84472-87-7

Basic information

• Product Name: 1-(5-O-acetyl-2,3-dideoxy-3-triaza-1,2-dien-2-ium-1-ylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione
• CAS NO: 84472-87-7
• Molecular Formula: C₁₁H₁₄N₅O₅
• Molecular Weight: 296.2588
• Mol File: 84472-87-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-(5-O-acetyl-2,3-dideoxy-3-triaza-1,2-dien-2-ium-1-ylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(5-O-acetyl-2,3-dideoxy-3-triaza-1,2-dien-2-ium-1-ylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione(84472-87-7)
• EPA Substance Registry System: 1-(5-O-acetyl-2,3-dideoxy-3-triaza-1,2-dien-2-ium-1-ylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione(84472-87-7)

Safety Data

• Hazardous Substances Data: 84472-87-7(Hazardous Substances Data)

Usage

Chemical structure

A complex chemical compound with a pyrimidine-2,4(1H,3H)-dione structure.

Pentofuranosyl group

Contains a pentofuranosyl group linked to a pyrimidine ring.

O-acetyl group

Modified with an O-acetyl group.

2,3-dideoxy-3-triaza-1,2-dien-2-ium-1-yl moiety

Contains a 2,3-dideoxy-3-triaza-1,2-dien-2-ium-1-yl moiety.

Pharmaceutical applications

Has potential pharmaceutical applications due to its structure and properties.

Further research

Further research and testing is necessary to fully understand its potential uses and benefits.

Upstream product

• 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 
• 84472-84-4 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)uracil 
• 84472-85-5 Navuridine 
• 108-24-7 acetic anhydride 

Downstream Products

• 105784-82-5 3'-Azido-2',3'-dideoxy-5-bromouridine 
• 84472-89-9 3'-azido-2',3'-dideoxycytidine 
• 84472-90-2 3'-amino-2',3'-dideoxycytidine 
• 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 

Relevant articles and documents

Tosvinyl and besvinyl as protecting groups of imides, azinones, nucleosides, sultams, and lactams. Catalytic conjugate additions to tosylacetylene

The use of the 2-(4-methylphenylsulfonyl)-ethenyl (tosvinyl, Tsv) group for the protection of the NH group of a series of imides, azinones (including AZT), inosines, and cyclic sulfonamides has been examined. The Tsvprotected derivatives are obtained in excellent yields by conjugate addition to tosylacetylene (ethynyl p-tolyl sulfone). The stereochemistry of the double bond can be controlled at will: with only 1 mol % of Et3N or with catalytic amounts of NaH, the Z stereoisomers are generated almost exclusively, while the E isomers are obtained using a stoichiometric amount of DMAP. Analogous phenylsulfonylvinyl-protected groups (with the besvinyl or Bsv group instead of Tsv) are obtained stereospecifically by reaction with (Z)- or (E)-bis(phenylsulfonyl)ethene. For lactams and oxazolidinones, this last method is much better. The Tsv and Bsv groups are stable in the presence of non-nucleophilic bases and to acids. They can be removed highly effectively via a conjugate addition-elimination mechanism using pyrrolidine or sodium dodecanethiolate as nucleophiles.

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.