69123-90-6

Basic information

• Product Name: 4-Amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one
• Synonyms: Fiacitabine;4-Amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one;2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodo-;4-aMino-1-(2-deoxy-2-fluoro-b-D-arabinofuranosyl)-5-iodo-;FIAC;FOAC;NSC 382097;NSC382097
• CAS NO: 69123-90-6
• Molecular Formula: C₉H₁₁FIN₃O₄
• Molecular Weight: 371.1
• Mol File: 69123-90-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 524.6 °C at 760 mmHg
• Flash Point: 271.1 °C
• Appearance: /
• Density: 2.44 g/cm³
• Vapor Pressure: 3.37E-13mmHg at 25°C
• Refractive Index: 1.791
• PKA: 12.84±0.70(Predicted)
• CAS DataBase Reference: 4-Amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one(69123-90-6)
• EPA Substance Registry System: 4-Amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one(69123-90-6)

Safety Data

• Hazardous Substances Data: 69123-90-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 69123-90-6 differently. You can refer to the following data:
1. Antiviral.
2. Fiacitabine is an antiviral compound and a selective inhibitior of DNA replication of herpes simplex virus(HSV).

InChI:InChI=1/C9H11FIN3O4/c10-5-6(16)4(2-15)18-8(5)14-1-3(11)7(12)13-9(14)17/h1,4-6,8,15-16H,2H2,(H2,12,13,17)

Upstream product

• 83967-00-4 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodocytosine 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 
• 97614-44-3 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide 
• 1382358-19-1 1-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-5-iodocytosine 
• 84025-00-3 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose 
• 56632-81-6 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide 

Downstream Products

• 85714-55-2 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethynylcytosine 
• 119555-47-4 1-(2,3-Dideoxy-2-fluoro-β-D-arabinofuranosyl)-cytosine 
• 128115-03-7 1-<2-deoxy-2-fluoro-3-O-<(imidazol-1-yl)thiocarbonyl>-5-O-trityl-β-D-arabinofuranosyl)-5-iodocytosine 
• 128115-06-0 1-<5-O-benzoyl-2-deoxy-2-fluoro-3-O-<(imidazol-1-yl)thiocarbonyl>-β-D-arabinofuranosyl>-N⁴-benzoylcytosine 
• 128115-05-9 4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one 
• 128115-04-8 1-(2,3-dideoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)cytosine 
• 121353-94-4 1-(5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-N⁴-benzoylcytosine 
• 128115-07-1 1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl-N⁴-benzoylcytosine 
• 56632-83-8 1-(2-fluoro-2-deoxy-β-D-arabinofuranosyl)cytosine 
• 95740-12-8 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5(E)-<2-(ethoxycarbonyl)vinyl>cytosine 
• 105281-00-3 Toluene-4-sulfonic acid (2R,3R,4S,5R)-5-(4-amino-5-iodo-2-oxo-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 
• 128115-02-6 1-(2-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)-5-iodocytosine 
• 105281-13-8 1-(5-amino-2,5-dideoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodocytosine 
• 105281-15-0 1-(3-O-acetyl-2-deoxy-2-fluoro-5-O-tosyl-β-D-arabinofuranosyl)-5-iodocytosine 

Relevant articles and documents

Synthesis of DNA oligos containing 2′-deoxy-2′-fluoro-d- arabinofuranosyl-5-carboxylcytosine as hTDG inhibitor

As an important step of the active demethylation of 5-methylcytosine (5mC), human thymine DNA glycosylase (hTDG) efficiently excises 5-carboxylcytosine (5caC) from double-stranded DNA (dsDNA). Here, we present synthesis of DNA oligos containing a 2′-deoxy-2′-fluoro-d-arabinofuranosyl-5- carboxylcytidine (F-5caC) modification that act as hTDG inhibitors. The glycosylase activity assay showed that F-5caC oligos were resistant to excision by the hTDG catalytic domain (hTDGcat, residues 111-308) and they could inhibit the excision of DNA oligos containing 5caC. The electrophoretic mobility shift assay confirmed that DNA oligos containing F-5caC could bind well with unmodified hTDGcat to form a stable complex, which makes it possible to obtain the crystal structure of the complex to reveal details on how hTDGcat recognizes the DNA substrate.

Nucleosides. 123. Synthesis of Antiviral Nucleosides: 5-Substituted 1-(2-Deoxy-2-halogeno-β-D-arabinofuranosyl)cytosines and -uracils. Some Structure-Activity Relationships

The syntheses of several 2'-halogeno-5-substituted-arabinofuranosylcytosines and -uracils are described, and relationships of structure to anti herpes virus activity in vitro were examined.Those arabinonucleosides containing the 2'-fluoro function exhibit