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

Uses

3''-Amino-2'',3''-dideoxycytidine CAn be used to recognized Cytidine Deaminase. In doing so it can be effective in the treatment of leukemia.

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.

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.