84472-89-9

Usage

Uses

Used in Pharmaceutical Industry:
3'-AZIDO-2'-DEOXY-D-CYTIDINE is used as a potential antiviral agent for its ability to inhibit the replication of specific viruses such as HIV and hepatitis B. The modification of the natural cytidine allows it to interfere with the virus's capacity to create new DNA strands, making it a promising candidate for the development of new antiviral drugs.
Used in Biochemical and Molecular Biology Research:
In the field of biochemical and molecular biology research, 3'-AZIDO-2'-DEOXY-D-CYTIDINE is utilized as a research tool to study the mechanisms of nucleic acid synthesis and repair. Its unique structure allows scientists to investigate the processes involved in the maintenance and replication of genetic material, contributing to a deeper understanding of molecular biology.

Upstream product

• 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 
• 142820-94-8 3'-azido-2',3'-dideoxy-5'-O-tritylcytidine 
• 4836-13-9 N₄-benzoyl-2'-deoxycytidine 
• 951-78-0 2'-deoxyuridine 
• 85236-88-0 1-<3-chloro-2,3-dideoxy-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl>-2,4(1H,3H)-pyrimidinedione 
• 85236-87-9 1-(3-chloro-2,3-dideoxy-β-D-threo-pentofuranosyl)-2,4(1H,3H)-pyrimidinedione 
• 84472-83-3 1-[2-deoxy-5-O-(triphenylmethyl)-β-D-xylofuranosyl]uracil 
• 5983-03-9 3'-O-(methylsulfonyl)-5'-O-trityl-2'-deoxyuridine 
• 6038-53-5 1-<2-deoxy-3-O-methanesulfonyl-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl>uracil 
• 14270-73-6 O^5'-trityl-2'-deoxy-uridine 
• 84472-87-7 3'-azido-2',3'-dideoxy-5'-O-acetyluridine 
• 84472-84-4 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)uracil 
• 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 
• 170236-34-7 N₄-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2,3-anhydro-2'-deoxycytidine 

Downstream Products

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

Relevant academic research and scientific papers

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.

Synthesis and antileukemic activity of chymotrygsin-activated derivatives of 3'-amino-2',3'-dideoxycytidine. (Synthetic nucleosides and nucleotides. XXXIII

3'-Amino-2',3'-dideoxycytidine (8) was directly synthesized from 2'-deoxycytidine, 2',3'-Dideoxy-3'-(N-acyl-L-phenylalanylamino)cytidines (acyl =butoxycarbonyl (9a), acetyl (9b), benzoyl (9c), and α-hexanoyl (9d)) were synthesized as chymotrypsin-activated prodrugs of 8. This N-protection was required for activation by chymotrypsin to 8. In vitro, compound 8 showed high cytotoxic activity against P388 cells, but the prodrugs 9a-d were ineffective. In vitro, however, these prodrugs showed much higher activity than 8 in mice bearing P388 cells.

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.

3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: Synthesis and biological activities

3'-Amino-2',3'-dideoxyribonucleosides of thymine, uracil, and 5-iodouracil (1-3) were synthesized from the corresponding 2'-deoxyribonucleosides via the threo-3'-chloro and the erythro-3'-azido derivatives. Corresponding aminonucleosides of 5-bromouracil, 5-chlorouracil, and 5-fluorouracil (4-6) were synthesized enzymatically with 3'-amino-2',3'-dideoxythymidine as the aminopentosyl donor and thymidine phosphorylase (EC 2.4.2.4) as the catalyst. 3'-Amino-2',3'-dideoxycytidine (7) was synthesized by amination of the 3'-azido precursor of 3'-amino-2',3'-dideoxyuridine. The biological activity of 3'-amino-2',3'-dideoxy-5-fluorouridine (6) was notable among this group of aminonucleosides. It had an ED50 of 10 μM against adenovirus and was not appreciably cytotoxic to mammalian cells in culture. It also had activity against some Gram-positive bacteria but not against a variety of Gram-negative bacteria. The other aminonucleosides (1-5 and 7) lacked or exhibited weak antiviral and antibacterial activities. The only compounds in this group that were appreciably toxic to mammalian cells in culture were the thymidine and deoxycytidine analogues (1 and 7).

Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogues of pyrimidine deoxyribonucleoside

Several new 3'-azido and 3'-amino nucleosides (8, 9, 12, and 13) have been synthesized and their biological activities evaluated. Among them, 3'-amino-2',3'-dideoxycytidine (13) was found to exhibit potent cytotoxic activity against both L1210 and S-180 cells in vitro with an ID50 of 0.7 and 4.0 μM, respectively. Furthermore, 13 has also shown antitumor activity against L1210 tumor bearing mice with a T/C x 100 value of 283.

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.