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ChemicalBook--->CAS DataBase List--->69123-90-6

69123-90-6

69123-90-6 Structure

69123-90-6 Structure
IdentificationBack Directory
[Name]

4-Amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one
[CAS]

69123-90-6
[Synonyms]

FIAC
FOAC
NSC382097
NSC 382097
NSC -82097
Fiacitabine
NSC-382097;FIAC
Fiacitabine (NSC-382097
NSC 382097; FIAC; FOAC;NSC382097; NSC -82097
5-Iodo-2’-deoxy-2’-fluoro-β-D-arabinocytidine
5-Iodo-2'-deoxy-2'-fluoro-beta-D-arabinocytidine
1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodocytosine
4-aMino-1-(2-deoxy-2-fluoro-b-D-arabinofuranosyl)-5-iodo-
5-Iodo-2’-deoxy-2’-fluoro-beta-D-arabinocytidine, Fiacitabine
2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodo-
4-Amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one
[Molecular Formula]

C9H11FIN3O4
[MDL Number]

MFCD00868897
[MOL File]

69123-90-6.mol
[Molecular Weight]

371.1
Chemical PropertiesBack Directory
[Boiling point ]

524.6±60.0 °C(Predicted)
[density ]

2.44±0.1 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

DMSO: ≥ 37 mg/mL (99.70 mM)
[form ]

Powder
[pka]

12.84±0.70(Predicted)
[color ]

White to off-white
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Cytosine-->2-deoxy-2-fluoro-3-phenylpropanoyl-α-D-arabinofuranose
Hazard InformationBack Directory
[Description]

Fiacitabine is a pyrimidine nucleoside analog with activity against various herpesviruses. It is converted to its triphosphate form in vivo and inhibits viral DNA polymerase. It has been used in trials studying the treatment of HIV Infections and Cytomegalovirus Infections.
[Uses]

Antiviral.
[Preparation]

The preparation method for Fecitabine involves using 2-deoxy-2-fluoro-tribenzoyl-α-D-arabinofuranose as the raw material. The arabinofuranose is brominated with the hydrobromic acetic acid solution under normal room temperature conditions to obtain 2-deoxy-2-fluoro-tribenzoyl-α-D-brominated arabinofuranose. Next, cytosine is used as the raw material for iodination and is Bz-protected to obtain -(5-Iodo-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide, which serves as the final intermediate. After the reaction, deprotection is carried out to obtain Fecitabine with a total yield as high as 43%.?
[storage]

Store at -20°C
[Mode of action]

Fiacitabine is an antimicrobial agent that inhibits microbial growth by binding to the ribosomal 30S subunit and blocking protein synthesis. It is a prodrug that is converted to 5-fluorocytosine (5FC) in the liver, where it inhibits the activity of the enzyme dihydropyrimidine dehydrogenase, thereby interfering with DNA replication.
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