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Brivudine

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Identification
Molecular formula
C11H13BrN2O5
CAS number
69304-47-8
IUPAC name
4-amino-5-bromo-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
State
State

Solid

Melting point (Celsius)
187.00
Melting point (Kelvin)
460.15
Boiling point (Celsius)
360.00
Boiling point (Kelvin)
633.15
General information
Molecular weight
355.14g/mol
Molar mass
355.1520g/mol
Density
2.2000g/cm3
Appearence

White to off-white crystalline powder.

Comment on solubility

Solubility of 4-amino-5-bromo-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one

The solubility of 4-amino-5-bromo-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one is influenced by several factors:

  • Polarity: The compound features multiple functional groups, such as amino and hydroxy groups, which tend to enhance its polarity, potentially leading to increased solubility in polar solvents like water.
  • Hydrogen Bonding: The presence of hydroxymethyl and hydroxyl groups facilitates hydrogen bonding with solvents, which can also aid in the solubility of this compound.
  • Temperature: Solubility may be temperature-dependent; generally, higher temperatures can increase the solubility of solid compounds in liquids.
  • pH Sensitivity: The solubility may vary with pH, especially due to the amino group that could accept protons, affecting the ionization state and thus the solubility in aqueous environments.

Additionally, it is important to consider that solubility in organic solvents may differ significantly from aqueous solubility. In practical applications, the solubility characteristics can guide how this compound is utilized in pharmaceutical formulations and chemical processes.

In summary, the solubility of this complex compound is not straightforward and depends on various physico-chemical factors. It emphasizes the necessity of conducting experimental evaluations to determine precise solubility under specific conditions.

Interesting facts

Interesting Facts about 4-amino-5-bromo-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one

This compound is a fascinating example of a pyrimidine derivative, which plays a critical role in the realm of medicinal chemistry. Pyrimidines are essential building blocks in biochemistry, as they are fundamental components of nucleic acids, specifically DNA and RNA.

1. Structural Significance

  • Pyrimidine Core: The pyrimidine ring provides the framework for many biologically active molecules, making it vital in drug design.
  • Chiral Centers: The presence of chirality in the tetrahydrofuran moiety introduces variation in biological activity, allowing for the exploration of different stereoisomers.

2. Biological Relevance

This compound is particularly noteworthy for its potential applications in pharmaceuticals. The bromine substituent can enhance the compound's interactions with biological targets, making it a promising candidate for:

  • Antiviral agents
  • Antitumor therapies
  • Enzyme inhibitors

3. Synthetic Pathways

The synthesis of this compound can involve multiple steps, showcasing various synthetic strategies, including:

  • Nucleophilic substitution reactions
  • Protection-deprotection strategies for functional groups
  • Coupling reactions to introduce the tetrahydrofuran unit

4. Interactions and Mechanisms

Researchers often study the molecular interactions of pyrimidine derivatives with enzymes and receptors, allowing for the understanding of their mechanisms of action. This compound could exhibit:

  • Inhibition of specific enzymes involved in nucleotide metabolism
  • Antagonism of certain receptors

In conclusion, the compound 4-amino-5-bromo-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one is a compound delight for chemists and biochemists alike, blending the intricacies of organic synthesis, molecular biology, and potential therapeutic applications. Exploring its properties further might unveil new pathways for innovative treatments and deepen our understanding of pyrimidine chemistry.

Synonyms
SCHEMBL198512
HY-W011376