5-Bromouridine

Base Information

• Chemical Name: 5-Bromouridine
• CAS No.: 957-75-5
• Deprecated CAS: 21597-77-3
• Molecular Formula: C9H11BrN2O6
• Molecular Weight: 323.1
• Hs Code.: 29349990
• European Community (EC) Number: 213-486-6
• UNII: KEY8PG1BRC
• DSSTox Substance ID: DTXSID401317210
• Nikkaji Number: J93.350C
• Wikipedia: 5-Bromouridine
• Wikidata: Q4639573
• Metabolomics Workbench ID: 53769
• ChEMBL ID: CHEMBL2206658
• Mol file: 957-75-5.mol

Synonyms:1-D-ribofuranosyl-5-bromouracil-nucleoside;5-bromouridine;bromouridine

Chemical Property of 5-Bromouridine

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 180-182 °C (dec.)(lit.)
• Refractive Index: 1.69
• PKA: 7.73±0.10(Predicted)
• PSA: 124.78000
• Density: 2.043 g/cm³
• LogP: -2.08940
• Storage Temp.: 0-6°C
• Solubility.: Water (Sonicated)
• Water Solubility.: Insoluble in water.
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 321.98005
• Heavy Atom Count: 18
• Complexity: 414

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Bromouridine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)Br
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)Br
• Description: 5-Bromouridine is an energy-related metabolite that is a precursor of uridine. 5-Bromouridine binds to the nuclear DNA in cells, where it can act as a transcriptional regulator. 5-Bromouridine is used in the treatment of malignant brain tumors, where it can inhibit tumor growth by binding to the dna of cancer cells and preventing the synthesis of proteins required for cell division.
• Uses: 5-Bromouridine is a uridine (U829910) derivative and is often incorporated into RNA in order to detect immunocytochemically and analyzed by cytometry. 5-Bromouridine is often incorporated into RNA in order to detect immunocytochemically and analyzed by cytometry. It possesses anti-viral activity and inhibits the activity of viruses such as human immunodeficiency virus.

Technology Process of 5-Bromouridine

There total 19 articles about 5-Bromouridine 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%

uridine (58-96-8) → 5-bromouridine (957-75-5)

Guidance literature:

With N-Bromosuccinimide; sodium azide; In 1,2-dimethoxyethane; water; at 25 ℃; for 24h;

DOI:10.1139/v94-256

Reference yield: 95.0%

araU (3083-77-0) → aBrUra (957-75-5,3266-88-4,3370-69-2,38953-77-4,82950-04-7)

Guidance literature:

With N-Bromosuccinimide; sodium azide; In 1,2-dimethoxyethane; water; at 25 ℃; for 24h;

DOI:10.1139/v94-256

Reference yield: 87.0%

5-bromo-2’,3’,5’-tri-O-acetyluridine (105659-31-2,105659-32-3) → 5-bromouridine (957-75-5)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo00303a033

upstream raw materials:

5-bromocytidine

5-bromo-2’,3’,5’-tri-O-acetyluridine

uridine

Tri-O-acetyluridine

Downstream raw materials:

aBrUra

5-bromouracil

5-iodouridine

2',3',5'-tri-O-benzoyl-5-bromouridine

Refernces

• 1、 Platonova, Yana B.,Tomilova, Larisa G.,Volov, Alexander N.. "The synthesis and antituberculosis activity of 5-alkynyl uracil derivatives". . . Retrieved 2020/06/26.
• 2、 Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias. "Thermodynamic Reaction Control of Nucleoside Phosphorolysis". supporting information. p. 867 - 876. Retrieved 2020/01/24.