| Identification | Back Directory | [Name]
ZEBULARINE | [CAS]
3690-10-6 | [Synonyms]
NSC 309132
4-Deoyuridine
4-Deoxyuridine
Zebularine Zebularine
NSC309132;4-DEOXYURIDINE
2-Pyrimidone-1-β-D-riboside
Uridine Impurity 23 (Zebularine)
Pyrimidin-2-one -D-Ribofuranoside
pyrimidin-2-one beta-ribofuranoside
1--D-Ribofuranosyl-2(1H)-pyrimidinone
Pyrimidin-2-one beta-D-ribofuranoside
Zebularine - CAS 3690-10-6 - Calbiochem
1-b-D-ribofuranosyl-2-(1H)-pyriMidinone
2(1H)-PyriMidinone, 1-b-D-ribofuranosyl-
2(1H)-Pyrimidinone, 1-β-D-ribofuranosyl-
1-beta-D-Ribofuranosyl-2(1H)-pyrimidinone
anticancer drug, DNA Methylation inhibitor
1-(β-d-ribofuranosyl)-1,2-dihydropyrimidin-2-one
4-Deoyuridine, 1-beta-D-ribofuranosyl-2-(1H)-pyrimidinone
1-(β-D-Ribofuranosyl)-1,2-dihydropyrimidin-2-one, 2-Pyrimidone-1-β-D-riboside | [EINECS(EC#)]
2017-001-1 | [Molecular Formula]
C9H12N2O5 | [MDL Number]
MFCD04973699 | [MOL File]
3690-10-6.mol | [Molecular Weight]
228.203 |
| Chemical Properties | Back Directory | [Melting point ]
160-162?C | [Boiling point ]
499.0±55.0 °C(Predicted) | [density ]
1.73±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
DMSO: 16 mg/mL, soluble
| [form ]
solid
| [pka]
13.48±0.70(Predicted) | [color ]
White | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month. | [InChI]
InChI=1/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/s3 | [InChIKey]
RPQZTTQVRYEKCR-WCTZXXKLSA-N | [SMILES]
N1(C=CC=NC1=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O |&1:7,9,12,14,r| |
| Hazard Information | Back Directory | [Description]
Zebularine (3690-10-6) is an orally active DNA methyltransferase inhibitor. Inhibits tumor cell proliferation (IC50 = 120 μM) and re-activates silenced genes in T24 bladder carcinoma cells. Zebularine inhibits cytidine deaminase (Ki ~ 2 μM and; induces differentiation of mesenchymal stem cells into cardiomyocytes. | [Chemical Properties]
White Solid | [Uses]
It is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent | [Uses]
Zebularine is a DNA methylation inhibitor which acts by forming a covalent complex with DNMT. It displays antiangiogenic activity and markedly inhibits vessel formation in different tumor models. It reactivates silenced E-cadherin and potentiates the effects of other epigenetic therapeutics such as vorinistat. Induces differentiation of mesenchymal cells into cardiomyocytes. Inhibits cytidine deaminase. | [Definition]
ChEBI: Zebularine is a member of pyrimidine ribonucleosides. | [Biological Activity]
Orally active DNA methyltransferase inhibitor. Inhibits tumor cell proliferation (IC 50 = 120 μ M) and re-activates silenced genes in T24 bladder carcinoma cells. Also inhibits cytidine deaminase (K i ~ 2 μ M). | [Biochem/physiol Actions]
Zebularine is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent. | [Synthesis]
The general procedure for the synthesis of 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one from the compound (CAS: 52523-24-7) was as follows: compound 15 (9.5 g, 17.6 mmol) was dissolved in methanol (100 mL) and cooled to 0 °C. To this cooled solution a methanol solution of 7N ammonia (245 mL) was slowly added. The reaction mixture was stirred at 25°C for 24 hours. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure. The residue was diluted with water and extracted with chloroform. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 10:1) to afford compound 16 (3.8 g, 94% yield) as a white solid. Its 1H NMR (400 MHz, methanol-d4) data were as follows: δ 8.79 (dd, J = 6.8, 2.8 Hz, 1H), 8.57 (dd, J = 4.0, 2.8 Hz, 1H), 6.58 (dd, J = 6.8, 4.4 Hz, 1H), 5.86 (s, 1H), 4.15-4.10 (m, 3H), 3.98 ( dd, J = 12.4, 2.0 Hz, 1H), 3.79 (dd, J = 12.8, 2.0 Hz, 1H). | [storage]
Desiccate at RT | [References]
[1] Patent: WO2015/72784, 2015, A1. Location in patent: Page/Page column 21; 22
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 1, p. 127 - 130
[3] Tetrahedron Letters, 1994, vol. 35, # 10, p. 1597 - 1600
[4] Journal of Medicinal Chemistry, 1981, vol. 24, # 6, p. 662 - 666 |
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