65134-53-4Relevant academic research and scientific papers
9-(β-D-Ribofurandsyl)purine-6-carboxamide and related compounds
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, (2008/06/13)
Certain 9-(β-D-Ribofuranosyl)purine-6-carboxamide and other related compounds are prepared and are useful as antiviral agents.
Synthesis and Antiviral Activity of Certain 9-β-D-Ribofuranosylpurine-6-carboxamides
Westover, James D.,Revankar, Ganapathi R.,Robins, Roland K.,Madsen, Randall D.,Ogden, John R.,et al.
, p. 941 - 946 (2007/10/02)
To examine the structural parameters necessary for antiviral efficacy of certain purine nucleosides, several 9-β-D-ribofuranosylpurine-6-carboxamides have been synthesized.Glycosylation of the Me3Si derivative of purine-6-carboxamide with protected ribofuranose in the presence of a Lewis acid gave the blocked nucleoside which on deprotection furnished 9-β-D-ribofuranosylpurine-6-carboxamide (6a).Alternatively, 6a was synthesized via the nucleophilic displacement of 9-β-D-ribofuranosyl-6-iodopurine with cyanide ion.Certain 2-amino- and 2-methyl-9-β-D-ribofuranosylpurine-6-carboxamides have also been prepared. 8-Carbamoylguanosine (16) has been prepared by homolytic acylation of the parent nucleoside.These compounds were tested against several RNA and DNA viruses in cell culture. 9-β-D-Ribofuranosylpurine-6-carboxamide (6a), the corresponding 6-thiocarboxamide (7b), and 4-amino-8-(β-D-ribofuranosylamino)pyrimidopyrimidine (8) showed significant in vitro antiviral activity at nontoxic dosage levels. 6a employed in the treatment of Rift Valley fever virus infected mice at 50 (mg/kg)/day gave a 55percent survival rate on day 21 compared to a 30percent survival in the controls.
