5-Fluorouridine

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Identification

Molecular formula
C9H11FN2O6
CAS Number
316-46-1
IUPAC Name
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-fluoro-pyrimidin-2-one
Molecular Weight
264.20g/mol
Melting Point
(Celsius)
Boiling Point
(Celsius)
Density
2.3000g/cm3
Synonyms
5-Fluorocytidine
Interesting facts

4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-fluoro-pyrimidin-2-one

This intriguing compound is a complex molecule that can be classified as a modified pyrimidine derivative. Its structural elements reflect important characteristics in medicinal chemistry, particularly in the design of pharmaceuticals. Here are several fascinating aspects of this compound:

  • Fluorine's Role: The presence of the fluoro group is significant as fluorine can greatly enhance the biological activity of compounds. It often improves the metabolic stability and lipophilicity of molecules, making them more effective drugs.
  • Chiral Centers: The stereochemistry indicated by the (2R,3R,4S,5R) configuration demonstrates that this compound contains chiral centers. This feature can lead to varying biological activities; therefore, understanding and controlling stereochemistry is crucial in drug design.
  • Importance in Nucleoside Analogues: This compound’s structure resembles certain nucleosides which are vital in cellular processes and have shown promise in cancer and antiviral therapies. The ability of such compounds to mimic natural substrates can be leveraged in therapeutic applications.
  • Potential Uses: Compounds like this are often explored for their potential in treating infections, particularly viral ones. Using modified nucleobases can lead to novel mechanisms of action against resistant strains.
  • Research Utility: Being a relatively sophisticated structure, it serves as a valuable target for synthetic chemists. Challenges in its synthesis can lead to the development of new methodologies in organic chemistry.

In conclusion, the compound is a significant example of how structural modification can influence biological activity, emphasizing the interplay between chemistry and pharmacology. As researchers continue to explore its potential, it may unveil novel therapeutic pathways in the fight against various diseases.

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