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Synthesis of 1-(2'-O-Methyl-ß -D-Ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dion: an Attractive Building Block for Antisense and Triple-helical Applications
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1  Laboratory for Drug Design and Synthesis Department of Chemistry & Biochemistry University of Maryland, Baltimore County 1000 Hilltop Circle, Baltimore, Maryland 21250, USA

Abstract: Synthesis of the title compound,1-(2'-O-methyl-ß-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine- -4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from Methyl 1-(ß-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative 5. The silyl deprotection of the latter (to form 6), followed by treatment with hydrazine afforded the target nucleoside 1. The reported nucleoside has potentially beneficial applications in biomedicine based on antisense and triple-helical nucleic acid technologies.
Keywords: Synthesis, Nucleoside Analogue, Imidazo[4,5-d]pyridazine, 2'-O-Methyl Nucleoside