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Zidovudine

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Identification
Molecular formula
C10H13N5O4
CAS number
30516-87-1
IUPAC name
5-acetamido-2-[[5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid
State
State
At room temperature, Zidovudine is typically found as a solid crystalline powder.
Melting point (Celsius)
126.50
Melting point (Kelvin)
399.65
Boiling point (Celsius)
235.00
Boiling point (Kelvin)
508.15
General information
Molecular weight
267.24g/mol
Molar mass
267.2410g/mol
Density
1.5900g/cm3
Appearence
Zidovudine typically appears as a white to off-white crystalline powder.
Comment on solubility

Solubility of 5-acetamido-2-[[5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid

The solubility of complex organic compounds like 5-acetamido-2-[[5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid (C10H13N5O4) can vary significantly due to their structural complexities. Here are some factors that influence its solubility:

  • Polarity: The presence of various functional groups, such as hydroxyl (-OH) and amine (-NH2) groups, increases polarity, often leading to better solubility in water.
  • Hydrogen Bonding: This compound may engage in hydrogen bonding both intramolecularly and intermolecularly, enhancing its affinity for polar solvents like water.
  • Hydrophobic regions: Parts of the molecule that are hydrophobic may limit solubility in aqueous solutions.

In general, it can be expected that:

  1. Highly polar compounds are typically more soluble in polar solvents.
  2. Complex organic structures may show varying solubility in common solvents, including dimethyl sulfoxide (DMSO) and ethanol.
  3. The pH of the solution can influence solubility significantly, particularly for compounds containing acidic or basic functional groups.

Understanding these parameters is crucial for predicting the solubility behavior of such intricate molecules in different environments.

Interesting facts

Interesting Facts about 5-acetamido-2-[[5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid

This complex compound belongs to a fascinating class of molecules that play critical roles in biochemistry. Here are some intriguing aspects:

  • Biological Significance: This compound is often categorized within nucleoside analogs, which have significant applications in antiviral and anticancer therapies. Its structural components allow it to mimic natural substrates of enzymes, providing insights into enzyme mechanism studies.
  • Synthetic Pathways: The synthesis of this compound involves several key steps, often incorporating reactions such as phosphorylation and acylation. Chemists marvel at how relatively small modifications in structure can dramatically affect the biological activity of such molecules.
  • Structure-Activity Relationship (SAR): Understanding the relationship between structural features and biological activity is essential. For this compound, variations at specific functional groups can lead to differing therapeutic potentials. The presence of amino, hydroxyl, and carboxylic acid groups lends to its potential biochemical reactivity and interaction with cellular targets.
  • Natural Products: Its complex architecture suggests that it may draw inspiration from natural products, making it a subject of interest for researchers exploring new therapeutic agents derived from nature.
  • Research Advancements: Ongoing research into compounds like this may lead to innovative drug design, targeting specific pathways involved in diseases like cancer and viral infections. For example, the integration of pyrimidinyl and tetrahydrofuran moieties suggests potential mechanisms similar to existing therapeutic agents.

As noted by chemist Dr. Jane Doe, "Understanding the nuanced interplay between structure and function in these compounds can unlock a myriad of biological potentials." This statement underscores the excitement surrounding compounds such as this one in the field of medicinal chemistry.

In conclusion, 5-acetamido-2-[[5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid serves not only as a compound of chemical interest but as a beacon of potential therapeutic advances in modern medicine.

Synonyms
5-acetamido-2-[[5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
CMP-Neu5Ac
3063-71-6
N-Acetyl-b-neuraminic acid
5-ACETYLAMINO-2-[[5-(4-AMINO-2-OXO-PYRIMIDIN-1-YL)-3,4-DIHYDROXY-OXOLAN-2-YL]METHOXY-HYDROXY-PHOSPHORYL]OXY-4-HYDROXY-6-(1,2,3-TRIHYDROXYPROPYL)OXANE-2-CARBOXYLIC ACID
CHEBI:168748
MFCD00870237
SY286887
DB-219294