84472-89-9

Basic information

• Product Name: 3'-AZIDO-2'-DEOXY-D-CYTIDINE
• Synonyms: 3'-AZIDO-2'-DEOXY-D-CYTIDINE;2',3'-Dideoxy-3'-azidocytidine;3'-Azido-2',3'-dideoxy-4-deoxo-4-iminouridine;Nsc382318;3'-Az-ddC;3'-Azido-2', 3'-dideoxycytidine;CS 91
• CAS NO: 84472-89-9
• Molecular Formula: C₉H₁₂N₆O₃
• Molecular Weight: 266.26
• Mol File: 84472-89-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3'-AZIDO-2'-DEOXY-D-CYTIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-AZIDO-2'-DEOXY-D-CYTIDINE(84472-89-9)
• EPA Substance Registry System: 3'-AZIDO-2'-DEOXY-D-CYTIDINE(84472-89-9)

Safety Data

• Hazardous Substances Data: 84472-89-9(Hazardous Substances Data)

Usage

General Description

3'-Azido-2'-deoxy-D-cytidine is a synthetic nucleoside analog that has been studied for its potential antiviral properties, particularly against HIV and hepatitis B. It is a modified form of the natural nucleoside cytidine, in which an azido group is added to the 3' position of the sugar ring. This modification has been shown to inhibit the replication of certain viruses by interfering with their ability to create new DNA strands. This makes it a promising candidate for the development of new antiviral drugs. Additionally, 3'-azido-2'-deoxy-D-cytidine has been used as a tool in biochemistry and molecular biology research, particularly in the study of nucleic acid synthesis and repair.

Upstream product

• 84472-85-5 Navuridine 
• 87190-76-9 Acetic acid (2S,3S,5R)-3-azido-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 84472-88-8 5'-O-acetyl-3'-azido-2',3'-dideoxy-4-chlorouridine 
• 142820-94-8 3'-azido-2',3'-dideoxy-5'-O-tritylcytidine 
• 170236-34-7 N₄-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2,3-anhydro-2'-deoxycytidine 
• 4836-13-9 N₄-benzoyl-2'-deoxycytidine 
• 170236-48-3 Methanesulfonic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 
• 84472-84-4 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)uracil 
• 84472-87-7 3'-azido-2',3'-dideoxy-5'-O-acetyluridine 
• 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 
• 951-78-0 2'-deoxyuridine 

Downstream Products

• 84472-90-2 3'-amino-2',3'-dideoxycytidine 

Relevant articles and documents

Synthesis and application of 3′-amino-dye-terminators for dna sequencing

The synthesis of 3′-aminomodified nucleoside 5′-triphosphates and their coupling with oligoaminoacid-linked dyes is described. Application for DNA dye-terminator sequencing was investigated. Copyright 1997 by Marcel Dekker, Inc.

Chemical-enzymatic synthesis of 3'-amino-2',3'-dideoxy-β-D- ribofuranosides of natural heterocyclic bases and their 5'-monophosphates

Treatment of O2,3'-anhydro-5'-O-trityl derivatives of thymidine (1) and 2'-deoxyuridine (2) with lithium azide in dimethylformamide at 150 °C resulted in the formation of the corresponding isomeric 3'-azido-2',3'- dideoxy-5'-O-trityl-β-D-ribofuranosyl N1- (the major products) and N3- nucleosides 3/4 and 5/6). 3'-Amino-2',3'-dideoxy-β-D-ribofuranosides of thymidine [Thd(3'NH2)], uridine [dUrd(3'NH2)], and cytidine [dCyd(3'NH2)] were synthesized from the corresponding 3'-azido derivatives. The Thd(3'NH2) and dUrd(3'NH2) were used as donors of carbohydrate moiety in the reaction of enzymatic transglycosylation of adenine and guanine to afford dAdo(3'NH2) and dGuo(3'NH2). The substrate activity of dN(3'NH2) vs. nucleoside phosphotransferase of the whole cells of Erwinia herbicola was studied.

Synthesis and Biological Activity of Various 3'-Azido and 3'-Amino Analogues of 5-Substituted Pyrimidine Deoxyribonucleosides

Various new 5-substituted 3'-azido- and 3'-amino derivatives of 2'-deoxyuridine and 2'-deoxycytidine have been synthesized and biologically evaluated.Among these compounds, 3'-amino-2',3'-dideoxy-5-fluorouridine (3), 3'-amino-2',3'-dideoxycytidine (7a), and 3'-amino-2',3'-dideoxy-5-fluorocytidine (7c) were found to be the most active against murine L1210 and sarcoma 180 neoplastic cells in vitro, with an ED50 of 15 and 1 μM, 0.7 and 4 μM, and 10 and 1 μM, respectively.The 3'-azido derivatives, 2 and 6c, were less active in comparison with their 3'-amino counterparts.In addition, the 5-fluoro-3'-amino nucleosides, 3 and 7c, were tested against L1210 leukemia bearing CDF1 mice.Our preliminary findings indicate that compound 7c (6 * 200 mg/kg) was as active as the positive control, 5-fluorouracil (6 * 20 mg/kg), yielding a T/C * 100 of 146 and 129, respectively.However, 3 was found to be inactive in this experiment.