molecular Structure MeSH
- Mice MeSH
- Cell Line, Tumor MeSH
- Cell Proliferation drug effects MeSH
- Antineoplastic Agents chemical synthesis chemistry pharmacology MeSH
- Purine Nucleosides chemical synthesis chemistry pharmacology MeSH
- Ribonucleosides chemical synthesis chemistry pharmacology MeSH
- Drug Screening Assays, Antitumor MeSH
- In Vitro Techniques 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
- Antineoplastic Agents MeSH
- Purine Nucleosides MeSH
- Ribonucleosides MeSH
A series of purine l-ribonucleosides 2a-2i bearing diverse C-substituents (alkyl, aryl, hetaryl or hydroxymethyl) in the position 6 were prepared by Pd-catalyzed cross-coupling reactions of 6-chloro-9-(2,3,5-tri-O-acetyl-beta-l-ribofuranosyl)purine with the corresponding organometallics followed by deprotection. Unlike their d-ribonucleoside enantiomers that possess strong cytostatic and anti-HCV activity, the l-ribonucleosides were inactive except for 6-benzylpurine nucleoside 2h showing moderate anti-HCV effect in replicon assay. A triphosphate of 2h did not inhibit HCV RNA polymerase.
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