Synthesis of 1-(2'-O-Methyl-ß-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications

doi:10.3390/60300203

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Molecules 2001, 6(3), 203-207; doi:10.3390/60300203

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Synthesis of 1-(2'-O-Methyl-ß-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications

Huan-Ming Chen and Ramachandra S. Hosmane*

Laboratory for Drug Design and Synthesis, Department of Chemistry & Biochemistry, University of Maryland, Baltimore County (UMBC), 1000 Hilltop Circle, Baltimore, Maryland 21250, USA

* Author to whom correspondence should be addressed.

Received: 12 October 2000; in revised form: 18 January 2001 / Accepted: 19 January 2001 / Published: 28 February 2001

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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 Introduction

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MDPI and ACS Style

Chen, H.-M.; Hosmane, R.S. Synthesis of 1-(2'-O-Methyl-ß-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications. Molecules 2001, 6, 203-207.

AMA Style

Chen H.-M., Hosmane R.S. Synthesis of 1-(2'-O-Methyl-ß-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications. Molecules. 2001; 6(3):203-207.

Chicago/Turabian Style

Chen, Huan-Ming; Hosmane, Ramachandra S. 2001. "Synthesis of 1-(2'-O-Methyl-ß-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications." Molecules 6, no. 3: 203-207.

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