CAS 10302-78-0

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

Description:

2',3',5'-Triacetyl-azacytidine is a modified nucleoside that features an azole ring, specifically a pyrimidine derivative, with three acetyl groups attached to the hydroxyl groups at the 2', 3', and 5' positions of the ribose moiety. This compound is characterized by its ability to mimic natural nucleosides, which makes it of interest in biochemical and pharmaceutical research, particularly in the study of nucleic acid interactions and the development of antiviral agents. The acetyl groups enhance the lipophilicity of the molecule, potentially influencing its cellular uptake and biological activity. Additionally, the presence of the nitrogen atom in the azacytidine structure can affect hydrogen bonding and base pairing properties, making it a valuable tool in the exploration of RNA and DNA processes. Its stability, solubility, and reactivity can vary depending on environmental conditions, which is crucial for its applications in synthetic biology and medicinal chemistry. Overall, 2',3',5'-Triacetyl-azacytidine serves as an important compound for understanding nucleoside function and developing therapeutic agents.

Formula: C₁₄H₁₈N₄O₈

InChI: InChI=1/C14H18N4O8/c1-6(19)23-4-9-10(24-7(2)20)11(25-8(3)21)12(26-9)18-5-16-13(15)17-14(18)22/h5,9-12H,4H2,1-3H3,(H2,15,17,22)

InChI key: OTQJVHISAFFLMA-DDHJBXDOSA-N

SMILES: CC(=O)OCC1C(C(C(n2cnc(=N)nc2O)O1)OC(=O)C)OC(=O)C

Synonyms:

• 4-amino-1-(2,3,5-tri-O-acetylpentofuranosyl)-1,3,5-triazin-2(1H)-one
• 1,3,5-Triazin-2(1H)-one, 4-amino-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)-
• 2',3',5'-triacetyl-5-Azacytosine
• 2'',3'',5''-Triacetyl -Azacytidine
• 1,3,5-Triazin-2(1H)-one, 4-amino-1-(2,3,5-tri-o-acetyl-.beta.-D-ribofuranosyl)-
• Nsc291930
• S-Triazin-2(1H)-one, 4-amino-1-.beta.-D-ribofuranosyl-, triacetate (ester)
• (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(4-amino-2-oxo-1,3,5-triazin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
• 2',3',5'-triacetyl-5-Azacytidine

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

CAS: 10302-78-0

Formula: C₁₄H₁₈N₄O₈

Purity: 97%

Color and Shape: Solid

Molecular weight: 370.3147

Ref: IN-DA007IB6

2',3',5'-triacetyl-5-Azacytidine

CAS: 10302-78-0

2',3',5'-triacetyl-5-Azacytidine

Formula: C₁₄H₁₈N₄O₈

Purity: ≥98%

Molecular weight: 370.31

Ref: 54-BUP12983

Azacitidine Triacetate

CAS: 10302-78-0

Formula: C₁₄H₁₈N₄O₈

Color and Shape: White To Off-White Solid

Molecular weight: 370.32

Ref: 4Z-A-8132

2',3',5'-Tri-O-acetyl-5-azacytidine

CAS: 10302-78-0

Color and Shape: Neat

Ref: 86-MM1259.20

2',3',5'-triacetyl-5-Azacytidine

CAS: 10302-78-0

2',3',5'-triacetyl-5-Azacytidine (Nsc291930) is a prodrug form of 5-azacytidine that may be rapidly absorbed orally.

Formula: C₁₄H₁₈N₄O₈

Purity: 98.34%

Color and Shape: White Solid

Molecular weight: 370.315

Ref: TM-T7840

Tri Acetyl Azacitidine

CAS: 10302-78-0

Formula: C₁₄H₁₈N₄O₈

Molecular weight: 370.31

Ref: ST-EA-CP-A35004

2',3',5'-triacetyl-5-Azacytidine

CAS: 10302-78-0

Ref: BE-RMCA339023

2′,3′,5′-Triacetyl-5-azacytidine

CAS: 10302-78-0

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(4-amino-2-oxo-1,3,5-triazin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate

Formula: C₁₄H₁₈N₄O₈

Purity: 97%

Molecular weight: 370.31

Ref: IN-DG571848

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

CAS: 10302-78-0

Formula: C₁₄H₁₈N₄O₈

Purity: 97%

Molecular weight: 370.318

Ref: 10-F493341

5-Azacytidine 2’,3’5’-O-triacetate

CAS: 10302-78-0

Applications 5-Azacytidine 2’,3’5’-O-triacetate is a useful compound for the treatment and prevention of cancer and disorders related to abnormal cell proliferation, hematological disorders, and myelodysplastic syndromes (MDS). It can be also used to synthesize 2'3'5'triacetyl-5-azacytidine which is a prodrug for azacitidine. Azacitidine is a FDA-appproved DNA metnyltransferase (DNMT) inhibitor.
References Rajendiran, C., et al.: PCT Int. Appl. WO 2012135405 A1 20121004 (2012); Ziemba, A., et al.: Chemother Res Pract 965826, 9 (2011); Beisler, J. A., et al.: J. Carbohyd. Chem 4, 281 (1977)

Formula: C₁₄H₁₈N₄O₈

Color and Shape: Neat

Molecular weight: 370.31

Ref: TR-A796030

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

CAS: 10302-78-0

2',3',5'-Triacetyl-azacytidine is a transcription factor that has dose-dependent effects on the production of melanin. It inhibits the synthesis of melanin by binding to two specific transcription factors, the microphthalmia-associated transcription factor and the histone methyltransferases. This drug also inhibits tyrosinase, which is an enzyme involved in the production of melanin. 2',3',5'-Triacetyl-azacytidine has been shown to inhibit the growth of murine melanoma cells and may be useful for treating skin cancer.

Formula: C₁₄H₁₈N₄O₈

Purity: Min. 95%

Molecular weight: 370.31 g/mol

Ref: 3D-NT57363