97818-28-5

Upstream product

• 124-40-3 dimethyl amine 
• 53767-25-2 4-Methoxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)one 
• 53767-26-3 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methylsulfanyl-1,3,5-triazine-2(1H)-one 
• 122-51-0 orthoformic acid triethyl ester 
• 211695-92-0 C₃₀H₃₀N₄O₈ 
• 5991-01-5 2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride 
• 211695-91-9 Dimethyl-(4-trimethylsilanyloxy-[1,3,5]triazin-2-yl)-amine 
• 16352-15-1 4-dimethylamino-1H-[1,3,5]triazin-2-one 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 27826-77-3 4-dimethylamino-1-β-D-ribofuranosyl-1H-[1,3,5]triazin-2-one 

Relevant academic research and scientific papers

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.