Zebularine

Source: Wikipedia, the free encyclopedia.
Zebularine
Names
IUPAC name
1-(β-D-Ribofuranosyl)pyrimidin-2(1H)-one
Systematic IUPAC name
1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2(1H)-one
Other names
Pyrimidin-2-one β-D-ribofuranoside
Identifiers
3D model (
JSmol
)
ChemSpider
IUPHAR/BPS
UNII
  • InChI=1S/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-/m1/s1
    Key: RPQZTTQVRYEKCR-WCTZXXKLSA-N
  • 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-/m1/s1
    Key: RPQZTTQVRYEKCR-WCTZXXKLBP
  • O=C1/N=C\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
Properties
C9H12N2O5
Molar mass 228.204 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Zebularine is a

nucleoside analog of cytidine. It is a transition state analog inhibitor of cytidine deaminase by binding to the active site as covalent hydrates. Also shown to inhibit DNA methylation and tumor growth both in vitro and in vivo.[1]

In a small study of mice with a defective

chemoprevention.[3]

Zebularine (left) closely resembles cytidine (right), but lacks the 4'-amino group.

References

  1. ^ "pyrimidin-2-one beta-ribofuranoside - Compound Summary". PubChem/National Center for Biotechnology Information.
  2. PMID 19138966
    .
  3. PMID 15809275
    .
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