2169-64-4

Basic information

• Product Name: 6-AZAURIDINE 2',3',5'-TRIACETATE
• Synonyms: 2μ,3μ,5μ-Tri-O-acetyl-6-azauridine, 6-Azauridine 2μ,3μ,5μ-triacetate, 6-AzUrd-TA, Azaribine, 2-β-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione 2μ,3μ,5μ-triacetate;6-Azauridine 2μ,3μ,5μ-triacetate, 6-AzUrd-TA, Azaribine;2-(2-O,3-O,5-O-Triacetyl-β-D-ribofuranosyl)-1,2,4-triazine-3,5(2H,4H)-dione;6-Azauridine 2',3',5'-triacetate,98%;2-(2’,3’,5’-triacetyl-beta-d-ribofuranosyl)-as-triazine-3,5-(2h,4h)-dione;2’,3’,5’-triacetyl-6-azauridine;4h)-dione,2-(2’,3’,5’-triacetyl-beta-d-ribofuranosyl)-as-triazine-5-(2h;cb304
• CAS NO: 2169-64-4
• Molecular Formula: C₁₄H₁₇N₃O₉
• Molecular Weight: 371.3
• EINECS: 218-515-6
• Mol File: 2169-64-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 99-101 °C(lit.)
• Boiling Point: 501.01°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.3535 (rough estimate)
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 6-AZAURIDINE 2',3',5'-TRIACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AZAURIDINE 2',3',5'-TRIACETATE(2169-64-4)
• EPA Substance Registry System: 6-AZAURIDINE 2',3',5'-TRIACETATE(2169-64-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 2
• RTECS: XY8577000
• Hazardous Substances Data: 2169-64-4(Hazardous Substances Data)

Usage

Description

6-AZAURIDINE 2',3',5'-TRIACETATE, also known as Triazure, Cb 304, or Ribo-azauracil, is a N-glycosyl-1,2,4-triazine derivative that is 6-azauridine acetylated at positions 2', 3', and 5' on the sugar ring. It serves as a prodrug for 6-azauridine and is primarily used for the treatment of psoriasis.

Uses

Used in Pharmaceutical Industry:
6-AZAURIDINE 2',3',5'-TRIACETATE is used as an anti-psoriatic agent for the treatment of psoriasis. It acts as a prodrug for 6-azauridine, which helps in reducing the symptoms and severity of the skin condition.
Used in Dermatology:
In the field of dermatology, 6-AZAURIDINE 2',3',5'-TRIACETATE is used as a therapeutic agent for managing psoriasis. Its application helps in alleviating the inflammation and scaling associated with the disease, improving the patient's quality of life.
Brand Name:
Triazure (Parke-Davis) is a well-known brand name for 6-AZAURIDINE 2',3',5'-TRIACETATE, which is used for the treatment of psoriasis.

World Health Organization (WHO)

Azaribine, an antineoplastic agent, was introduced in 1975 for the treatment of severe, recalcitrant, disabling arthritis. Following reports of thromboembolic and thrombotic reactions, the drug was withdrawn in the USA in 1976. The causal relationship between azaribine and these events has been questioned and the drug remains available in the USA for investigational purposes.

Upstream product

• 108-24-7 acetic anhydride 
• 54-25-1 6-Azauridine 
• 17331-61-2 3,5-bis(trimethylsilyloxy)-1,2,4-triazine 
• 13035-61-5 1,2,3,5-tetraacetylribose 

Downstream Products

• 54-25-1 6-Azauridine 
• 10276-30-9 6-azauridine 5'-acetate 
• 14528-15-5 6-azacytidine 

Relevant articles and documents

A new simple nucleoside synthesis

Persilylation of excess D-ribose or D-glucose with 6-azauracil or N6-benzoyl-adenine followed by condensation with trimethylsilyl triflate in acetonitrile at 80° affords the corresponding persilylated nucleosides. Transsilylation with methanol and chromatography on SiO2 give the pure free nucleosides in up to 70% yield.

THERAPEUTIC FOR HEPATIC CANCER

A novel pharmaceutical composition for treating or preventing hepatocellular carcinoma and a method of treatment are provided. A pharmaceutical composition for treating or preventing liver cancer is obtained by combining a chemotherapeutic agent with an anti-glypican 3 antibody. Also disclosed is a pharmaceutical composition for treating or preventing liver cancer which comprises as an active ingredient an anti-glypican 3 antibody for use in combination with a chemotherapeutic agent, or which comprises as an active ingredient a chemotherapeutic agent for use in combination with an anti-glypican 3 antibody. Using the chemotherapeutic agent and the anti-glypican 3 antibody in combination yields better therapeutic effects than using the chemotherapeutic agent alone, and mitigates side effects that arise from liver cancer treatment with the chemotherapeutic agent.

Biochemical detection of cytidine protonation within RNA

Perturbation of active site functional group pK(a)s is an important strategy employed by protein enzymes to achieve catalysis. There is increasing evidence to indicate that RNAs also utilize functional group pK(a) perturbation for folding and reactivity. One of the best candidates for a functionally relevant pK(a) perturbation is the N3 of C (pK(a) 4.2), which could be sufficiently raised to allow protonation near physiological pH. Here we report the synthesis and use of a series of α-phosphorothioate tagged cytidine analogues whose altered N3 pK(a)s make it possible to efficiently detect functionally relevant protonation events by nucleotide analogue interference mapping. 6-Azacytidine (n6CαS) and 5-fluorocytidine (f5CαS) both have enhanced acidity at the N3 position (pK(a) 2.6 and 2.3, respectively) but leave the hydrogen bonding face of C otherwise unaffected. In contrast, pseudoisocytidine (ΨiCαS) is a charge neutral analogue that mimics the hydrogen bonding character of protonated C. To test the utility of these analogues, we characterized the C300+-G97-C277 mutant form of the Tetrahymena group I intron, which is predicted to require C300 protonation for ribozyme folding and reactivity. At neutral to alkaline pHs, C300 was the only site of n6CαS and f5Cαs interference within the intron, yet both interferences were rescued at acidic pH. Furthermore, ΨiCαS substitution at C300 resulted in enhanced activity at alkaline pHs, consistent with the presence of an N3 proton under the pH conditions studied. Interference mapping with these analogues provides an efficient and sensitive means to identify every site within an RNA where cytidine protonation is important for RNA function and may make it possible to identify C's that participate in general acid/base catalysis within ribozyme active sites.