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Azidothymidine (AZT)

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Identification
Molecular formula
C10H13N5O4
CAS number
30516-87-1
IUPAC name
[3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
State
State

Azidothymidine is typically a solid at room temperature, presenting as a crystalline powder.

Melting point (Celsius)
125.00
Melting point (Kelvin)
398.00
Boiling point (Celsius)
689.90
Boiling point (Kelvin)
964.90
General information
Molecular weight
267.24g/mol
Molar mass
267.2410g/mol
Density
1.6500g/cm3
Appearence

Azidothymidine, also known as AZT, typically appears as a white to off-white crystalline powder. It is hygroscopic and its crystal structure can form needles or prisms.

Comment on solubility

Solubility of [3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate

The solubility of the compound C10H13N5O4 can be influenced by several factors, given its unique structure comprising both organic and inorganic elements. Here are some key points to consider:

  • Solvent Interaction: The presence of the phosphate group typically enhances the solubility in polar solvents such as water, due to its ability to form hydrogen bonds.
  • Hydrophilicity vs. Hydrophobicity: The compound exhibits a mix of hydrophilic (phosphate) and hydrophobic regions (alkyl and aromatic components), which can complicate solubility predictions.
  • Effect of pH: The solubility may vary with changes in pH, as the protonation state of the phosphate can significantly affect its solubility characteristics.
  • Concentration Dependency: At higher concentrations, solubility may be further reduced due to potential aggregation or precipitation of the more hydrophobic parts of the molecule.

In conclusion, while the phosphate moiety suggests a propensity for solubility in polar environments, the overall solubility of C10H13N5O4 is subject to various factors, making experimental investigation necessary for precise characterization. As one might say, "the devil is in the details," particularly when discussing the solubility of complex compounds.

Interesting facts

Interesting Facts about [3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate

This intriguing compound presents a fascinating combination of functional groups and structural features that make it a subject of interest in the field of medicinal chemistry. Here are some notable aspects:

  • Azido Group: The presence of the azido group (-N₃) is significant, as azides are known for their reactivity and potential applications in click chemistry, a powerful tool for synthesizing complex molecules.
  • Pyrimidine Derivative: This compound incorporates a pyrimidine ring, which is a common motif in various biological molecules, including nucleic acids. Its analogs are often evaluated for their pharmacological properties.
  • Tetrahydrofuran Inclusion: The inclusion of the tetrahydrofuran moiety adds another layer of complexity. Compounds containing this cyclic ether are known for their stability and solubilizing properties in organic synthesis.
  • Potential Biological Activity: Compounds with similar structural features have shown promise in various biological assays, indicating that this compound could have interesting potential as a drug candidate.
  • Phosphate Group: The dihydrogen phosphate component is known to play essential roles in biochemistry, particularly in energy transfer and regulation of metabolic pathways through its involvement in ATP metabolism.

In summary, [3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate stands out due to its intricate combination of functional groups, offering numerous avenues for research and application. As we continue to explore the bioactivity and synthetic pathways of such compounds, the potential for new discoveries in drug development and biochemistry remains vast.

Synonyms
3'-AZIDO-2',3'-DIDEOXY-THYMIDINE-5'-MONOPHOSPHATE, SODIUM SALT