84472-90-2

Basic information

• Product Name: 3'-amino-2',3'-dideoxycytidine
• Synonyms: 3'-amino-2',3'-dideoxycytidine;4-Amino-1-[4-amino-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;3'-NH2-ddC
• CAS NO: 84472-90-2
• Molecular Formula: C₉H₁₄N₄O₃
• Molecular Weight: 226.23
• Mol File: 84472-90-2.mol

Chemical Properties

• Boiling Point: 450.2 °C at 760 mmHg
• Flash Point: 226 °C
• Appearance: /
• Density: 1.73 g/cm³
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 3'-amino-2',3'-dideoxycytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-amino-2',3'-dideoxycytidine(84472-90-2)
• EPA Substance Registry System: 3'-amino-2',3'-dideoxycytidine(84472-90-2)

Safety Data

• Hazardous Substances Data: 84472-90-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3'-amino-2',3'-dideoxycytidine is used as an antiviral agent for the treatment of leukemia. It is particularly effective against various types of leukemia, including acute lymphoblastic leukemia (ALL) and chronic myeloid leukemia (CML). 3'-amino-2',3'-dideoxycytidine works by inhibiting the activity of cytidine deaminase, an enzyme that plays a crucial role in the replication and transcription of viral DNA. By targeting this enzyme, 3'-amino-2',3'-dideoxycytidine disrupts the viral life cycle and prevents the progression of leukemia.
Additionally, 3'-amino-2',3'-dideoxycytidine has been found to exhibit synergistic effects when combined with other antiviral agents, enhancing the overall therapeutic efficacy and providing a more effective treatment option for leukemia patients.

Upstream product

• 84472-89-9 3'-azido-2',3'-dideoxycytidine 
• 85236-96-0 3'-azido-2',3'-dideoxycytidine hydrochloride 
• 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 
• 84472-83-3 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 
• 84472-88-8 5'-O-acetyl-3'-azido-2',3'-dideoxy-4-chlorouridine 
• 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 
• 84472-85-5 Navuridine 
• 142820-94-8 3'-azido-2',3'-dideoxy-5'-O-tritylcytidine 

Downstream Products

• 899435-27-9 3'-NH-trityl-2',3'-dideoxycytidine 
• 195375-46-3 N₄-benzoyl-3'-aminotrityl-2',3'-dideoxycytidine 

Relevant articles and documents

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.

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 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.

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.

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).