80791-93-1

Basic information

• Product Name: 2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE
• Synonyms: 2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE;4-amino-1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one;4-amino-1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2-dihydropyrimidin-2-one;4-AMINO-1-((3R,4R,5R)-3-FLUORO-4-HYDROXY-5-(HYDROXYMETHYL)TETRAHYDROFURAN-2-YL)-5-IODOPYRIMIDIN-2(1H)-ONE
• CAS NO: 80791-93-1
• Molecular Formula: C₉H₁₁FIN₃O₄
• Molecular Weight: 371.101
• Product Categories: Anti-HCV;Antivira
• Mol File: 80791-93-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE(80791-93-1)
• EPA Substance Registry System: 2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE(80791-93-1)

Safety Data

• Hazardous Substances Data: 80791-93-1(Hazardous Substances Data)

Usage

Description

2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE is a modified nucleoside that plays a significant role in the synthesis of cytidine-5-carboxamide modified nucleotides. It is characterized by the presence of a fluorine atom at the 2'' position and an iodine atom at the 5-position, which imparts unique properties to the molecule. 2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE is of interest in the field of molecular biology and drug development due to its potential applications in various areas.

Uses

Used in Pharmaceutical Industry:
2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE is used as a key intermediate in the synthesis of cytidine-5-carboxamide modified nucleotides for the development of novel antiviral and anticancer drugs. The unique structural features of this compound allow for the design of drugs with improved pharmacological properties, such as enhanced stability, selectivity, and potency.
Used in Molecular Biology Research:
In molecular biology research, 2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE is used as a building block for the preparation of modified nucleotides that can be incorporated into DNA. These modified nucleotides can be used to study various biological processes, such as DNA replication, repair, and transcription, as well as to develop new techniques for genetic engineering and gene therapy.
Used in Diagnostic Applications:
2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE can also be used in the development of diagnostic tools, such as fluorescently labeled probes for DNA sequencing, detection of specific genetic sequences, and monitoring of gene expression. The presence of the iodine atom in the molecule allows for the attachment of reporter groups, enabling the detection and quantification of target DNA sequences in various biological samples.
Overall, 2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE is a versatile compound with a wide range of applications in the pharmaceutical, molecular biology, and diagnostic industries. Its unique structural features make it an attractive candidate for the development of novel therapeutic agents, research tools, and diagnostic technologies.

Upstream product

• 10212-20-1 2'-deoxy-2'-fluorocytidine 
• 31698-14-3 cyclocitidine 
• 83966-99-8 3',5'-di-O-acetyl-2'-deoxy-2'-fluoro-5-iodocytosine hydrochloride 

Downstream Products

• 182495-82-5 O₅'-dimethoxytrityl-N₄-benzoyl-5-methyl-2'-deoxy-2'-(R)-fluorocytidine 
• 1244969-83-2 3-[5-0-(4,4'-dimethoxytrityl)-(2-fluoro-2-deoxy-β-D-erythro-pentofuranosyl)]pyrido[2,3-d]pyrimidine-2,7(8H)-dione 3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite 
• 1188531-07-8 C₃₃H₃₀FN₃O₇ 
• 1244969-68-3 C₃₀H₂₃FIN₃O₇ 

Relevant articles and documents

Synthesis of (R)-Configured 2′-Fluorinated mC, hmC, fC, and caC Phosphoramidites and Oligonucleotides

Investigation of the function of the new epigenetic bases requires the development of stabilized analogues that are stable during base excision repair (BER). Here we report the synthesis of 2′-(R)-fluorinated versions of the phosphoramidites of 5-methylcy

NON-NATURAL RIBONUCLEOTIDES, AND METHODS OF USE THEREOF

One aspect of the present invention relates to modified nucleosides and oligonucleotides comprising such modified nucleosides. Another aspect of the invention relates to a method of inhibiting the expression of a gene in call, the method comprising (a) co

Synthesis and anti-viral activity of a series of D- and l-2′-deoxy-2′-fluororibonucleosides in the subgenomic HCV replicon system

Based on the discovery of (2′R)-D-2′-deoxy-2′- fluorocytidine as a potent anti-hepatitis C virus (HCV) agent, a series of D- and L-2′-deoxy-2′-fluororibonucleosides with modifications at 5- and/or 4-positions were synthesized and evaluated for their in vitro activity against HCV and bovine viral diarrhea virus (BVDV). The key step in the synthesis, the introduction of 2′-fluoro group, was achieved by either fluorination of 2,2′-anhydronucleosides with hydrogen fluoride-pyridine or potassium fluoride, or a fluorination of arabinonucleosides with DAST. Among the 27 analogues synthesized, only the 5-fluoro compound, namely (2′R)-D-2′-deoxy-2′,5-difluorocytidine (13), demonstrated potent anti-HCV activity and toxicity to ribosomal RNA. The replacement of the 4-amino group with a thiol group resulted in the loss of activity, while the 4-methylthio substituted analogue (25) exhibited inhibition of ribosomal RNA. As N4-hydroxycytidine (NHC) had previously shown potent anti-HCV activity, we combined the two functionalities of the N4-hydroxyl and the 2′-fluoro into one molecule, resulting (2′R)-D-2′-deoxy- 2′-fluoro-N4-hydroxycytidine (23). However, this nucleoside showed neither anti-HCV activity nor toxicity. All the L-forms of the analogues were devoid of anti-HCV activity. None of the compounds showed anti-BVDV activity, suggesting that the BVDV system cannot always predict anti-HCV activity.