84472-84-4

Basic information

• Product Name: Uridine, 3'-azido-2',3'-dideoxy-5'-O-(triphenylMethyl)-
• Synonyms: Uridine, 3'-azido-2',3'-dideoxy-5'-O-(triphenylMethyl)-
• CAS NO: 84472-84-4
• Molecular Formula: C₂₈H₂₅N₅O₄
• Molecular Weight: 495.5292
• Mol File: 84472-84-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 67-70 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: Uridine, 3'-azido-2',3'-dideoxy-5'-O-(triphenylMethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine, 3'-azido-2',3'-dideoxy-5'-O-(triphenylMethyl)-(84472-84-4)
• EPA Substance Registry System: Uridine, 3'-azido-2',3'-dideoxy-5'-O-(triphenylMethyl)-(84472-84-4)

Safety Data

• Hazardous Substances Data: 84472-84-4(Hazardous Substances Data)

Usage

General Description

Uridine, 3'-azido-2',3'-dideoxy-5'-O-(triphenylMethyl)-, also known as AZT-UDP, is a modified form of uridine. It is a nucleoside analogue that is commonly used as an antiviral drug for the treatment of HIV/AIDS. AZT-UDP works by inhibiting the reverse transcriptase enzyme, which is essential for the replication of the HIV virus. It is a potent inhibitor of viral replication and has been widely used in combination with other antiretroviral drugs to effectively manage HIV infection. Additionally, AZT-UDP has also been studied for its potential use in cancer treatment due to its ability to interfere with DNA synthesis and cell replication.

InChI:InChI=1/C28H25N5O4/c29-32-31-23-18-26(33-17-16-25(34)30-27(33)35)37-24(23)19-36-28(20-10-4-1-5-11-20,21-12-6-2-7-13-21)22-14-8-3-9-15-22/h1-17,23-24,26,29H,18-19H2/p+1

Upstream product

• 5964-40-9 2,3'-anhydro-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil 
• 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 
• 14270-73-6 O^5'-trityl-2'-deoxy-uridine 
• 84472-83-3 1-[2-deoxy-5-O-(triphenylmethyl)-β-D-xylofuranosyl]uracil 
• 951-78-0 2'-deoxyuridine 
• 76-83-5 trityl chloride 

Downstream Products

• 127492-39-1 1-((2R,4S,5S)-4-Azido-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-chloro-1H-pyrimidine-2,4-dione 
• 84472-86-6 3'-amino-2',3'-dideoxyuridine 
• 84472-90-2 3'-amino-2',3'-dideoxycytidine 
• 84472-89-9 3'-azido-2',3'-dideoxycytidine 
• 84472-87-7 3'-azido-2',3'-dideoxy-5'-O-acetyluridine 
• 859206-78-3 3'-amino-5'-O-trityl-2',3'-dideoxyuridine 
• 859206-79-4 3'-acetylamino-5'-O-trityl-2',3'-dideoxyuridine 

Relevant articles and documents

Modified 5'-Trityl Nucleosides as Inhibitors of Plasmodium falciparum dUTPase

2'-Deoxyuridine triphosphate nucleotidohydrolase (dUTPase) is a potential drug target for the treatment of malaria. We previously reported the discovery of 5'-tritylated analogues of deoxyuridine as selective inhibitors of this Plasmodium falciparum enzyme. Herein we report further structure-activity studies; in particular, variations of the 5'-trityl group, the introduction of various substituents at the 3'-position of deoxyuridine, and modifications of the base. Compounds were tested against both the enzyme and the parasite. Variations of the 5'-trityl group and of the 3'-substituent were well tolerated and yielded active compounds. However, there is a clear requirement for the uracil base for activity, because modifications of the uracil ring result in loss of enzyme inhibition and significant decreases in antiplasmodial action. Fewer trips to the dUMP: dUTPase is a potential drug target for the treatment of malaria. We previously reported the discovery of 5'-tritylated analogues of deoxyuridine as selective inhibitors of this P.falciparum enzyme. Herein we report further structure-activity studies of the 5'-trityl group, the introduction of various substituents at the 3'-position of deoxyuridine, and modifications of the base.

5'-Diphosphohexose nucleoside pharmaceutical compositions

Compounds of the general formula: STR1 wherein A, B, and C are hydrogen, halogen, or azido; D is hydrogen, halogen, azido, or OH; A and B or C and D can be replaced with a double bond; R is an aldohexose, aldohexosamine, or N-acetyl aldohexosamine, R

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.