105330-92-5Relevant academic research and scientific papers
Synthesis of some 6-substituted 5-azacytidines
Hanna, Naeem B.,Masojidkova, Milena,Fiedler, Pavel,Piskala, Alois
, p. 222 - 230 (2007/10/03)
Protected 6-substituted benzyl, phenyl and chloromethyl derivatives of 5-azacytidine 8-10 have been prepared by addition of phenylacetyl-(2), benzoyl-(3) or (chloroacetyl)guanidine (4) to 2,3,5-tri-O-benzoyl-β-D-ribosyl isocyanate (1) and subsequent silylation-mediated cyclization of the obtained acyl(carbamoyl)guanidines 5-7. 4-Amino-6-phenyl-1,3,5-triazin-2(1H)-one (12) was obtained by condensation of carbamoylguanidine (13) with methyl benzoate in presence of methanolic sodium methoxide or by condensation of 13 with triethyl orthobenzoate in N,N-dimethylformamide. Stannic chloride catalyzed condensation of silylated 6-phenyl derivative 11 with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribose (14) in 1,2-dichloroethane afforded a 1.2 : 1 mixture of N1 and N3 nucleosides 9 and 15, respectively. Methanolysis of the protected compounds 8-10 and 15 gave the respective free nucleosides 16-19. The latter compounds inhibited the growth of bacteria E. coli B to a much lower extent than the unsubstituted 5-azacytidine.
