1. 5′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral Study
- Author
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Qi Chen, Kathryn L. Jones, Stewart W. Schneller, Chong Liu, and Tyler Singer
- Subjects
2019-20 coronavirus outbreak ,Adenosine ,Coronavirus disease 2019 (COVID-19) ,JC virus ,Pharmaceutical Science ,010402 general chemistry ,medicine.disease_cause ,Antiviral Agents ,01 natural sciences ,Analytical Chemistry ,Ullmann reaction ,lcsh:QD241-441 ,chemistry.chemical_compound ,antivirals ,lcsh:Organic chemistry ,neplanocin ,Drug Discovery ,medicine ,Humans ,RNA Viruses ,Physical and Theoretical Chemistry ,Cytotoxicity ,010405 organic chemistry ,Chemistry ,Communication ,Organic Chemistry ,RNA ,JC Virus ,Virology ,0104 chemical sciences ,Chemistry (miscellaneous) ,carbocyclic nucleosides ,Molecular Medicine ,Epimer ,DNA - 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