6-Azauridine

Base Information

• Chemical Name: 6-Azauridine
• CAS No.: 54-25-1
• Deprecated CAS: 39455-15-7
• Molecular Formula: C8H11 N3 O6
• Molecular Weight: 245.192
• Hs Code.: 29349990
• European Community (EC) Number: 200-199-6
• UNII: 7BVB29RCPR
• DSSTox Substance ID: DTXSID20960091
• Nikkaji Number: J2.311F
• Wikidata: Q27116561
• NCI Thesaurus Code: C291
• Metabolomics Workbench ID: 55187
• ChEMBL ID: CHEMBL564201
• Mol file: 54-25-1.mol

Synonyms:2-beta-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione;6 Azauridine;6-Azauridine;Azauridine

Chemical Property of 6-Azauridine

Chemical Property:

• Melting Point: 157-159 °C(lit.)
• Refractive Index: 1.7950 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 6.70(at 25℃)
• Flash Point: °C
• PSA: 137.67000
• Density: 2.08 g/cm³
• LogP: -3.45690
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated), Pyridine (Slightly), Water
• Water Solubility.: It is soluble in water.
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 245.06478508
• Heavy Atom Count: 17
• Complexity: 372

Purity/Quality:

99% ^*data from raw suppliers

6-Azauridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36

MSDS Files:

Useful:

• Canonical SMILES: C1=NN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: C1=NN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• Uses: Research on cell formation and cancer. 6-Azauridine can be applied in antiviral studies. 6-azauridine inhibits de novo pyrimidine synthesis and DNA synthesis and is converted intracellularly into mono, di, and triphosphate derivatives, which incorporate into RNA and inhibit protein synthesis. It is also used as an antineoplastic antimetabolite. It interferes with pyrimidine biosynthesis thereby preventing formation of cellular nucleic acids. As the triacetate, it is also effective as an antipsoriatic. 6-Azauridine (AzUrd) blocks the conversion of orotic acid into UMP and it is used in antiviral studies.

Technology Process of 6-Azauridine

There total 6 articles about 6-Azauridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2',3',5'-tri-O-acetyl-6-azauridine (2169-64-4) → 6-Azauridine (54-25-1)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 0.25h;

DOI:10.1080/07328319608002030

Reference yield: 89.0%

6-azauridine 2',3'-O-carbonate (59967-97-4) → 6-Azauridine (54-25-1)

Guidance literature:

In pyridine; water; at 100 ℃; for 0.75h;

Reference yield:

6-azauracil (461-89-2) → 6-Azauridine (54-25-1)

Guidance literature:

With Escherichia coli;

upstream raw materials:

6-azauracil

6-azauridine 2',3'-O-carbonate

2',3',5'-tri-O-acetyl-6-azauridine

Downstream raw materials:

2',3',5'-tri-O-acetyl-6-azauridine

6-aza-uridine 5'-monophosphate

5-O-tosyl-2',3'-O-ethoxymethylidene-6-azauridine

6-azacytidine

Refernces

• 1、 Riley,Mummert,Zhou,Schowen,Vander Velde,Morton,Slavik. "Hydrolysis of the prodrug, 2',3',5'-triacetyl-6-azauridine". . p. 1361 - 1370. Retrieved 2007/10/03.