139442-01-6

Basic information

• Product Name: 4'-C-azidouridine
• Synonyms: 4'-C-azidouridine;4'-alpha-Azidouridine;Uridine, 4'-azido-;Uridine, 4'-C-azido-;1-(4'-Azido-beta-D-ribofuranosyl)uracil;1-[(2R,3R,4S,5R)-5-azido-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS NO: 139442-01-6
• Molecular Formula: C₉H₁₁N₅O₆
• Molecular Weight: 285.21354
• Mol File: 139442-01-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 4'-C-azidouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-C-azidouridine(139442-01-6)
• EPA Substance Registry System: 4'-C-azidouridine(139442-01-6)

Safety Data

• Hazardous Substances Data: 139442-01-6(Hazardous Substances Data)

Usage

General Description

4'-C-azidouridine is a modified nucleoside that contains an azido group at the 4' carbon position of the ribose ring. It is commonly used in bioorthogonal labeling and click chemistry for the specific and efficient labeling of RNA molecules in cellular and in vivo systems. This chemical tool allows for the selective modification of RNA with minimal perturbation to its function, making it a valuable tool for studying RNA biology and function. Additionally, 4'-C-azidouridine has been explored as a potential antiviral agent, as it exhibits inhibitory activity against the replication of certain viruses, including hepatitis C virus and Zika virus. Its unique properties and potential applications make 4'-C-azidouridine an important chemical compound in the fields of molecular biology, virology, and drug discovery.

InChI:InChI=1/C9H11N5O6/c10-13-12-9(3-15)6(18)5(17)7(20-9)14-2-1-4(16)11-8(14)19/h1-2,5-7,15,17-18H,3H2,(H,11,16,19)/t5-,6+,7-,9-/m1/s1

Upstream product

• 139419-02-6 4'-azido-2',3'-di-O-benzoyl-5'-deoxy-5'-iodouridine 
• 478182-26-2 C₂₃H₁₉N₅O₈ 
• 139419-04-8 4'-azido-5'-deoxy-5'-iodouridine 
• 14365-63-0 5'-deoxyuridin-4'-ene 
• 812647-80-6 1-(4’-azido-5‘-O-(3-chloro)benzoyl-2’,3‘-O-dibenzoyl-β-D-ribofuranosyl)uracil 
• 1365255-42-0 C₃₀H₂₃N₅O₉ 
• 58-96-8 uridine 

Downstream Products

• 478182-28-4 4'-azidocytidine 
• 876707-99-2 2,2'-anhydro-1-(4'-azido-β-D-arabinofuranosyl)uracil 
• 690271-27-3 4'-azido-2',3'-O-isopropylidenyluridine-4'-azido-2',3'-O-isopropylidenyluridine 
• 1145869-38-0 1-(4'-azido-2',5'-di-O-trityl-β-D-ribofuranosyl)uracil 
• 1365255-42-0 C₃₀H₂₃N₅O₉ 
• 1365255-42-0 C₃₀H₂₃N₅O₉ 
• 690270-09-8 benzoic acid (2R,3S,4R,5R)-2-azido-3,4-dibenzoyloxy-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydrofuran-2-ylmethyl ester 
• 876708-01-9 1-(4'-azido-β-D-arabinofuranosyl)uracil 
• 1365255-68-0 4'-azidouridine-5'-(O-phenyl-N-(S)-1-(isopropoxycarbonyl)eth-1-yl)thiophosphoramidate 
• 1365255-71-5 4'-azidouridine-5'-(O-phenyl-N-(S)-neopentoxycarbonyleth-1-yl)thiophosphoramidate 

Relevant articles and documents

4'-AZIDO SUBSTITUTED NUCLEOSIDE DERIVATIVES AS INHIBITORS OF EBOLA VIRUS RNA REPLICATION

The application discloses compounds of Formula I wherein the variable substituents are as defined herein. The compounds of Formula I and pharmaceutical compositions comprising compounds of Formula I are useful for the treatment of diseases mediated by Filoviruses such as Ebolavirus.

AZIDO NUCLEOSIDES AND NUCLEOTIDE ANALOGS

Disclosed herein are nucleosides, nucleotides and analogs thereof, pharmaceutical compositions that include one or more of nucleosides, nucleotides and analogs thereof, and methods of synthesizing the same. Also disclosed herein are methods of amelioratin

Anti-viral nucleosides

4-Amino-1-((2R,3S,4S,5R)-5-azido-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one (I:R1=R2=R3=R4=H) and prodrugs thereof are hepatitis C(HCV) polymerase inhibitors. Also disclosed are comp