| Identification | Back Directory | [Name]
1-(α-D-ribofuranosyl)uracil | [CAS]
3258-07-9 | [Synonyms]
0/9/58
alpha-Uridine
alpha-D-Uridine
1-(a-D-ribofuranosyl)uracil
1-(alpha-D-ribofuranosyl)uracil
2,4(1H,3H)-Pyrimidinedione, 1-α-D-ribofuranosyl-
1-alpha-D-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione
alpha-D-Ribofuranoside, 2,4(1H,3H)-pyrimidinedione-1 | [Molecular Formula]
C9H12N2O6 | [MDL Number]
MFCD17430297 | [MOL File]
3258-07-9.mol | [Molecular Weight]
244.2 |
| Chemical Properties | Back Directory | [density ]
1.674±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
Solid | [pka]
9.39±0.10(Predicted) | [color ]
White to off-white | [InChI]
InChI=1/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8+/s3 | [InChIKey]
DRTQHJPVMGBUCF-WAALHAOGNA-N | [SMILES]
O[C@@H]1[C@@H]([C@@H](CO)O[C@@H]1N1C=CC(=O)NC1=O)O |&1:1,2,3,7,r| |
| Hazard Information | Back Directory | [Uses]
1-(a-D-ribofuranosyl)uracil is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1]. | [Synthesis]
The general procedure for the synthesis of 1-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (Product A) from Compound D (CAS:3258-15-9) was as follows: 98 g of Compound D was dissolved in 500 mL of 0.1N hydrochloric acid solution at 20-25 °C The reaction was stirred at 20-25 °C for 24 h, during which the progress of the reaction was monitored by HPLC until the content of the remaining substance decreased to 0.21%. Upon completion of the reaction, the pH of the reaction system was adjusted to 7-8 using concentrated ammonia, followed by concentration under reduced pressure at 50±5°C until the volume was not reduced. Next, 500 mL of anhydrous acetonitrile was added to the concentrated residue and stirred at 70±5 °C until complete dissolution. Insoluble impurities were removed by filtration and the filtrate was crystallized by stirring at 0±5°C for 12 hours. The white solid product A was collected by filtration and analyzed by HPLC showing a purity of 99.92%. Finally, the product was blown dry at 45 °C for 24 h to give 71.8 g of the target compound. | [References]
[1] Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88. DOI:10.2174/138161212801227005 |
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