27826-76-2

Basic information

• Product Name: N(4)-methyl-5-azacytidine
• Synonyms: N(4)-methyl-5-azacytidine
• CAS NO: 27826-76-2
• Molecular Formula: C9H14N4O5
• Molecular Weight: 258.233
• Mol File: 27826-76-2.mol

Chemical Properties

• Boiling Point: 491.4°Cat760mmHg
• Flash Point: 251°C
• Appearance: /
• Density: 1.84g/cm³
• Vapor Pressure: 1.02E-11mmHg at 25°C
• Refractive Index: 1.741
• PKA: 13.46±0.70(Predicted)
• CAS DataBase Reference: N(4)-methyl-5-azacytidine(CAS DataBase Reference)
• NIST Chemistry Reference: N(4)-methyl-5-azacytidine(27826-76-2)
• EPA Substance Registry System: N(4)-methyl-5-azacytidine(27826-76-2)

Safety Data

• Hazardous Substances Data: 27826-76-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H14N4O5/c1-10-8-11-3-13(9(17)12-8)7-6(16)5(15)4(2-14)18-7/h3-7,14-16H,2H2,1H3,(H,10,12,17)/t4-,5-,6-,7-/m1/s1

Upstream product

• 211695-85-1 N⁴-Methyl-2',3',5'-tri-O-benzoyl-β-D-5-azacytidine 
• 53767-26-3 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methylsulfanyl-1,3,5-triazine-2(1H)-one 
• 53767-25-2 4-Methoxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)one 
• 5991-01-5 2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride 
• 21823-89-2 2,3,5-tri-O-benzoyl-β-D-ribosyl isocyanate 
• 27826-75-1 4-methoxy-1-β-D-ribofuranosyl-1H-[1,3,5]triazin-2-one 
• 74-89-5 methylamine 

Relevant articles and documents

Synthesis and biological activity of N4-methyl-5-azacytidines

Protected N4-methyl and N4,N4-dimethyl derivatives of 5-azacytidine 3 and 4 were prepared by selective aminolysis of benzoylated 4-methoxy-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one 5, by glycosylation of silylated N4-methyl-or N4,N4-dimethyl-5-azacytosines 7 and 8 with 2,3,5-tri-O-benzoyl-α,β-D-ribofuranosyl chloride (11) or by several modifications of the isocyanate method. By the isocyanate approach, also the α-D anomer of protected N4-methyl-5-azacytidine 17 was obtained as a minor product. The protected dimethyl derivative 4 was also obtained by the reaction of isobiuret 22 with dimethylformamide dimethyl acetal. The free nucleosides 1 and 2 were obtained either by aminolysis of the free methoxy nucleoside 23 with methylamine or dimethylamine, respectively, or by methanolysis or ammonolysis of the corresponding benzoyl derivatives 3 and 4. The free α-D anomer 24 was obtained by methanolysis of its tribenzoate 17. Nucleosides 1 and 2 exhibited a lower antibacterial, antitumor and antiviral activity than the unsubstituted 5-azacytidine.