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Zidovudine

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Identification
Molecular formula
C10H13N5O4S
CAS number
30516-87-1
IUPAC name
[(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl] 4-methylbenzenesulfonate
State
State

Zidovudine at room temperature is typically in a solid state, appearing as a crystalline powder.

Melting point (Celsius)
123.00
Melting point (Kelvin)
396.00
Boiling point (Celsius)
405.00
Boiling point (Kelvin)
678.00
General information
Molecular weight
267.24g/mol
Molar mass
267.2440g/mol
Density
1.6400g/cm3
Appearence

Zidovudine generally appears as a white to beige, odorless, crystalline powder. It is slightly soluble in water, sparingly soluble in methanol, and practically insoluble in chloroform and ethyl acetate.

Comment on solubility

Solubility of [(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl] 4-methylbenzenesulfonate

The solubility of compounds such as [(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl] 4-methylbenzenesulfonate can be influenced by various factors including its molecular structure and the presence of functional groups. Analyzing the solubility characteristics of this compound can yield interesting insights:

  • Polarity: The compound features multiple hydroxyl groups and a sulfonate group, which typically enhances solubility in polar solvents such as water.
  • Hydrogen Bonding: The presence of hydroxyl groups allows for increased hydrogen bonding potential, contributing to better solubility in aqueous conditions.
  • Hydrophobic Interactions: The aromatic sulfonate group may introduce hydrophobic characteristics, which can affect solubility in non-polar solvents.
  • pH Dependency: As a sulfonate, the solubility of the compound may vary with pH, as it can exist in different ionization states influencing its solubility profile.

In summary, the solubility of this compound can be described as likely moderate to high in polar solvents, largely due to its functional groups promoting interaction with water molecules. Understanding these solubility characteristics is crucial for various applications, including drug formulation and biochemical interactions.

Interesting facts

Interesting Facts about [(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl] 4-methylbenzenesulfonate

This compound is a fascinating example of modern medicinal chemistry, showcasing the vibrant connectivity between organic synthesis and pharmaceutical development. The structure of this molecule is particularly intriguing due to its incorporation of various functional groups that can significantly influence its biological activity.

Chemical Significance

  • Diverse Functional Groups: The compound features a tetrahydrofuran ring, hydroxyl groups, and a pyrimidine derivative, suggesting potential interactions with biological molecules.
  • Potential Therapeutic Uses: The presence of a pyrimidine ring hints at potential applications in nucleic acid synthesis or as an antibiotic.
  • Solubility Variability: Its sulfonate group can enhance solubility in aqueous environments, making it an attractive candidate for drug formulation.

Biological Implications

Compounds like this often serve as a backbone for developing new medicinal agents, potentially targeting diseases associated with cellular processes. The study of such compounds helps in elucidating pathways that could be manipulated for therapeutic purposes.

Why Study This Compound?

Understanding the intricate details of this compound contributes to the broader field of drug design and assists in:

  • Identifying structure-activity relationships that inform future designs.
  • Establishing a database of compounds that reflect biological efficacy.
  • Enhancing knowledge of how modifications to the molecular structure can elicit specific pharmacological responses.

In conclusion, this compound not only embodies the complexity of organic chemistry but also serves as a beacon for future research in drug discovery and development. As the field advances, the insights gained from analyzing such compounds will be invaluable in tackling various health challenges.

Synonyms
6206-10-6
URIDINE, 2'-P-TOLUENESULFONATE
DTXSID00211114
DTXCID00133605
[(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] 4-methylbenzenesulfonate
AKOS030489704
[(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]4-methylbenzenesulfonate