78636-53-0

Basic information

• Product Name: 2'-fluoro-5-methylarabino-furanosylcytosine
• Synonyms: 2'-fluoro-5-methylarabino-furanosylcytosine;2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-;2'-Deoxy-2'-fluoro-5-Methyl-beta-D-arabinocytidine;2'-Deoxy-2'-fluoro-5-methyl-araobinocytidine;4-Amino-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2(1H)-pyrimidinone
• CAS NO: 78636-53-0
• Molecular Formula: C₁₀H₁₄FN₃O₄
• Molecular Weight: 259.2343
• Mol File: 78636-53-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 495.4 ºC at 760 mmHg
• Flash Point: 253.4 ºC
• Appearance: /
• Density: 1.73 g/cm³
• Vapor Pressure: 6.81E-12mmHg at 25°C
• Refractive Index: 1.674
• CAS DataBase Reference: 2'-fluoro-5-methylarabino-furanosylcytosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-fluoro-5-methylarabino-furanosylcytosine(78636-53-0)
• EPA Substance Registry System: 2'-fluoro-5-methylarabino-furanosylcytosine(78636-53-0)

Safety Data

• Hazardous Substances Data: 78636-53-0(Hazardous Substances Data)

Usage

General Description

2'-fluoro-5-methylarabino-furanosylcytosine, also known as FMAU, is a synthetic nucleoside analog that has shown potential as an antiviral and antitumor drug. It is a fluorinated derivative of cytosine, a natural component of DNA and RNA, and the addition of a fluoro and methyl group to the sugar moiety of the cytosine molecule enhances its stability and inhibitory properties. FMAU has been studied for its ability to inhibit the replication of certain viruses, including herpes simplex virus and hepatitis B virus, as well as for its potential as a cancer treatment, particularly for liver cancer. Research has also suggested that FMAU may have less toxicity and better selectivity compared to other nucleoside analogs, making it a promising candidate for further drug development.

InChI:InChI=1/C10H14FN3O4/c1-4-2-14(10(17)13-8(4)12)9-6(11)7(16)5(3-15)18-9/h2,5-7,9,15-16H,3H2,1H3,(H2,12,13,17)/t5-,6+,7-,9+/m1/s1

Upstream product

• 83966-95-4 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methylcytosine 
• 554-01-8 5-methylcytosin 
• 56632-81-6 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide 
• 84025-00-3 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose 

Downstream Products

• 69256-17-3 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine 

Relevant articles and documents

Probing Synergistic Effects of DNA Methylation and 2′-β-Fluorination on i-Motif Stability

The possible role of DNA i-motif structures in telomere biology and in the transcriptional regulation of oncogene promoter regions is supported by several recent studies. Herein we investigate the effect of four cytidine nucleosides (and combinations thereof) on i-motif structure and stability, namely 2′-deoxycytidine (dC), 2′-deoxy-5-methyl-cytidine (5-Me-dC), 2′-deoxy-2′-fluoro-arabinocytidine (2′F-araC), and 2′-deoxy-2′-fluoro-5-methyl-arabinocytidine (5-Me-2′F-araC). The base pair 5-Me-2′F-araC:2′F-araC produced i-motifs with a pH1/2 (“pKa”) value that closely matches physiological pH (7.34±0.3). NMR analysis of the most stable telomeric sequence (HJ-2) at pH 7.0 indicated that the structure is stabilized by hybrid 5-Me-dC:2′F-araC hemiprotonated base pairs and therefore highlights the significance of the interplay between base and sugar modifications on the stability of i-motif structures.

5-Substituted 1-(2'-Deoxy-2'-substituted-β-D-arabinofuranosyl)pyrimidine nucleosides

Pyrimidine nucleosides exhibiting anti-viral and anti-tumor effects have the formula STR1 wherein A is OR3, SR3, NR3 R4 or NHacyl wherein R3 and R4 are the same or different and are hydroge