European journal of medicinal chemistry, 2014-07, Vol.82, p.459-465
2014
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Details
- Autor(en) / Beteiligte
- Titel
- Microwave-assisted synthesis of C-8 aryl and heteroaryl inosines and determination of their inhibitory activities against Plasmodium falciparum purine nucleoside phosphorylase
- Ist Teil von
- European journal of medicinal chemistry, 2014-07, Vol.82, p.459-465
- Ort / Verlag
- France: Elsevier Masson SAS
- Erscheinungsjahr
- 2014
- Quelle
- ScienceDirect
- Beschreibungen/Notizen
- 8-Arylinosines have been scarcely studied for therapeutic purposes, probably due to difficulties in their synthesis. The recently described direct arylation reaction at position 8 of purine nucleosides has been employed to synthesize a series of 8-aryl and 8-pyridylinosines. These compounds have been studied for hydrolytic stability and subjected to biological evaluation. Three compounds have shown a pronounced specific inhibition of Plasmodium falciparum-encoded purine nucleoside phosphorylase, an important target for antimalarial chemotherapy. [Display omitted] •Novel 8-aryl and pyridyl inosines have been synthesized by a direct arylation reaction mediated by Pd/Cu complexes.•Extensive Quadrasil MP treatment has allowed removal of metal contaminants.•Several aryl inosines selectively inhibited Plasmodium falciparum PNP but not human or prokaryotic PNPs.
- Sprache
- Englisch
- Identifikatoren
- ISSN: 0223-5234eISSN: 1768-3254DOI: 10.1016/j.ejmech.2014.05.073Titel-ID: cdi_proquest_miscellaneous_1542004430
- Format
- –
- Schlagworte
- Animals, Anti-Bacterial Agents - chemical synthesis, Anti-Bacterial Agents - chemistry, Anti-Bacterial Agents - pharmacology, Antiviral, Antiviral Agents - chemical synthesis, Antiviral Agents - chemistry, Antiviral Agents - pharmacology, Cell Line, Tumor, Cercopithecus aethiops, Direct C-arylation, DNA Viruses - drug effects, Dogs, Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, Enzyme Inhibitors - chemical synthesis, Enzyme Inhibitors - chemistry, Enzyme Inhibitors - pharmacology, Escherichia coli - drug effects, HeLa Cells, Humans, Inosine, Inosine - analogs & derivatives, Inosine - chemical synthesis, Inosine - pharmacology, Madin Darby Canine Kidney Cells, Microbial Sensitivity Tests, Microwave-assisted synthesis, Microwaves, Molecular Conformation, Mycoplasma hyorhinis - drug effects, Phosphorylase, Plasmodium falciparum - enzymology, Purine-Nucleoside Phosphorylase - antagonists & inhibitors, Purine-Nucleoside Phosphorylase - metabolism, RNA Viruses - drug effects, Vero Cells