Gemcitabine

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Identification

Molecular formula
C9H11F N3O4
CAS Number
95058-81-4
IUPAC Name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione
Molecular Weight
299.19g/mol
Melting Point
(Celsius)
Boiling Point
(Celsius)
Density
1.7125g/cm3
Synonyms
doxifluridine
Interesting facts

Interesting Facts about 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione

This compound presents a fascinating blend of organic chemistry and biological significance. It belongs to a class of compounds known for their role in pharmaceutical applications. Here are some interesting facts:

  • Structural Uniqueness: The compound features a complex structure that includes a tetrahydrofuran ring fused with a pyrimidine moiety. This unique combination enhances its reactivity and interaction with biological targets.
  • Biological Relevance: Compounds like this are often designed to inhibit enzymes or act on specific receptors in living organisms, making them crucial elements in drug discovery programs.
  • Stereochemistry: The stereochemistry represented by the (2R,3R,4S,5R) configuration is vital. In medicinal chemistry, subtle changes in stereochemistry can lead to significant changes in biological activity.
  • Fluorine Incorporation: The presence of the fluorine atom in the structural formula enhances lipophilicity, which can improve the compound's ability to cross biological membranes and reach its targets.
  • Potential Applications: Due to its complex nature, this compound could be explored in various therapeutic contexts, particularly within the realm of oncology, where pyrimidine derivatives have been studied for their antitumor properties.

In summary, 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione exemplifies the intricate relationship between chemical structure and biological function. Its study is not only a testament to the principles of organic synthesis but also to the ongoing efforts to develop effective therapeutic agents.

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