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Identification
Molecular formula
C12H15F2N5O3
CAS number
142217-69-4
IUPAC name
4-amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
State
State

This compound is typically solid at room temperature.

Melting point (Celsius)
220.90
Melting point (Kelvin)
494.05
Boiling point (Celsius)
266.00
Boiling point (Kelvin)
539.15
General information
Molecular weight
276.28g/mol
Molar mass
276.2720g/mol
Density
1.9500g/cm3
Appearence

The compound appears as a white to off-white crystalline powder.

Comment on solubility

Solubility of 4-amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one

The solubility of the compound 4-amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one (C12H15F2N5O3) is an important characteristic that influences its applications in various chemical processes. Here are some key aspects to consider:

  • Polar Functional Groups: The presence of multiple hydroxyl (-OH) groups can enhance solubility in polar solvents, particularly water.
  • Fluorine Atoms: The difluoro moiety may affect solubility differently compared to other common functional groups, as fluorinated compounds often demonstrate unique solvation behaviors.
  • Structural Rigidity: The tetrahydrofuran ring introduces a level of structural complexity that may impact molecular interactions with solvents.
  • Hydrogen Bonding: The potential for hydrogen bonding due to both the amino and hydroxyl groups may significantly increase solubility in aqueous environments.

It is also noteworthy that solubility can be influenced by several external factors, such as:

  1. Temperature: Increased temperatures typically enhance solubility for many compounds.
  2. pH Levels: The ionization of various functional groups may vary with pH, thereby affecting solubility in different environments.
  3. Presence of Co-solvents: Adding co-solvents can also affect solubility, particularly in organic chemistry applications.

In summary, the solubility of 4-amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one is influenced by its complex structure and the presence of both polar and nonpolar characteristics, making it a fascinating compound to study in both theoretical and practical contexts.

Interesting facts

Interesting Facts About 4-amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one

This intriguing compound is a member of the pyrimidine family and presents a unique blend of properties that make it notable in the field of medicinal chemistry. Here are some striking points about this compound:

  • Therapeutic Potential: Compounds like this one are often explored for their potential use in pharmaceuticals, especially in antiviral and antitumor therapies, due to their ability to interfere with nucleic acid synthesis.
  • Structural Complexity: The structure features a tetrahydrofuran ring, which is significant in terms of stability and reactivity, enhancing its bioavailability compared to simpler compounds.
  • Difluorination: The incorporation of difluoromethyl groups is of particular interest, as fluorine can modulate the pharmacokinetics of the compound, making it more effective in biological systems.
  • Hydroxymethyl Group: The presence of a hydroxymethyl substituent can participate in hydrogen bonding, influencing the compound's interactions with biological targets.
  • Research Applications: Scientists are keen to investigate its mechanics through techniques like X-ray crystallography and NMR spectroscopy, providing insights into its conformation and activity.

As noted by one researcher, "The unique architecture of this compound offers a remarkable glimpse into how small changes in structure can significantly impact biological activity." With ongoing research, this compound may reveal new pathways for drug development and contribute to innovative therapeutic solutions.

Synonyms
3'-Epi Gemcitabine (Gemcitabine Impurity)
103882-85-5
4-amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-2-oxolanyl]-2-pyrimidinone
4-amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
701937-51-1
3'-EPI GEMCITABINE
4-amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
Gemctitabine
4-amino-1-(2-deoxy-2,2-difluoropentofuranosyl)pyrimidin-2(1H)-one
MFCD00869720
Neuro_000239
SCHEMBL94960
CHEMBL264883
CHEBI:93766
DTXSID00861138
SDUQYLNIPVEERB-UHFFFAOYSA-N
HMS3655E04
NSC750927
STL301148
ZINC00006532
AKOS015892326
NE22706
NSC-750927
SB17337
LS-13624
NCI60_004898
SY097030
DB-014817
EN300-270181
F14951
AB01273934-01
Q27165457
4-amino-1-((4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
4-Amino-1-(deoxy-2,2-difluoro-D-threo-pentofuranosyl)-2(1H)-pyrimidinone;Gemcitabine impurity
4-amino-1-[(2S,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one