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5-Fluorouracil (F-ara-AMP)

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Identification
Molecular formula
C4H3FN2O2
CAS number
51-21-8
IUPAC name
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-fluoro-pyrimidin-2-one
State
State

At room temperature, 5-Fluorouracil is typically a solid substance. It is often used in its crystalline powder form in pharmaceutical applications.

Melting point (Celsius)
282.00
Melting point (Kelvin)
555.20
Boiling point (Celsius)
316.50
Boiling point (Kelvin)
589.70
General information
Molecular weight
130.08g/mol
Molar mass
130.0770g/mol
Density
1.5517g/cm3
Appearence

5-Fluorouracil typically appears as a white to off-white powder. It is crystalline in form and has a distinct appearance due to the presence of the fluorine atom, which contributes to its unique properties among pyrimidine analogues.

Comment on solubility

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

The complex structure of 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-fluoro-pyrimidin-2-one presents intriguing characteristics regarding its solubility. Understanding solubility is crucial as it affects the compound's bioavailability and overall application potential. Here are some key points to consider:

  • Polar Nature: Due to the presence of multiple hydroxyl (-OH) groups in its structure, this compound is likely to exhibit increased polarity. Such characteristics generally enhance solubility in polar solvents like water.
  • Hydrogen Bonding: The ability to form hydrogen bonds is prominent in compounds with -OH groups. This not only facilitates solubility in polar solvents but also suggests a potential for intermolecular interactions that could influence solubility under various conditions.
  • Hydrophobic Domains: While the hydroxyl groups promote solubility, the presence of the fluoro group and the pyrimidine ring might introduce some hydrophobic properties. This dual characteristic may lead to variable solubility, especially in mixed solvent environments.
  • pH Dependence: The ionization state of the amino group can alter the solubility based on the pH of the solution, potentially increasing solubility in an acidic environment where the amino group is protonated.

In summary, while the solubility of 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-fluoro-pyrimidin-2-one is likely influenced by both polar and non-polar characteristics, precise solubility data would require empirical testing under controlled conditions to fully understand its behavior in various solvents.

Interesting facts

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

This compound, often appreciated in the field of medicinal chemistry, belongs to a class of molecules known for their biological activity. Here are some key highlights about this interesting molecule:

  • Structure and Chirality: The molecule features a complex chiral center, specifically at the tetrahydrofuran ring, contributing to its unique properties and interactions within biological systems.
  • Pharmacological Potential: Compounds with similar structures are often investigated for their potential as antiviral or anticancer agents, illustrating the significance of this compound in drug discovery.
  • Fluorine's Role: The presence of a fluorine atom in the pyrimidine ring enhances metabolic stability and can significantly improve the binding affinity towards target enzymes or receptors, an essential aspect in the design of pharmaceuticals.
  • Sugar-Like Moiety: The inclusion of a sugar-like structure such as the 3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran promotes the idea of "mimicking" natural substrates, aiding in better cellular uptake and activity.
  • Research and Applications: Many researchers are drawn to explore the structure-activity relationships of molecules like this, with a goal to design newer variants that exhibit enhanced efficacy and reduced toxicity profiles.

In conclusion, the exploration of compounds like 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-fluoro-pyrimidin-2-one is a testament to the intricate connection between chemical structure and biological functionality, showcasing the endless possibilities within the realm of organic and medicinal chemistry.

Synonyms
Ara-fluorocytosine
4298-10-6
5-Fluorocytosine arabinoside
Arafluorocytosine
1-beta-D-Arabinofuranosyl-5-fluorocytosine
87PGS3A0AZ
beta-D-Arabinofuranosyl-5-fluorocytosine
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidin-2-one
Ara-FC
Fluorocytosine arabinoside
2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-5-fluoro-
NSC-529180
FCA
.beta.-D-Arabinofuranosyl-5-fluorocytosine
NSC 529180
1-.beta.-D-Arabinofuranosyl-5-fluorocytosine
Cytosine, 1-.beta.-D-arabinofuranosyl-5-fluoro-
5-F-Ara-C
UNII-87PGS3A0AZ
CYTOSINE, 1-beta-D-ARABINOFURANOSYL-5-FLUORO-
SCHEMBL1230711
DTXSID00195602
STRZQWQNZQMHQR-MNCSTQPFSA-N
5-FLUORO-ARABINOSYLCYTOSINE
2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl- 5-fluoro-
AKOS040750559
5-fluoro-1-beta-D-arabinofuranosylcytosine
Q27269833
2(1H)-PYRIMIDINONE, 4-AMINO-1-.BETA.-D-ARABINOFURANOSYL-5-FLUORO-
4-Amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-fluoropyrimidin-2(1H)-one
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-fluoro-pyrimidin-2-one