2',3',5'-Triacetyl-5-azacytidine

• CAS: 10302-78-0
• Catalog Number: ACM10302780
• Category: Main Products
• Molecular Weight: 370.31
• Molecular Formula: C₁₄H₁₈N₄O₈
• Synonyms: NSC291930, CID324936, 1,3,5-Triazin-2(1H)-one, 4-amino-1-(2,3,5-tri-O-acetyl-.beta.-D-ribofuranosyl)-, s-Triazin-2(1H)-one, 4-amino-1-.beta.-D-ribofuranosyl-, triacetate (ester), 10302-78-0
• IUPAC Name: [3,4-diacetyloxy-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)oxolan-2-yl]methyl acetate
• InChI Key: OTQJVHISAFFLMA-UHFFFAOYSA-N
• Boiling Point: 497.3ºC at 760mmHg
• Flash Point: 254.6ºC
• Density: 1.6g/cm³
• Exact Mass: 370.11200
• H-Bond Acceptor: 10
• H-Bond Donor: 1

Case Study

2',3',5'-Triacetyl-5-Azacytidine as A Potential Prodrug of Azacitidine

Ziemba A, et al. Chemotherapy research and practice, 2011, 2011.

Myelodysplastic syndromes (MDS) are a group of incurable stem cell malignancies that are primarily treated with supportive care. Azacitidine and decitabine are two FDA-approved DNA methyltransferase (DNMT) inhibitors that improve overall response. The study evaluated 2,3,5-triacetyl-5-azacytidine (TAC) as a potential prodrug of azacitidine. The prodrug exhibits significant pharmacokinetic improvements in bioavailability, solubility, and stability compared to the parent compound.
Synthesis of 2,3,5-Triacetyl-5-Azacytidine
· 2 ,3 ,5-triacetyl-5-azacytidine was prepared through condensation of trimethylsilylated-5-azacytosine and 1,2,3,5-tetra-O-acetyl-β-Dribofuranose.
· In a 150 mL, 3-necked flask, a mixture of 5-azacytosine, hexamethyldisilazane, and ammonium sulfate was heated at reflux for 2 hours. A fresh amount of ammonium sulfate was added, and the reflux was continued for 6 hours.
· The excess hexamethyldisilazane was removed under reduced vacuum to afford trimethylsilylated 5- azacytosine as an off-white residue.
· Trimethylsilylated 5-azacytosine and 1,2,3,5-Tetra-Oacetyl-β-D-ribofuranose were dissolved in acetonitrile, and the mixture was cooled at 0◦C in an ice-water bath.
· Trimethylsilyl trifluoromethanesulfonate (TMSOTf) was added slowly at 0°C then stirred at room temperature for 3 hours. The reaction mixture was extracted, washed, dried and recrystallized to obtain the final product.

Custom Reviews

August 12, 2023

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An analytical standard
I am glad that I can buy high-purity 2',3',5'-triacetyl-5-azacytidine on this platform.

Custom Q&A

What's boiling point of 2',3',5'-triacetyl-5-azacytidine ?

497.3±55.0 °C

What is the density of 2',3',5'-triacetyl-5-azacytidine ?

1.60±0.1 g/cm3

How soluble is 2',3',5'-triacetyl-5-azacytidine ?

Solubility of 2',3',5'-Triacetyl-5-azacytidine in ethanol ≤ 30 mg/mL; in dimethyl sulfoxide ≤ 30 mg/mL; in dimethylformamide ≤ 30 mg/mL

What is the acidity factor of 2',3',5'-triacetyl-5-azacytidine ?

3.06±0.20

What is the form of 2',3',5'-triacetyl-5-azacytidine ?

Crystalline solid

What is the method of preparation of 2',3',5'-triacetyl-5-azacytidine ?

Triacetyl-Azacitidine is usually synthesized by the following steps: first, Azacitidine (Adenosine) and Acetic Anhydride (Acetic Anhydride) are reacted under appropriate reaction conditions, which allows the esterification group (Acetyl Group) in the Acetic Anhydride to undergo a substitution reaction with the hydrogen atoms in Azacitidine. At the end of the reaction, a crystallization process is usually performed to obtain a higher purity triacetyl-azacitidine through crystallization and purification steps.

What are the relevant applications of 2',3',5'-triacetyl-5-azacytidine ?

Triacetyl-Azacitidine has a number of potential applications in biomedical research and drug development: ① It can be used as a chemically reactive organic compound for the construction of more complex organic molecules. ② As a stimulating substance, it is used to activate cells and to study aspects such as cell signaling and cell function. ③ For pharmaceutical research, it can be used for pharmacological studies, drug screening and drug development to find new drug candidates for the treatment of diseases. ④ Triacetyl-azacitidine is also used as a probe in cell biology and molecular biology studies to investigate aspects of metabolic pathways, signaling, and biological functions within cells.

What are the storage conditions for 2',3',5'-triacetyl-5-azacytidine ?

2',3',5'-Triacetyl-5-azacytidine should be stored in a dark environment at 2-8°C filled with inert gas.

What is the InChIKey of 2',3',5'-triacetyl-5-azacytidine ?

OTQJVHISAFFLMA-DDHJBXDOSA-N

What is the SMILES of 2',3',5'-triacetyl-5-azacytidine ?

CC(=O)OCC1C(C(C(O1)N2C=NC(=NC2=O)N)OC(=O)C)OC(=O)C

Synthetic Use

Upstream Synthesis Route 1

• 52523-35-0
• 13035-61-5

• 10302-78-0

Reference: [1] Patent: WO2012/135405, 2012, A1, . Location in patent: Page/Page column 64-67

Upstream Synthesis Route 2

• 13035-61-5

• 10302-78-0

Reference: [1] Asian Journal of Chemistry, 2018, vol. 30, # 7, p. 1521 - 1524

Upstream Synthesis Route 3

• 40554-98-1
• 52523-35-0

• 10302-78-0

Reference: [1]Patent: WO2010/17374,2010,A1 .Location in patent: Page/Page column 17-18

Downstream Synthesis Route 1

• 10302-78-0

• 320-67-2

Reference: [1] Patent: WO2010/17374, 2010, A1, . Location in patent: Page/Page column 18

Downstream Synthesis Route 2

• 10302-78-0

• 320-67-2

Reference: [1]Patent: CN110642901,2020,A .Location in patent: Paragraph 0044-0046

* For details of the synthesis route, please refer to the original source to ensure accuracy.