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.
Chemical Properties
WHITE FINE POWDER
Uses
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.
Uses
5-Bromouridine is a uridine (U829910) derivative and is often incorporated into RNA in order to detect immunocytochemically and analyzed by cytometry.
Definition
ChEBI: A uridine having a bromo substituent at the 5-position.
Synthesis
General method: 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (5, 0.103 g, 0.4 mmol) was dissolved in aqueous acetonitrile (H2O:CH3CN = 1:9, 5 mL) under stirring conditions. Subsequently, NaN3 (0.104 g, 1.6 mmol) was added and SMBI (0.101 g, 0.44 mmol) was added at room temperature. The reaction mixture was stirred continuously and the progress of the reaction was monitored by thin layer chromatography (TLC). After 1.5 h of reaction, the reaction mixture was filtered, concentrated under reduced pressure and co-evaporated with acetonitrile (2 × 2 mL) to remove residual water. The crude product was purified by column chromatography (eluent: 4%-6% methanol in dichloromethane, v/v) to afford the pure 5-bromouridine (6, 0.117 g, 93%) as a white solid.
Purification Methods
Recrystallise it from 96% EtOH. UV max 279nm (log 3.95)in 2O pH 1.9. RF in n -BuOH/AcOH/H2O (4:4:1) is 0.49; in n-BuOH/EtOH/H2O (40:11:9) it is 0.46 and in isoPrOH/25%NH3/H2O (7:1:2) it is 0.53 using Whatman No 1 paper. [Pryst.s & Sorm Collect Czech Chem Commmun 29 2956 1964, Beilstein 31 H 24.]
References
[1] Canadian Journal of Chemistry, 1994, vol. 72, # 9, p. 2005 - 2010
[2] Synthesis, 2009, # 23, p. 3957 - 3962
[3] Journal of Organic Chemistry, 1990, vol. 55, # 16, p. 4928 - 4933
[4] Organic and Biomolecular Chemistry, 2008, vol. 6, # 16, p. 2884 - 2891
[5] Nucleosides, Nucleotides and Nucleic Acids, 2009, vol. 28, # 9, p. 821 - 834
