Synthesis and antiviral activity of certain 9-beta-D-ribofuranosylpurine-6-carboxamides.

doi:10.1021/JM00140A006

Paper

Synthesis and antiviral activity of certain 9-beta-D-ribofuranosylpurine-6-carboxamides.

Published Aug 1, 1981 · J. D. Westover, G. R. Revankar, R. K. Robins

Journal of medicinal chemistry

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29

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0

Influential Citations

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Abstract

To examine the structural parameters necessary for antiviral efficacy of certain purine nucleosides, several 9-beta-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-beta-D-ribofuranosyl-6-iodopurine with cyanide ion. Certain 2-amino- and 2-methyl-9-beta-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-beta-D-Ribofuranosylpurine-6-carboxamide (6a), the corresponding 6-thiocarboxamide (7b), and 4-amino-8-(beta-D-ribofuranosylamino)pyrimido[5,4-d]pyrimidine (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 55% survival rate on day 21 compared to a 30% survival in the controls.

In Vitro Study

Study Snapshot

9-beta-D-ribofuranosylpurine-6-carboxamides show significant in vitro antiviral activity and show 55% survival rate in mice infected with Rift Valley fever virus at 50 mg/kg/day.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis and antiviral activity of certain 9-beta-D-ribofuranosylpurine-6-carboxamides.

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References

Citations

Direct Minisci-Type C–H Amidation of Purine Bases

This study presents a metal-free, cheap, and scalable method for direct C-H amidation of purines, enabling late-stage functionalizations of biologically important molecules.

Bicyclic 6 + 6 systems: the chemistry of pyrimido[4,5-d]pyrimidines and pyrimido[5,4-d]pyrimidines

Pyrimido[4,5-d]pyrimidine and pyrimido[5,4-d]pyrimidine analogs have significant chemistry and biological significance, with applications in medical and pharmaceutical fields.

SAR studies of 9-norbornylpurines as Coxsackievirus B3 inhibitors.

The 6-chloropurine derivative is the most active compound in a series of 9-norbornylpurines as Coxsackievirus B3 inhibitors at low-micromolar concentrations.

Synthesis and in vitro evaluation of substituted pyrimido[5,4-d]pyrimidines as a novel class of anti-Mycobacterium tuberculosis agents.

Substituted pyrimido[5,4-d]pyrimidines show high antibacterial activity against Mycobacterium tuberculosis, with potential for further development as a novel class of antitubercular agents.

A Mild Approach to the Synthesis of 4-Amino-8-(arylamino)pyrimido[5,4-d]pyrimidine 3-Oxides

This study presents a mild approach for the synthesis of 4-Amino-8-(arylamino)pyrimido[5,4-d]pyrimidine 3-Oxides by reacting benzylhydroxylamine with 6-cyanopurines, leading to the Dimroth-rearranged product.