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Tenofovir disoproxil fumarate

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Identification
Molecular formula
C9H14N5O4P
CAS number
202138-50-9
IUPAC name
[[5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]methylphosphonic acid
State
State

At room temperature, the compound is in a solid state.

Melting point (Celsius)
180.00
Melting point (Kelvin)
453.15
Boiling point (Celsius)
800.00
Boiling point (Kelvin)
1 073.15
General information
Molecular weight
287.21g/mol
Molar mass
287.2130g/mol
Density
2.5000g/cm3
Appearence

The compound is generally found as a white to off-white crystalline solid.

Comment on solubility

Solubility Characteristics of [5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]methylphosphonic acid

The solubility of [5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]methylphosphonic acid (C9H14N5O4P) is influenced by several key factors. Here are some important points to consider:

  • Polar Nature: The presence of multiple hydroxyl (-OH) groups and a phosphonic acid group contributes to a significant polar character, which generally enhances solubility in polar solvents like water.
  • Hydrogen Bonding: The ability of the compound to engage in hydrogen bonding further increases its affinity for aqueous solutions, promoting dissociation and solvation.
  • Structural Complexity: The intricate structure, characterized by both cyclic and linear components, may lead to variable solubility depending on the formulation and environmental conditions.
  • pH Dependence: The solubility can also be influenced by the pH of the solution, where changes may lead to protonation or deprotonation of functional groups.

Overall, one might expect this compound to have reasonable solubility in aqueous solutions, though practical measurements would be necessary to determine exact values. As is often the case with complex organic molecules, experimental data may reveal specific interactions that could influence solubility significantly. Furthermore, it is prudent to conduct solubility studies under varying conditions to understand how the factors mentioned above interplay in real-world scenarios.

Interesting facts

Interesting Facts about [5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]methylphosphonic acid

This unique compound is a fascinating example of a synthetic analog that combines structural features important in biochemistry and medicinal chemistry. Here are some intriguing aspects:

  • Phosphonic Acid Derivative: This compound belongs to the class of phosphonic acids, which are known for their ability to mimic natural phosphate esters, making them significant in enzymatic reactions and biological systems.
  • Structural Complexity: The presence of multiple functional groups—including amino, hydroxyl, and methoxy groups—highlights its potential for diverse interactions with biological macromolecules, such as proteins and nucleic acids.
  • Potential Applications: Compounds like this one have potential utility in drug design, particularly in antiviral and anticancer therapies, due to their ability to interact with key biological pathways.
  • Role of Purine Analog: The incorporation of the purine base serves as a critical feature for cellular uptake and biological activity, drawing parallels to naturally occurring nucleotides which are essential for DNA and RNA synthesis.
  • Research Interest: Due to its complex nature and potential biological relevance, this compound might be an object of study in fields such as medicinal chemistry, pharmacology, and biotechnology.

As we delve deeper into the properties and applications of such compounds, it becomes evident how synthetic chemistry can create tools that mimic and potentially enhance natural biological processes. Whether in the lab or in clinical research, the role of compounds like this one continues to expand our understanding of chemistry in biological contexts.

Synonyms
NSC614641
CHEMBL2002441
SCHEMBL21724956
NCI60_004946
NS00046487