54-25-1

Basic information

• Product Name: 6-AZAURIDINE
• Synonyms: AZAURIDINE, 6-;6-AZA-2,4-DIHYDROXYPYRIMIDINE RIBOSIDE;6-AZAURIDINE MONOHYDRATE;6-AZAURACIL RIBOSIDE;6-AZAURACIL RIBOSIDE MONOHYDRATE;6-AZAURIDINE;2-BETA-D-RIBOFURANOSYL-1,2,4-TRIAZINE-3,5(2H,4H)-DIONE;2-beta-d-ribofuranosyl-1,2,4-triazin-3,5(2h,4h)-dion
• CAS NO: 54-25-1
• Molecular Formula: C₈H₁₁N₃O₆
• Molecular Weight: 245.19
• EINECS: 200-199-6
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Antibiotic Explorer
• Mol File: 54-25-1.mol

Chemical Properties

• Melting Point: 157-159 °C(lit.)
• Boiling Point: 388.15°C (rough estimate)
• Flash Point: °C
• Appearance: White/Powder
• Density: 1.4866 (rough estimate)
• Refractive Index: 1.7950 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated), Pyridine (Slightly), Water
• PKA: 6.70(at 25℃)
• Water Solubility: It is soluble in water.
• Stability: Hygroscopic
• Merck: 14,904
• CAS DataBase Reference: 6-AZAURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AZAURIDINE(54-25-1)
• EPA Substance Registry System: 6-AZAURIDINE(54-25-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36
• WGK Germany: 3
• RTECS: XY8575000
• Hazardous Substances Data: 54-25-1(Hazardous Substances Data)

Usage

Uses

Used in Antiviral Studies:
6-Azauridine is used as an antiviral agent for its ability to inhibit de novo pyrimidine synthesis and DNA synthesis. It is converted intracellularly into mono, di, and triphosphate derivatives, which incorporate into RNA and inhibit protein synthesis, making it a valuable compound in antiviral research.
Used in Anticancer Applications:
In the field of cancer research, 6-Azauridine is utilized as an antineoplastic antimetabolite. It interferes with pyrimidine biosynthesis, thereby preventing the formation of cellular nucleic acids, which is crucial for cancer cell growth and proliferation.
Used in Antipsoriatic Treatment:
6-Azauridine, particularly in its triacetate form, is effective as an antipsoriatic agent. It is used to treat skin conditions like psoriasis, where it helps to regulate the overproduction of skin cells.
Used in Cell Formation Studies:
6-Azauridine is also employed in research on cell formation, as it blocks the conversion of orotic acid into UMP, providing insights into the processes involved in cellular development and function.

Biochem/physiol Actions

6-azauridine is a prodrug, upon conversion to 6-aza-UMP, inhibits uridine monophosphate synthase (UMPS). It is a broad spectrum anti-metabolite. It interferes with pyrimidine biosynthesis and affects the cellular nucleic acid levels. It is considered as a antineoplastic metabolite. It inhibits RNA viruses like chikungunya virus, semliki forest virus, and human coronavirus. It significantly inhibits the growth of Cryptosporidium parasites.

InChI:InChI=1/C8H11N3O6/c12-2-3-5(14)6(15)7(17-3)11-8(16)10-4(13)1-9-11/h1,3,5-7,12,14-15H,2H2,(H,10,13,16)

Upstream product

• 2169-64-4 2',3',5'-tri-O-acetyl-6-azauridine 
• 59967-97-4 6-azauridine 2',3'-O-carbonate 
• 461-89-2 6-azauracil 

Downstream Products

• 170743-87-0 5-O-tosyl-2',3'-O-ethoxymethylidene-6-azauridine 
• 14528-15-5 6-azacytidine 
• 2018-19-1 6-aza-uridine 5'-monophosphate 
• 2169-64-4 2',3',5'-tri-O-acetyl-6-azauridine 
• 138779-27-8 N³-α-Phenylethyl-6-azauridine 
• 138779-24-5 N³-o-Xylyl-6-azauridine 
• 138779-28-9 N³-β-Phenylethyl-6-azauridine 
• 138779-26-7 N³-p-Xylyl-6-azauridine 
• 138779-25-6 N³-m-Xylyl-6-azauridine 
• 138779-23-4 N³-Benzyl-6-azauridine 
• 170936-97-7 5'-O-tosyl-6-azauridine 
• 54898-50-9 (5aR)-8c-benzoyloxy-7t-benzoyloxymethyl-(5ar,8ac)-5a,7,8,8a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-b][1,2,4]triazin-2-one 

Relevant articles and documents

New non-aromatic triazinic nucleosides : Synthesis and antiretroviral evaluation of β-ribosylamine nucleoside analogs

Various 5-alkyl-6-aza-5,6-dihydrouridines and 6-(β-D-ribopyranosyl)-5-alkyl-6-aza-5,6-dihydrouracils have been synthesized. A new regioselective method is described for coupling triazinic bases to the sugar unit. Different epimers were isolated. Antiretroviral activity against Visna virus was evaluated.

Hydrolysis of the prodrug, 2',3',5'-triacetyl-6-azauridine

Purpose. The purposes were to study the kinetics of hydrolysis of 2',3',5'-triacetyl-6-azauridine (1) in aqueous solution (μ = 0.5) and to identify the main intermediates and products of the reaction. Methods. A stability indicating isocratic LC assay was used to study the rate of degradation of 1. A gradient LC assay was used to study the time courses of the degradants. The products of hydrolysis were isolated by preparative liquid chromatography and identified by 1H-NMR and CI-MS. The pK(a) value was obtained by potentiometric titration. Results. At 36.8°C, the pH-rate profile of 1 in water was adequately described by a four-term rate equation. The intermediates were identified as the primary and secondary di-acetates, and the primary and secondary mono-acetates. The final product was 6-azauridine. Conclusions. A simplified kinetic scheme could be used to describe the concentration-time profiles of 1, the intermediates and the final product.

2',3'-O-CARBONYL DERIVATIVES OF 6-AZAURIDINE IN THE SYNTHESIS OF ITS 5'-SUBSTITUTED AND 5'-DEOXY DERIVATIVES

Preparation of 2',3'-O-carbonyl derivatives of 5'-deoxy-6-azauridine and 6-azauridine using 1,1'-carbonyldiimidazole has been elaborated. 5'-Chloro and 5'-bromo derivatives were prepared by treatment of the 5'-O-mesyl derivative with quarternary ammonium halides, 5'-chloro derivatives also by direct halogenation with thionyl chloride in hexamethylphosphortriamide or with tetrachloromethane, triphenyl phosphine, and dimethylformamide.Derivatives of 5'-bromo-6-azauridine were reduced with tributyltin hydride to 5'-deoxy-6-azauridine compounds. 6-Azauridine 2',3'-carbonate (IVa) and its 5'-derivatives IVc and IVe on treatment with imidazole in dimethylformamide afforded 2,2'-anhydronucleosides IIIa-IIIc.The 2,2'-anhydro-5'-deoxy compound IIIc underwent alkaline hydrolysis to 5'-deoxy-1-β-D-arabino-pentofuranosyl-6-azauracil (VIa).Treatment of 2,2'-anhydro-5'-deoxy-5'-chloro derivative IIIb with hydrogen chloride led to 2',5'-dichloro derivative If.