3-Carbamoyl-1-beta-D-ribofuranosylpyridinium chloride
[CAS# 23111-00-4]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: 3-Carbamoyl-1-beta-D-ribofuranosylpyridinium chloride
• Synonyms: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridin-1-ium-3-carboxamide chloride
• Molecular Formula: C₁₁H₁₅N₂O₅.Cl
• Molecular Weight: 290.70
• Protein Sequence: v
• CAS Registry Number: 23111-00-4
• EC Number: 807-820-5
• SMILES: C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N.[Cl-]

Properties

• Solubility: 10 mg/mL (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

3-Carbamoyl-1-beta-D-ribofuranosylpyridinium chloride is a chemical compound belonging to the class of pyridinium derivatives with a ribofuranosyl sugar moiety and a carbamoyl functional group. This compound is of interest due to its structural relation to nucleoside analogs, which have significant applications in medicinal chemistry, especially in antiviral and anticancer drug development. The pyridinium ring system confers a positive charge, making the molecule a quaternary ammonium salt, which can influence its solubility and biological interactions.

The discovery of this compound type typically stems from efforts to modify nucleosides for enhanced biological activity or pharmacokinetic properties. By attaching a carbamoyl group and a ribose sugar to the pyridinium nucleus, researchers aim to create molecules that can interact with enzymes or receptors involved in nucleotide metabolism or nucleic acid synthesis. Such compounds can serve as inhibitors or substrates mimicking natural nucleosides, potentially interfering with viral replication or cancer cell proliferation.

Applications of 3-carbamoyl-1-beta-D-ribofuranosylpyridinium chloride and related analogs have primarily focused on their use as building blocks in the synthesis of nucleotide analogs for therapeutic purposes. These compounds can be incorporated into nucleic acids or enzymatic pathways, altering the normal function of nucleotides and exerting antiviral or cytotoxic effects. Research continues to explore the optimization of these molecules for improved selectivity and reduced toxicity.

Despite the chemical significance, there is limited specific literature focused solely on 3-carbamoyl-1-beta-D-ribofuranosylpyridinium chloride. Most knowledge derives from studies on related pyridinium nucleoside analogs and their biochemical properties. Further studies are needed to fully elucidate its pharmacological potential and applications.

References

References

Makarov MV, Grachev AA, Makarova SS et al. (2019) Syntheses and chemical properties of β‑nicotinamide riboside derivatives. Beilstein Journal of Organic Chemistry 15 36 1–19 DOI: 10.3762/bjoc.15.36

Hayat F, Belenky M, Brenner C (2024) Synthesis, detection, and metabolism of pyridone ribosides and oxidized NAD analogs. Chemical Research in Toxicology 37 7 1234–1245 DOI: 10.1021/acs.chemrestox.3c00264