84472-86-6

Basic information

• Product Name: 3'-amino-2',3'-dideoxyuridine
• Synonyms: 3'-amino-2',3'-dideoxyuridine;AMDU;3'-NH2-ddU;5-(azidomethyl)-1-((2R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione;5-(azidomethyl)-2′-deoxyuridine (AmdU)
• CAS NO: 84472-86-6
• Molecular Formula: C9H13N3O4
• Molecular Weight: 227.22
• Mol File: 84472-86-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 174-176℃
• Appearance: /
• Density: 1.425
• CAS DataBase Reference: 3'-amino-2',3'-dideoxyuridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-amino-2',3'-dideoxyuridine(84472-86-6)
• EPA Substance Registry System: 3'-amino-2',3'-dideoxyuridine(84472-86-6)

Safety Data

• Hazardous Substances Data: 84472-86-6(Hazardous Substances Data)

Usage

General Description

3'-amino-2',3'-dideoxyuridine, also known as 3'-amino-ddU, is a chemical compound that is a nucleoside analog of uridine. It is often used in scientific research as a tool to study DNA and RNA synthesis due to its ability to inhibit DNA polymerase and reverse transcriptase. 3'-amino-2',3'-dideoxyuridine has also been explored for its potential antiviral properties, particularly against HIV, the virus that causes AIDS. 3'-amino-2',3'-dideoxyuridine is interesting to researchers because of its unique structure, which lacks a 3' hydroxyl group, making it resistant to degradation by cellular enzymes. This chemical has the potential to be a valuable tool in the development of new antiviral medications and as a probe for studying nucleic acid synthesis and function.

Upstream product

• 84472-85-5 Navuridine 
• 132149-43-0 5'-O-Acetyl-2',3'-dideoxy-3'-phthalimidouridine 
• 101039-97-8 1-((2R,4S,5S)-5-Hydroxymethyl-4-isopropylideneamino-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 84472-84-4 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)uracil 
• 14270-73-6 O^5'-trityl-2'-deoxy-uridine 
• 6038-53-5 1-<2-deoxy-3-O-methanesulfonyl-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl>uracil 
• 5983-03-9 3'-O-(methylsulfonyl)-5'-O-trityl-2'-deoxyuridine 
• 84472-83-3 1-[2-deoxy-5-O-(triphenylmethyl)-β-D-xylofuranosyl]uracil 
• 5964-40-9 2,3'-anhydro-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil 
• 123212-51-1 1,5-Di-O-acetyl-2,3-dideoxy-3-phthalimido-β-D-erythro-pentofuranose 
• 951-78-0 2'-deoxyuridine 
• 85236-87-9 1-(3-chloro-2,3-dideoxy-β-D-threo-pentofuranosyl)-2,4(1H,3H)-pyrimidinedione 
• 85236-88-0 1-<3-chloro-2,3-dideoxy-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl>-2,4(1H,3H)-pyrimidinedione 

Downstream Products

• 96699-73-9 3'-<3-(2-chloroethyl)-3-nitrosoureido>-2',3'-dideoxyuridine 

Relevant articles and documents

Synthesis of 3'-(4-nitroimidazo-1-yl)-2',3'-dideoxynucleosides of pyrimidine analogues and their biological evaluation against HIV

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A facile procedure for the reduction of azido nucleosides to amines using polymer bound triphenylphosphine

A very convenient reduction of azido nucleosides to amines under mild conditions using polystyryl diphenylphosphine resin is described. The method requires only a filtration and evaporation process for product isolation.

Synthesis and biological activity of 3'-azido- and 3'-amino substituted nucleoside analogs

The product distribution obtained in the reaction of 1-(5-0-trityl-0-mesyl-2-deoxy-β-D-erythro-pentofuranosyl)-2,4-(1H, 3H)-pyrimidinedione with lithium azide in N, N'-dimethylformamide at 100°C depends on the nature of the substituent in 5. The results may be explained by a difference in the acidity of the pyrimidinedione. The reaction of the more acidic nucleosides (X = I, F) appears to proceed preferentially through the 2,3'-anhydro intermediate, whereas for the less acidic products (X = H, CH3) direct nucleophilic displacement by the azide ion predominates. The different 3'-azidfo derivatives were reduced to 3'-amino compounds. All 3'-azido- and 3'-aminopyrimidine nucleosides were tested against herpes simplex virus, vaccinia and vesicular stomatitis virus and on murine L1210 cell growth. None of the substances exhibited significant activity.