2,2'-Cyclouridine

Names

[ Name ]:
2,2'-Cyclouridine

[Synonym ]:
O2,2'-Cyclouridine
EINECS 223-107-6
2,2'-Cyclouridine
2,2'-O-Cyclouridine
MFCD00004945
2,2-Anhydro-1(b-D-arabinofuranosyl)uracil
2,2'-Anhydro-1(B-D-arabinofuranosyl)uracil
2,2′-O-Cyclouridine
6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one, 2,3,3a,9a-tetrahydro-3-hydroxy-2-(hydroxymethyl)-, (2R,3R,3aS,9aR)-
O2,2'-Cyclouridine (VAN)
(2R,3R,3aS,9aR)-3-Hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-6-one
2,2'-Anhydrouridine

Biological Activity

[Description]:

2,2'-Anhydrouridine is used for anticancer and antiviral research[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Research Areas >> Infection

[References]

[1]. Drabikowska AK, et al. Inhibitor properties of some 5-substituted uracil acyclonucleosides, and 2,2'-anhydrouridines versus uridine phosphorylase from E. coli and mammalian sources. Biochem Pharmacol. 1987 Dec 1;36(23):4125-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Boiling Point ]:
456.3±55.0 °C at 760 mmHg

[ Melting Point ]:
239-240ºC

[ Molecular Formula ]:
C₉H₁₀N₂O₅

[ Molecular Weight ]:
226.186

[ Flash Point ]:
229.8±31.5 °C

[ Exact Mass ]:
226.058975

[ PSA ]:
93.81000

[ LogP ]:
-1.40

[ Vapour Pressure ]:
0.0±2.5 mmHg at 25°C

[ Index of Refraction ]:
1.816

[ Storage condition ]:
Store at RT.

MSDS

Click to get detail MSDS

Safety Information

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

[ Hazard Codes ]:
T+

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
29349990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

2,2'-Anhydro-1-(3',5'-di-O-acetyl-β-D-arabinofuranosyl)uracil, a cyclouridine nucleoside with a C4'-endo furanosyl conformation.

Acta Crystallogr. C 69(Pt 3) , 282-4, (2013)

2,2'-Anhydro-1-(3',5'-di-O-acetyl-β-D-arabinofuranosyl)uracil, C13H14N2O7, was obtained by refluxing 2',3'-O-(methoxymethylene)uridine in acetic anhydride. The structure exhibits a nearly perfect C4'-...

Aldrichimica Acta 20 , 52, (1987)

Inhibitor properties of some 5-substituted uracil acyclonucleosides, and 2,2'-anhydrouridines versus uridine phosphorylase from E. coli and mammalian sources.

Biochem. Pharmacol. 36(23) , 4125-8, (1987)

Two series of 5-substituted uracil N(1)-acyclonucleosides, each with a different acyclic chain, were examined as inhibitors of uridine phosphorylase from rat intestinal mucosa, and several against the...