461-89-2

Basic information

• Product Name: 6-Azauracil
• Synonyms: 4(6)-Azauracil;As-Triazine-3,5(2H,4H)-dione;As-Triazine-3,5-diol;Azauracil;AZU;IPO 3834;ipo3834;NSC 3425
• CAS NO: 461-89-2
• Molecular Formula: C₃H₃N₃O₂
• Molecular Weight: 113.07
• EINECS: 207-318-0
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;NULL
• Mol File: 461-89-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 274-275 °C(lit.)
• Boiling Point: 211.75°C (rough estimate)
• Flash Point: 258.3 °C
• Appearance: White to light yellow/Fine Crystalline Powder
• Density: 1.5988 (rough estimate)
• Refractive Index: 1.4264 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 7.78±0.20(Predicted)
• Water Solubility: Partly soluble in water, ethanol, DMSO, and 1 M NH4OH (50 mg/ml).
• BRN: 116472
• CAS DataBase Reference: 6-Azauracil(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Azauracil(461-89-2)
• EPA Substance Registry System: 6-Azauracil(461-89-2)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-63-25
• Safety Statements: 26-36-45-38-36/37/39
• WGK Germany: 3
• RTECS: XY7700000
• F: 10-23
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 461-89-2(Hazardous Substances Data)

Usage

Description

6-Azauracil, also known as 6-AU, is a synthetic nucleoside analog that exhibits antimicrobial properties. It is structurally similar to uracil, a pyrimidine base found in RNA, and can be incorporated into RNA during transcription. This incorporation leads to the depletion of intracellular guanosine triphosphate (GTP) and uridine triphosphate (UTP) nucleotide pools, which in turn inhibits the growth of various microorganisms. Due to its unique mechanism of action, 6-Azauracil has been extensively studied for its potential applications in different fields.

Uses

Used in Antimicrobial Applications:
6-Azauracil is used as a growth inhibitor for various microorganisms, such as bacteria and fungi, due to its ability to deplete intracellular GTP and UTP nucleotide pools. This makes it a valuable tool in controlling the growth of harmful microorganisms and preventing infections.
Used in Research and Development:
6-Azauracil has been widely used in investigations on the modulation of transcription, particularly in yeast models. Its incorporation into RNA during transcription allows researchers to study the effects of nucleotide pool depletion on gene expression and regulation. This has led to a better understanding of the molecular mechanisms underlying transcription and the development of potential therapeutic agents targeting these processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-Azauracil is used as a starting material for the synthesis of other nucleoside analogs with potential therapeutic applications. Its unique properties and ability to modulate transcription make it a valuable compound for the development of new drugs targeting various diseases, including cancer and viral infections.

Synthesis Reference(s)

The Journal of Organic Chemistry, 23, p. 1522, 1958 DOI: 10.1021/jo01104a033

Biochem/physiol Actions

6-Azauracil (6-AU) is a pyrimidine analog of uracil and exhibits antitumor activity. It inhibits the growth of various microorganisms by depleting intracellular guanosine triphosphate (GTP)?and uridine?triphosphate (UTP) nucleotide pools.

Safety Profile

Poison by intraperitoneal route. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Mode of action

6-Azauracil is a growth inhibitor effective on a variety of microorganisms. It functions by depleting the intracellular GTP and UTP nucleotide supply. Mutations in transcriptional elongation machinery, as well as mutations in a variety of other pathways, exaggerate the growth defect of cells in the presence of 6 AU.

InChI:InChI=1/C3H5N3O2/c7-2-1-4-6-3(8)5-2/h4H,1H2,(H2,5,6,7,8)

Upstream product

• 18802-37-4 6-aza-5,6-dihydrouracil 
• 626-08-4 6-aza-2-thiouracil 
• 13924-15-7 3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid 
• 928-73-4 glyoxylic acid semicarbazone 

Downstream Products

• 59631-75-3 3,5-dichloro-1,2,4-triazine 
• 18802-37-4 6-aza-5,6-dihydrouracil 
• 1627-37-8 6-aza-4-thiouracil 
• 461-90-5 3,5-dithioxo-2,3,4,5-tetrahydrotriazine 
• 4956-05-2 6-bromo-1,2,4-triazine-3,5(2H,4H)-dione 
• 54-25-1 6-Azauridine 
• 101760-68-3 5-(phenylselenenyl)-6-azauracil 
• 17331-61-2 3,5-bis(trimethylsilyloxy)-1,2,4-triazine 
• 622379-83-3 C₃₀H₂₅N₃O₉ 
• 120-89-8 parabanic acid 
• 61466-03-3 5-methyl-4-[(5-methyl-3-oxo-2-phenyl-2,4-dihydro-3H-pyrazol-4-yl)methylene]-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 
• 195524-88-0 2-(2,5-difluoro-4-cyano-phenyl)-1,2,4-triazine-3,5(2H,4H)-dione 
• 206269-47-8 1-(2',3',5'-tri-O-benzoyl-β-L-ribofuranosyl)-6-azauracil 
• 15677-10-8 6-azido-1,3-dimethyluracil 

Relevant articles and documents

Synthesis of novel 3-substituted-5H-benzo[5,6][1, 4]thiazino[3,2-e][1,2,4]triazines and their 15-lipoxygenase inhibitory activity

A new group of 3-substituted-5H-benzo[5,6][1,4]thiazino[3,2-e][1,2,4]triazines was designed, synthesized and evaluated as inhibitors of 15-lipoxygenase (15-LO), and the results were compared with those of standard ligand 4-methyl-2-(4-methylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine (4-MMPB). Among the newly designed ligands, compound 9e showed the best IC50 of 15-LO inhibition (IC50?=?38?μM). The docking calculations were performed in MOE software based on the function of force-field scoring, in order to study the interaction of these new compounds and standard ligand with 15-LO. The docking study implied that these ligands have hydrogen bond interaction with the residue of active site of 15-LO.

An improved synthesis of the 5-HT1A receptor agonist Eptapirone free base

Eptapirone free base, F11440,4-methyl-2-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)-1,2,4-triazine-3,5(2H,4H)-dione, represents a potent and selective 5-HT1A receptor agonist with high efficacy and the potential to regulate anxiety disorders. Herein, we report a method to retro-synthesize eptapirone free base. The compound consists of heterocyclic aromatic portion and aliphatic portion, and the synthetic route consisted of a total of nine steps with an overall yield of 8.8% starting from the commercially available materials. The key steps in the synthetic method involved: (1) using sodium hydroxide and ethylene glycol as solvent resulted in a better cyclization and yield (61.6%) of 1,2,4-triazine-3,5(2H,4H)-dione; (2) an acceptable yield (63.1%) of 4-tert-butyl(pyrimidin-2-yl)piperazine-1-carboxylate was obtained under an optimized conditions of using triethylamine as a base, ethanol as a solvent, and a reaction temperature of 50?°C for 16?h with non-metal catalysis and less byproducts; (3) the reaction step of eptapirone could get a better yield (49.6%) with an optimized condition of potassium carbonate as a base, acetonitrile as a solvent, NaI as a catalyst, and a reaction temperature of 50?°C for 12?h by nucleophilic substitution reaction. The main advantages of this route were an acceptable product purity, the commercial availability of all starting materials and the absence of high temperature, high pressure and noble metal catalysts, which could result in more feasible commercial applications.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.