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Tegafur

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Identification
Molecular formula
C8H9FN2O3
CAS number
17902-23-7
IUPAC name
1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione
State
State

At room temperature, Tegafur is in a solid state. It is stable and typically stored in its solid form as a powder.

Melting point (Celsius)
166.00
Melting point (Kelvin)
439.15
Boiling point (Celsius)
287.00
Boiling point (Kelvin)
560.15
General information
Molecular weight
214.17g/mol
Molar mass
214.1960g/mol
Density
1.4710g/cm3
Appearence

Tegafur typically appears as a white to off-white crystalline powder. It is odorless and has a bitter taste. It is often provided in a finely milled form for pharmaceutical compounding.

Comment on solubility

Solubility of 1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione

The solubility of 1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione can be influenced by several key factors. Understanding its solubility behavior is essential for its applications in pharmaceuticals and material science. Here are some considerations:

  • Polarity: The presence of hydroxymethyl groups generally increases the polarity of the compound, which can enhance its solubility in polar solvents, such as water.
  • Hydrogen Bonding: This compound can form hydrogen bonds due to hydroxyl groups, further aiding its solubility in polar media.
  • Temperature Effects: Solubility may increase with temperature; thus, experiments at various temperatures can help determine optimal solubility conditions.
  • pH Dependence: Solubility can vary with pH levels, likely affecting ionization states and solvation dynamics.

In summary, while 1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione demonstrates potential for good solubility in polar environments due to its functional groups, precise measurements and adjustments may be required based on application needs. As always, when evaluating solubility, consider the role of solvent choice, temperature, and pH for the most accurate insights.

Interesting facts

Interesting Facts about 1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione

The compound 1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione is a fascinating example of modern organic chemistry, showcasing the beauty of chiral molecules and their applications. Here are some engaging aspects of this compound:

  • Chirality: The presence of multiple chiral centers in the tetrahydrofuran moiety adds to the complexity and uniqueness of this compound. Chirality in compounds often leads to different biological activities, making it crucial in drug development.
  • Fluorine Substitution: The incorporation of a fluorine atom can significantly enhance the pharmacological properties of organic compounds. Fluorine’s electronegativity can improve the metabolic stability and binding efficiency of the compound, often leading to enhanced therapeutic effects.
  • Biological Relevance: Compounds like this pyrimidine derivative are of interest in medicinal chemistry. Pyrimidine derivatives are known to exhibit diverse biological activities and can be utilized in the design of new pharmaceuticals.
  • Versatile Applications: Beyond medicinal applications, this compound may also serve as a building block for various chemical intermediates owing to its functional groups, paving the way for further synthetic innovations.
  • Structure-Activity Relationship (SAR): Understanding how structural modifications affect biological activity is a key focus in drug design. The unique structure of this compound invites extensive SAR studies to uncover its full potential.

In conclusion, the compound 1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione exemplifies the intersection of organic chemistry and medicinal research. Its intricate structure, coupled with the strategic incorporation of fluorine and hydroxymethyl groups, underscores its potential importance in pharmaceutical applications. As we continue to explore its properties and functionalities, this compound may very well contribute to the next generation of therapeutic agents.

Synonyms
Alovudine
25526-93-6
3'-DEOXY-3'-FLUOROTHYMIDINE
3'-Fluoro-3'-deoxythymidine
FddT
CL 184824
Alovudina
MIV-310
PG53R0DWDQ
3'-Fluorothymidine
NSC-140025
DTXSID4046579
CL-184824
CL 184,824
MIV310
CL-184,824
DTXCID2026579
(18)FLT cpd
1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
alovudinum
1-((2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl)-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
3'-fluoro-2',3'-dideoxythymidine
RefChem:554979
3'-(F-18)fluoro-3'-deoxythymidine
1-(3'-fluoro-3'-deoxy-beta-D-erythropentofuranosyl)thymine
Thymidine, 3'-deoxy-3'-fluoro-
FddThD
3'F-TdR
1-((2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
MFCD00056058
1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
3'-Fluorodeoxythymidine
CHEMBL105318
3'-Deoxy-3'-fluoro Thymidine
FLT
1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione
3'-FddT
Alovudine [USAN:INN]
CAS-25526-93-6
3'-FLT
DRG-0097
UNII-PG53R0DWDQ
NSC 140025
BRN 0754299
Alovudine?
NSC140025
NCGC00166256-01
3'-Deoxy-3'-18F fluorothymidine
1-(3'-Deoxy-3'-fluoro-beta-D-pentofuranosyl)thymine
ALOVUDINE [INN]
Alovudine (USAN/INN)
ALOVUDINE [USAN]
3-Deoxy-3-fluorothymidine
ALOVUDINE [WHO-DD]
SCHEMBL133722
3'-deoxy-3'-fluoro-thymidine
orb1302656
SCHEMBL10379566
CHEBI:177762
3'-Deoxy-3'-fluoro-L-Thymidine
HY-B1516
Tox21_112376
BDBM50132287
s6848
3'-Deoxy-3'-fluorothymidine, 97%
AKOS015917785
Tox21_112376_1
DB06198
ND02399
3''-Fluoro-2'',3''-dideoxythymidine
NCGC00166256-02
3'-Fluoro-3'-deoxythymidine (Alovudine)
AS-60404
SY014685
CS-0013305
NS00068737
D02830
526D936
F600867
Q4734671
1-(3-fluoro-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine
1-[(2R,4S,5R)-4-luoro-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
3 inverted exclamation mark -Deoxy-3 inverted exclamation mark -fluorothymidine
1-((2R,5R)-4-Fluoro-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
1-(3-Fluoro-2,3-dideoxy-?-D-ribofuranosyl)thymine;1-(3'-Deoxy-3'-fluoro--D-pentofuranosyl)thymine
128075-91-2
2543835-70-5
25515-31-5