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
• Article Data: 6

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

Description

3'-amino-2',3'-dideoxycytidine, also known as 3'-amino-2',3'-dideoxycytidine, is a nucleoside analog with a unique chemical structure. It is characterized by the presence of an amino group at the 3' position and the absence of a hydroxyl group at both the 2' and 3' positions of the sugar moiety. This modification enhances its stability and bioavailability, making it a promising candidate for various therapeutic applications.

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 
• 142820-94-8 3'-azido-2',3'-dideoxy-5'-O-tritylcytidine 
• 84472-85-5 Navuridine 
• 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 
• 84472-88-8 5'-O-acetyl-3'-azido-2',3'-dideoxy-4-chlorouridine 
• 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 
• 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 

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.

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.

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).