3690-10-6

Basic information

• Product Name: ZEBULARINE
• Synonyms: 1-(β-d-ribofuranosyl)-1,2-dihydropyrimidin-2-one;pyrimidin-2-one beta-ribofuranoside;1--D-Ribofuranosyl-2(1H)-pyrimidinone;4-Deoxyuridine;NSC 309132;Pyrimidin-2-one -D-Ribofuranoside;1-(β-D-Ribofuranosyl)-1,2-dihydropyrimidin-2-one, 2-Pyrimidone-1-β-D-riboside;2(1H)-PyriMidinone, 1-b-D-ribofuranosyl-
• CAS NO: 3690-10-6
• Molecular Formula: C₉H₁₂N₂O₅
• Molecular Weight: 228.203
• EINECS: 2017-001-1
• Product Categories: Carbohydrates & Derivatives;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 3690-10-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 160-162?C
• Boiling Point: 499 °C at 760 mmHg
• Flash Point: 255.6 °C
• Appearance: /solid
• Density: 1.73 g/cm³
• Vapor Pressure: 4.75E-12mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: 2-8°C
• Solubility: DMSO: 16 mg/mL, soluble
• PKA: 13.48±0.70(Predicted)
• 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.
• CAS DataBase Reference: ZEBULARINE(CAS DataBase Reference)
• NIST Chemistry Reference: ZEBULARINE(3690-10-6)
• EPA Substance Registry System: ZEBULARINE(3690-10-6)

Safety Data

• WGK Germany: 3
• RTECS: UW7539720
• Hazardous Substances Data: 3690-10-6(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 3690-10-6 differently. You can refer to the following data:
1. It is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent.
2. It is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent

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.

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-/m1/s1

Upstream product

• 52523-24-7 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 63500-40-3 2',3',5'-tri-O-acetyl-zebularine 
• 557-01-7 Pyrimidin-2(1H)-one 
• 50-69-1 D-ribose 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 

Downstream Products

• 557-01-7 Pyrimidin-2(1H)-one 
• 50-69-1 D-ribose 
• 155831-90-6 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 170660-44-3 2-pyrimidinone-1-β-D-(2'-O-t-butyldimethylsilyl-5'-O-dimethoxytritylriboside) 
• 170660-47-6 2-pyrimidinone-1-β-D-(5'-O-dimethoxytritylriboside) 

Relevant articles and documents

MUTUAL PRODRUG COMPRISING SHORT CHAIN FATTY ACIDS AND ZEBULARINE OR 1'-CYANO-CYTARABINE FOR CANCER TREATMENT

The present invention provides mutual prodrugs comprising anti-cancer nucleosides and short chain fatty acids; methods for production of the mutual prodrugs; methods of treatment comprising administration of the mutual prodrugs; and pharmaceutical composi

Formation of a β-pyrimidine nucleoside by a free pyrimidine base and ribose in a plausible prebiotic reaction

The problem of β-nucleoside formation under prebiotic conditions represents one of the most significant challenges to the RNA world hypothesis and to many of its proposed precursors. The possibility exists that alternative bases may have come before the contemporary bases (i.e., A, G, C, and U), including bases that more readily form nucleosides. In a search for pyrimidine bases that are able to form nucleosides in plausible prebiotic reactions, it was discovered that the drying and heating of 2-pyrimidinone with ribose produces a β-furanosyl ribonucleoside in approximately 12% yield. At least two other chemical isomers of zebularine are also produced in the condensation reaction. This work represents the first successful synthesis of a pyrimidine nucleoside from a free base and a nonactivated sugar in a plausible prebiotic reaction. A comparison of 2-pyrimidinone with the purine bases that have also been demonstrated to form nucleosides in plausible prebiotic reactions provides insights regarding what chemical features of the bases facilitate glycoside formation in drying-heating reactions. Copyright

A New Synthesis of 3-(β-D-Ribofuranosyl)uracil (Isouridine) via the Intermediacy of a O6,5'-Cyclotetrahydropyrimidinone Nucleoside

A specific and efficient synthesis for 3-(β-D-ribofuranosyl)uracil, isouridine (1), has been devised.Starting with the easily accessible 1-(β-D-ribofuranosyl)-1,2-dihydropyrimidin-2-one (3b) the C-6 carbonyl function of isouridine was built via formation