Synthesis and biological activity of 2'-deoxy-6-methyl-5-azacytidine and its alpha-D-anomer.
The stannic chloride catalyzed glycosylation of bis-tri-methylsilyl-6-methyl-5-azacytosine 2 with the halogenose 3 leading to the protected anomeric nucleosides 4a and 4b was investigated. Methanolysis of 4a and 4b afforded the corresponding free nucleosides 1a and 1b. Compounds 4a and 4b were also prepared by the isocyanate method via acetylamidinourea derivatives 6. Antileukemic activity in vitro and inhibition of growth of E. coli by the title compounds are reported.
D000818:Animals; D001374:Azacitidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use; D004353:Drug Evaluation, Preclinical; D004926:Escherichia coli / Q000187:drug effects; D007202:Indicators and Reagents; D009374:Neoplasms, Experimental / Q000188:drug therapy
D007202:Indicators and Reagents; C032450:2'-deoxy-6-methyl-5-azacytidine; D001374:Azacitidine