Brivudine Chemical Properties

Melting point:

165°C

Density 

1.7800 (rough estimate)

refractive index 

1.6520 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

8.37±0.10(Predicted)

color 

Off-White

Water Solubility 

Soluble in water and methanol.

Merck 

14,1378

InChIKey

ODZBBRURCPAEIQ-CXYVBZRVSA-N

Safety Information

Safety Statements 

24/25

WGK Germany 

3

RTECS 

YU7355000

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

Brivudine Usage And Synthesis

Description

(E)-5-(2-Bromovinyl)-2'-deoxyuridine is an thymidine analogue and acts as an anti-viral by inhibiting DNA plymerase.

Chemical Properties

White solid

Uses

It is used as pharmaceutical intermediate.

Uses

Brivudine is a nucloside analog which causes induction of neuronal differentiation in human reporter cell lines and adult stem cells. Anti-Herpes medication.

Synthesis

GENERAL STEPS: To a solution of (E)-5-(2-carboxyvinyl)-1-(2-deoxy-β-D-erythro-pentofuranosyl)pyrimidine-2,4(1H,3H)-dione (5.777 g, 19.37 mmol) in dimethylformamide (29 mL) was added K2CO3 (5.890 g, 42.61 mmol), and the suspension was stirred at room temperature for for 15 min. A solution of N-bromosuccinimide (3.655 g, 20.53 mmol) was added dropwise over a period of 30 min at 20 °C. After completion of the reaction, the resulting suspension was filtered and the solid was washed with DMF. The combined filtrate and washings were evaporated to dryness under vacuum and the residue was dissolved in methanol. Silica gel was added to this solution, the suspension was evaporated to dryness, and the solid was loaded onto the top of the column. Column chromatography using chloroform/methanol (92:8, v/v) as eluent gave a white solid (5.787 g, 71.9% yield). A white powder was obtained by recrystallization from water. The structure of the product was confirmed by 1H-NMR and 13C-NMR: 1H-NMR (DMSO-d6; 300 MHz) δ 11.59 (1H, bs, NH-3), 8.08 (1H, s, H-6), 7.25 (1H, d, 3J = 13.6 Hz, H-5B), 6.85 (1H, d, J = 13.6 Hz, H-5A) , 6.13 (1H, t, 3J = 6.5 Hz, H-1'), 5.29 (1H, bs, OH-3'), 5.13 (1H, bs, OH-5'), 4.24 (1H, m, H-3'), 3.79 (1H, m, H-4'), 3.66 (2H, m, H-5'), 2.51 (1H, m, H-2'), 2.14 (1H, m, H-2'); 13C-NMR (DMSO-d6; 75 MHz) δ 40.2 (C-2'), 61.3 (C-5'), 70.3 (C-4'), 84.8 (C-3'), 87.8 (C-1'), 108.9 (C-5B), 110.0 (C-5), 130.3 (C-5A), 149.6 , 162.1 (c-2, c-4).

in vivo

References

[1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6663 - 6671
[2] RSC Advances, 2015, vol. 5, # 31, p. 24558 - 24563
[3] Patent: WO2005/12327, 2005, A2. Location in patent: Page/Page column 24-25
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5640 - 5642
[5] Patent: US6653318, 2003, B1

Brivudine(69304-47-8)Related Product Information

• VINYL PROPIONATE
• N-Vinyl-2-pyrrolidone
• Brimonidine Tartrate
• Tris(hydroxymethyl)nitromethane
• Doxifluridine
• Brimonidine
• 4-Bromostyrene
• ETHYLENE
• Triethoxyvinylsilane
• 1,2-DIBROMOETHYLENE
• beta-Bromostyrene
• Vinyl bromide
• 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE
• 2-ISOPROPYL-6-METHYL-4-PYRIMIDINOL
• Polyethylene
• CHLOROPHOSPHONAZO III
• Floxuridine
• Styrene