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Cytosine arabinoside

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Identification
Molecular formula
C9H13N3O5
CAS number
147-94-4
IUPAC name
5-amino-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
State
State

At room temperature, Cytosine arabinoside is typically in a solid state, specifically as a crystalline powder. It is stable under standard conditions of temperature and pressure.

Melting point (Celsius)
214.00
Melting point (Kelvin)
487.15
Boiling point (Celsius)
985.00
Boiling point (Kelvin)
1 258.15
General information
Molecular weight
243.22g/mol
Molar mass
243.2170g/mol
Density
1.6903g/cm3
Appearence

Cytosine arabinoside appears as a white to off-white crystalline powder. It is often used in its lyophilized form for pharmaceutical applications. The compound is hygroscopic and should be stored in a dry environment to maintain its stability.

Comment on solubility

Solubility of 5-amino-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione (C9H13N3O5)

The solubility of 5-amino-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione is an essential characteristic that influences its biological activity and potential applications. Due to its complex structure, solubility can be affected by various factors:

  • Functional Groups: The presence of multiple hydroxyl (-OH) groups and an amino (-NH2) group typically enhances solubility in polar solvents such as water.
  • pH Influence: The solubility may vary with pH; compounds with amino groups can become more protonated in acidic conditions, increasing their solubility.
  • Hydration Effects: Hydrogen bonding between water molecules and the compound can contribute significantly to solubility.

As a result, this compound is expected to exhibit good solubility in aqueous environments, potentially enabling effective uptake in biological systems. However, it's important to consider that solubility is not only a function of molecular structure, but also of environmental conditions. Thus, the solubility characteristics should be thoroughly evaluated in relevant solvents and under various conditions.

Interesting facts

Interesting Facts about 5-amino-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

This compound, often abbreviated as AHT, has garnered significant attention in the field of medicinal chemistry due to its intriguing structural features and potential biological applications. Here are some fascinating insights:

  • Biosynthetic Pathways: AHT bears resemblance to various nucleic acid components, which may suggest potential roles in biosynthetic pathways that involve nucleotides.
  • Antiviral Activity: Preliminary studies have indicated that compounds similar to AHT may exhibit antiviral properties, making them promising candidates for drug development against viral infections.
  • Enzyme Inhibition: Research demonstrates that this compound may inhibit certain enzymes crucial for viral replication, which is a common target in pharmacology.
  • Structure-Activity Relationship (SAR): The unique arrangement of the hydroxymethyl group and the tetrahydrofuran moiety can significantly impact the biological activity of AHT, making its understanding crucial for future modifications.
  • Potential as a Chemotherapeutic Agent: Due to its chemical structure, AHT may hold promise in the development of chemotherapeutic agents, particularly in targeting specific pathways in cancer cells.

As a compound that bridges the realms of organic synthesis and pharmacology, 5-amino-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione continues to be a topic of extensive research. Emphasizing its potential, scientists often say, "A single molecule can unlock new avenues of therapy." This highlights the exciting possibilities that compounds like AHT hold in the future of medicine.

Synonyms
CHEMBL160229
5-Amino-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
5-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
BDBM50028591
5-AMINO-2'-DEOXYURIDINE FREE BASE