Zebularine

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Names

[ CAS No. ]:
3690-10-6

[ Name ]:
Zebularine

[Synonym ]:
4-Deoxyuridine
1--D-Ribofuranosyl-2(1H)-pyrimidinone
4-Deoyuridine
2(1H)-PyriMidinone,1-b-D-ribofuranosyl
1-(β-D-Ribofuranosyl)pyrimidin-2(1H)-one
2(1H)-Pyrimidinone, 1-β-D-ribofuranosyl-
Pyrimidin-2-one b-Ribofuranoside
Zebularine
[14C]-Zebularine
1-b-D-Ribofuranosyl-2(1H)-pyrimidinone
2(1H)-Pyrimidinone, 1-.β.-D-ribofuranosyl-
Pyrimidin-2-one-D-Ribofuranoside
1-(β-D-Ribofuranosyl)-2(1H)-pyrimidinone

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
499.0±55.0 °C at 760 mmHg

[ Melting Point ]:
160-162?C

[ Molecular Formula ]:
C9H12N2O5

[ Molecular Weight ]:
228.202

[ Flash Point ]:
255.6±31.5 °C

[ Exact Mass ]:
228.074615

[ PSA ]:
104.81000

[ LogP ]:
-1.31

[ Appearance of Characters ]:
solid

[ Vapour Pressure ]:
0.0±2.9 mmHg at 25°C

[ Index of Refraction ]:
1.697

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: 16 mg/mL, soluble

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UW7539720

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2-dihydropyrimidin-2-one
  • pyrimidone
  • D-Ribose
  • [3,4-diacetyloxy-5-(2-oxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
  • b-D-Ribofuranose 1-acetate 2,3,5-tribenzoate
  • Beta-D-Ribofuranose 1,2,3,5-tetraacetate

DownStream

  • pyrimidone
  • D-Ribose

Articles

The potential of clofarabine in MLL-rearranged infant acute lymphoblastic leukaemia.

Eur. J. Cancer 51 , 2008-21, (2015)

MLL-rearranged acute lymphoblastic leukaemia (ALL) in infants is the most difficult-to-treat type of childhood ALL, displaying a chemotherapy-resistant phenotype, and unique histone modifications, gen...

DNA Methylation Inhibitor Zebularine Confers Stroke Protection in Ischemic Rats.

Transl. Stroke Res. 6 , 296-300, (2015)

5-Aza-deoxycytidine (5-aza-dC) confers neuroprotection in ischemic mice by inhibiting DNA methylation. Zebularine is another DNA methylation inhibitor, less toxic and more stable in aqueous solutions ...

Light signaling controls nuclear architecture reorganization during seedling establishment.

Proc. Natl. Acad. Sci. U. S. A. 112 , E2836-44, (2015)

The spatial organization of chromatin can be subject to extensive remodeling in plant somatic cells in response to developmental and environmental signals. However, the mechanisms controlling these dy...


More Articles

Related Compounds

  • zebularine cep
  • [2-14C]zebularine
  • zebularine-5'-monophosphate
  • 2',3',5'-tri-O-acetyl-zebularine
  • (4-Morpholinophenyl)(5-phenylthiophen-3-yl)methanone
  • tert-Butyl 5-methyl-1,2,3-oxathiazinane-3-carboxylate 2,2-dioxide
  • 3-(4-Formyl-1H-pyrazol-1-yl)-5-methylhexanenitrile
  • 5-amino-2'-morpholino-[3,4'-bipyridin]-2(1H)-one
  • 3-[3-(4-chloro-3,5-dimethylphenoxy)propyl]-7-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-indole-2-carboxylic acid
  • 1-(3-Bromo-5-chloropyridin-4-yl)-4-(hydroxymethyl)piperidine-4-carbonitrile
  • tert-butyl (5S)-2-oxo-5-(trifluoromethyl)pyrrolidine-1-carboxylate
  • 8-(3-Bromo-5-chloro-4-pyridinyl)-2,8-diazaspiro[4.5]decane-1,4-dione
  • 1-(3-Bromo-5-chloropyridin-4-yl)-4-(methoxymethyl)piperidine-4-carbonitrile
  • 1-(3-Bromo-5-chloropyridin-4-yl)-4-(2-hydroxyethyl)piperidine-4-carbonitrile
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