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Cytosine arabinoside

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Identification
Molecular formula
C9H13N3O5
CAS number
147-94-4
IUPAC name
4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
State
State

At room temperature, cytosine arabinoside is in a solid state, typically in the form of a crystalline powder.

Melting point (Celsius)
212.00
Melting point (Kelvin)
485.15
Boiling point (Celsius)
325.00
Boiling point (Kelvin)
598.15
General information
Molecular weight
243.22g/mol
Molar mass
243.2190g/mol
Density
1.5400g/cm3
Appearence

Cytosine arabinoside appears as a white to off-white crystalline powder.

Comment on solubility

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

The solubility of 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one in various solvents is an essential property that influences its application and effectiveness in a range of chemical and biological contexts. This compound, synthesized from a complex framework, exhibits unique solubility characteristics due to its functional groups.

Key Points on Solubility:

  • Aqueous Solubility: The presence of hydroxyl groups likely enhances the molecule's ability to interact with water, suggesting a higher solubility in aqueous solutions.
  • Organic Solvents: Despite favorable solubility in water, the compound's solubility in organic solvents may vary, potentially being lower due to the steric hindrance from its complex structure.
  • pH Influence: The solubility may also be affected by the pH of the solution, particularly due to the amino group which can accept or donate protons, thus altering solubility at different pH levels.
  • Utilization in Formulations: Understanding solubility is crucial for its optimization in pharmaceutical formulations, as it can enhance bioavailability and therapeutic effectiveness.

In summary, the intricate balance of hydrophilicity driven by hydroxyl groups and potential steric factors suggests that 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one has promising solubility properties, especially in aqueous media. Further qualitative studies will provide a deeper insight into the specific solubility behaviors across different solvent systems.

Interesting facts

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

This compound is a fascinating example of a pyrimidine derivative that incorporates a complex carbohydrate moiety. Its unique structure and presence of multiple functional groups make it of significant interest in the field of medicinal chemistry.

  • Biological Activity: Compounds similar to this one often exhibit properties that can be beneficial in treating various diseases, especially viral infections.
  • Structural Diversity: The inclusion of a tetrahydrofuran ring and hydroxymethyl groups adds to the compound's structural diversity, enhancing its potential interactions with biological targets.
  • Potential Applications: This compound may be explored for its role in drug design, particularly in the development of antiviral or anticancer agents, due to its structural motifs that resemble those found in nucleosides.
  • Chirality and Stereochemistry: The specific chiral centers in the compound (like 2R, 4S, 5R) are critical for the biological activity, as even slight changes can dramatically affect how a drug interacts with its target.

As quoted by prominent chemists, "the devil is in the details" when it comes to drug design; understanding the stereochemistry and functional groups of compounds like this one can provide insights into their mechanisms of action and therapeutic potential. The study of such compounds is not just a quest for knowledge but could lead to breakthroughs in treatment methodologies.

In summary, 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one holds a promising position in the realm of chemical research, especially within the fields of biochemistry and pharmacology.

Synonyms
2'-deoxycytidine
deoxycytidine
951-77-9
CYTIDINE, 2'-DEOXY-
Deoxyribose cytidine
Cytosine deoxyriboside
4-Amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
Desoxycytidin [German]
Desoxycytidin
Doxecitine
d-cytidine
Cytosine, deoxyribonucleoside
1beta-2'-Deoxyribofuranosylcytosine, d-
EINECS 213-454-1
4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
BRN 0087567
CHEBI:15698
1-(2-Deoxy-beta-D-ribofuranosyl)cytosine
DOXECITINE [INN]
0W860991D6
DTXSID70883620
4-25-00-03662 (Beilstein Handbook Reference)
1-(2-deoxy-.beta.-d-ribofuranosyl)cytosine
4-Amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone
4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
4-amino-1-(2-deoxy-.beta.-d-erythro-pentofuranosyl)-2(1h)-pyrimidinone
4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one
Deoxyriboside, Cytosine
Deoxyribonucleoside, Cytosine
2'deoxycytidine
4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2-dihydropyrimidin-2-one
4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrimidin-2-one
Cytidine, 2'deoxy
DEOXYCYTIDINE [INCI]
DTXCID901023131
1beta2'Deoxyribofuranosylcytosine, d
213-454-1
dCYD
207121-53-7
DC
MFCD00006547
Desoxycytidine
56905-41-0
Deoxycytidine;Cytosine deoxyriboside;Deoxyribose cytidine
2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-
2'-deoxy-cytidine
2 inverted exclamation marka-Deoxycytidine
deoxy-Cytidine
2-Deoxycytidine
2' Deoxycytidine
2-deoxy-Cytidine
UNII-0W860991D6
Cytidine, 2'-deoxy-, labeled with tritium
Doxecitine (USAN/INN)
DOXECITINE [USAN]
SCHEMBL23178
2'-dC
CHEMBL66115
MT1621 (dC)
HY-D0184
BDBM50367094
HG1097
2'-Deoxycytidine, >=99% (HPLC)
AKOS015896791
AC-8210
DB02594
1-(2-Deoxy-b-D-ribofuranosyl)cytosine
4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
NCGC00142493-01
AS-14313
BP-58643
CS-0010105
D3583
MT-1621 COMPONENT 2'-DEOXYCYTIDINE
NS00120718
1-(2-Deoxy-beta-delta-ribofuranosyl)cytosine
C00881
D12465
EN300-6477283
Q422504
1-(2-deoxy-beta-D-erythro-pentofuranosyl)-Cytosine
BRD-K91822704-001-01-9
BRD-K91822704-003-07-2
1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-Cytosine
Z3072884208
4-Amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone
4-Amino-1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-2(1H)-pyrimidinone