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4 results on '"Stewart, W"'

1. 5′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral Study

Author

Qi Chen, Stewart W. Schneller, Chong Liu, Kathryn L. Jones, and Tyler Singer

Subjects
antivirals, carbocyclic nucleosides, neplanocin, Ullmann reaction, Organic chemistry, QD241-441
Abstract

The arbocyclic nucleosides aristeromycin and neplanocin have been studied as a source for new antiviral agents. A convenient synthesis of C-5′-truncated 3-deaza-1′,6′-isoneplanocin, which combines the features of antiviral candidates 5′-noraristeromycin and 3-deaza-1′,6′-isoneplanocin is reported from (−)-cyclopentenone to give the two C-4′ epimers of 5′-nor-3-deaza isoneplanocin. Antiviral assays showed activity against the JC virus (EC50 = 1.12 µM for (4′R)-8; EC50 = 59.14 µM for (4′S)-7) and inactivity of both compounds against several DNA and RNA viruses. Both compounds lacked cytotoxicity.

Published
2020
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2. 3,7-Dideazaneplanocin: Synthesis and antiviral analysis

Author

Xue-qiang Yin and Stewart W. Schneller

Subjects
0301 basic medicine, Hydrolases, Pyridones, Carbocyclic nucleosides, Molecular Conformation, Microbial Sensitivity Tests, 010402 general chemistry, Antiviral Agents, 01 natural sciences, Molecular conformation, 03 medical and health sciences, chemistry.chemical_compound, neplanocin, Hydrolase, RNA Viruses, Enzyme Inhibitors, DNA Viruses, RNA, Original Articles, General Medicine, In vitro, 0104 chemical sciences, 3. Good health, 030104 developmental biology, chemistry, Biochemistry, antiviral activity, Phosphorylation, 3,7-dideazaadenine nucleosides, DNA
Abstract

Objective To synthesize 3,7-dideazaneplanocin and evaluate its antiviral potential. Methods The target 3,7-dideazaneplanocin has been prepared in five steps from a readily available cyclopentenol. A thorough in vitro antiviral analysis was conducted versus both DNA and RNA viruses. Results A rational synthesis of 3,7-dideazaneplanocin was conceived and successfully pursued in such a way that it can be adapted to various analogs of 3,7-dideazaneplanocin. Using standard antiviral assays, no activity for 3,7-dideazaneplanocn was found. Conclusion Two structural features are necessary for adenine-based carbocyclic nucleosides (like neplanocin) for potential antiviral properties: (i) inhibition of S-adenosylhomocysteine hydrolase and/or (ii) C-5′ activation via the mono-nucleotide. These two requisite adenine structural features to fit these criteria are not present in in the target 3,7-dideazaneplanocin: (i) an N-7 is necessary for inhibition of the hydrolase and the N-3 is claimed to be essential for phosphorylation at C-5′. Thus, it is not surprising that 3,7-dideazaneplaoncin lacked antiviral properties.

Published
2017

3. 5′-Hydroxy-5′-homoaristeromycin: Synthesis and antiviral properties

Author

Chong Liu, Qi Chen, Terry L. Bowlin, and Stewart W. Schneller

Subjects
Hepatitis B virus, Adenosine, Stereochemistry, C-4′ aristeromycin derivatives, Clinical Biochemistry, Congenital cytomegalovirus infection, Carbocyclic nucleosides, Molecular Conformation, Pharmaceutical Science, Cytomegalovirus, Microbial Sensitivity Tests, 010402 general chemistry, 01 natural sciences, Biochemistry, Antiviral Agents, Article, Structure-Activity Relationship, Drug Discovery, medicine, Cytotoxic T cell, Humans, Molecular Biology, ComputingMethodologies_COMPUTERGRAPHICS, Dose-Response Relationship, Drug, 010405 organic chemistry, Chemistry, Organic Chemistry, Diastereomer, Hepatitis B, medicine.disease, 5'-homoaristeromycin, 0104 chemical sciences, Molecular Medicine
Abstract

Graphical abstract, Synthetically combining the C-4′ side-chain structural features of the antiviral candidates 5′-methylaristeromycin and 5′-homoaristeromycin into a diastereomeric pair of C-4′ side-chain dihydroxylated aristeromycins (6 and 7) is reported. Broad antiviral analyses of the both targets found promising effects towards HBV (6, 6.7 μM and 7, 7.74 μM) and HCMV (only 7, 0.72 μM). No other activity was found. Neither of the diastereomers was cytotoxic in the assays performed.

Published
2018

4. 5′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral Study.

Author

Chen, Qi, Schneller, Stewart W., Liu, Chong, Jones, Kathryn L., Singer, Tyler, and Seley-Radtke, Katherine

Subjects
*ANTIVIRAL agents, *JOHN Cunningham virus, *DNA viruses, *RNA viruses, *NUCLEOSIDES
Abstract

The arbocyclic nucleosides aristeromycin and neplanocin have been studied as a source for new antiviral agents. A convenient synthesis of C-5′-truncated 3-deaza-1′,6′-isoneplanocin, which combines the features of antiviral candidates 5′-noraristeromycin and 3-deaza-1′,6′-isoneplanocin is reported from (−)-cyclopentenone to give the two C-4′ epimers of 5′-nor-3-deaza isoneplanocin. Antiviral assays showed activity against the JC virus (EC50 = 1.12 µM for (4′R)-8; EC50 = 59.14 µM for (4′S)-7) and inactivity of both compounds against several DNA and RNA viruses. Both compounds lacked cytotoxicity. [ABSTRACT FROM AUTHOR]

Published
2020
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