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Fluorouracil prodrug

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Identification
Molecular formula
C23H28FNO6
CAS number
NA
IUPAC name
methyl 3-[2-[[2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]propanoylamino]-5-fluoro-4-oxo-pentanoate
State
State

At room temperature, it is in a solid state, forming a crystalline powder.

Melting point (Celsius)
217.00
Melting point (Kelvin)
490.15
Boiling point (Celsius)
489.70
Boiling point (Kelvin)
762.85
General information
Molecular weight
432.45g/mol
Molar mass
432.4520g/mol
Density
1.2500g/cm3
Appearence

Methyl 3-[2-[[2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]propanoylamino]-5-fluoro-4-oxo-pentanoate is typically a white crystalline powder. Appearance can vary slightly based on purity and preparation methods.

Comment on solubility

Solubility of Methyl 3-[2-[[2-(Benzyloxycarbonylamino)-3-methyl-butanoyl]amino]propanoylamino]-5-fluoro-4-oxo-pentanoate

The solubility of methyl 3-[2-[[2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]propanoylamino]-5-fluoro-4-oxo-pentanoate (C23H28FNO6) is an intriguing aspect to consider. This compound contains several functional groups that may influence its interaction with solvents.

Factors Affecting Solubility:

  • Polarity: The presence of polar functional groups can enhance solubility in polar solvents like water.
  • Hydrophobic Regions: The benzyloxycarbonyl groups may introduce hydrophobic characteristics affecting solubility in organic solvents.
  • Hydrogen Bonding: Amino and carbonyl groups can participate in hydrogen bonding, potentially improving solubility in suitable solvents.

In general, the solubility can be described as follows:

  • Soluble in: Organic solvents, such as DMSO and methanol.
  • Slightly soluble or insoluble in: Water at room temperature due to hydrophobic characteristics.

As with many compounds, it is essential to determine solubility under specific conditions, because "solubility is a dynamic equilibrium." Changes in temperature, pH, and concentration can significantly influence the solubility behavior. Thus, further experimental data is often required to fully characterize the solubility of this complex molecule.

Interesting facts

Interesting Facts about Methyl 3-[2-[[2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]propanoylamino]-5-fluoro-4-oxo-pentanoate

Methyl 3-[2-[[2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]propanoylamino]-5-fluoro-4-oxo-pentanoate is a fascinating compound that belongs to the class of amino acids and peptides. Here are some remarkable aspects worth noting:

  • Complex Structure: This compound features a complex multi-functional structure, showcasing the intricate interplay of amine and keto groups. Its diverse functionalities make it an interesting subject for study in pharmaceutical chemistry.
  • Fluorine Incorporation: The presence of a fluorine atom in its structure is particularly intriguing. Fluorinated compounds often exhibit enhanced biological activity and stability, making them valuable in drug design. Fluorine can also influence the lipophilicity of the compound, impacting its absorption and distribution in biological systems.
  • Potential Therapeutic Applications: Compounds similar to this one are often evaluated for their efficacy in treating various diseases, including cancers and metabolic disorders, primarily due to their ability to mimic natural substrates and inhibit specific enzymes.
  • Peptide Synthesis: The synthesis of this compound could involve advanced peptide coupling techniques. Understanding these methods is crucial for scientists focusing on the development of peptide-based therapeutics.
  • Usage in Research: Researchers often use this compound as a reference standard or starting material to explore and develop new compounds with improved therapeutic properties. It serves as a model for studying the structure-activity relationship (SAR).

In conclusion, methyl 3-[2-[[2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]propanoylamino]-5-fluoro-4-oxo-pentanoate provides a gateway into the world of medicinal chemistry, challenging chemists to explore its potential and push the boundaries of what is achievable in drug development.

Synonyms
634911-81-2
N-[(Phenylmethoxy)carbonyl]-L-valyl-N-[(1S)-3-fluoro-1-(2-methoxy-2-oxoethyl)-2-oxopropyl]-L-alaninamide
Benzyloxycarbonyl-Val-Ala-Asp(OMe)-fluoromethylketone
MFCD02684037
HMS3652F16
BCP07127
AKOS032960280
DA-43423
SY068305
Methyl (S)-3-[(S)-2-[(S)-2-(Cbz-amino)-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoate