- Stereoselective synthesis of 4′-selenonucleosides using the Pummerer glycosylation reaction
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The syntheses of four selenonucleosides, namely 4′-β-selenoadenosine, -cytidine, -thymidine, and -uridine are described. Commercially available d-ribonolactone was converted to the key intermediate 1,4-anhydro-4-seleno-d-ribitol in seven steps in overall excellent yield. Oxidation of the seleno-d-ribitol with MCPBA gave a single diastereomeric selenoxide in excellent yield, which upon Pummerer reaction in the presence of silylated purine or pyrimidine bases gave stereoselectively the corresponding 4′-β-selenonucleosides. The stereochemistry at the anomeric center was determined by means of 1D-NOE experiments.
- Jayakanthan, Kumarasamy,Johnston, Blair D.,Pinto, B. Mario
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- ANTIVIRAL AZASUGAR-CONTAINING NUCLEOSIDES
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Disclosed are compounds comprising an azasugar attached to a heterocyclic base, including pharmaceutically acceptable salts thereof, suitable for use in inhibiting viral RNA polymerase activity or viral replication, and treating viral infections. The compounds are characterized, in part, by favorable pharmacokinetics for the active pharmaceutical ingredient, particularly in conjunction with enteral administration, including, in particular, oral administration. Also disclosed are pharmaceutical compositions comprising one or more compounds mentioned above, or pharmaceutically acceptable salts thereof, as well as methods for preparing same. Also provided are methods for inhibiting viral RNA polymerase activity, viral replication, and treating viral infections.
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- RIBONUCLEIC ACIDs WITH 4'-THIO-MODIFIED NUCLEOTIDES AND RELATED METHODS
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Disclosed are messenger RNA molecules and related compositions incorporating a 4'-thio modification in the furanose ring of at least one nucleotide residue, and methods of using these mRNAs to produce an encoded therapeutic protein invivo and to treat or prevent diseases or disorders. In certain embodiments, the 4'-thio modified mRNA provides for enhanced stability and/or reduced immunogenicity in in vivo therapies.
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- One-pot tandem strecker reaction and iminocyclisations: Syntheses of trihydroxypiperidine α-iminonitriles
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Unbranched, and α- and β-methyl-branched, trihydroxypiperidine α-iminonitriles have been obtained in a single step from protected 5-O-tosylate pentoses. This reaction comprises a one-pot tandem Strecker reaction and iminocyclisation. These trihydroxypiper
- Ayers, Benjamin J.,Fleet, George W.J.
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p. 2053 - 2069
(2014/04/17)
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- COMPOSITIONS AND METHODS FOR INHIBITING VIRAL POLYMERASE
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Provided are compounds of Formula (I) as described herein. Compounds of Formula (I) are useful in methods of inhibiting viral RNA polymerase activity and viral replication. Also provided are pharmaceutical compositions comprising compounds of Formula (I), as well as methods of treating viral infections using compounds of Formula (I).
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