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Both enantiomers of the isomer of neplanocin where the C-4′ hydroxymethyl has been displaced to the 6′-position (that is, 6′-isoneplanocin) have been prepared in 5 steps from known, protected iodocyclopentenones. Both products were evaluated against a number of DNA and RNA viruses and found to be inactive. This observation is suggested to be due to the displacement of the C-4′ hydroxymethyl of neplanocin (in the D-like form) away from the lysine425of S-adenosylhomocysteine hydrolase, which is important for inhibition by neplanocin and, in turn, its antiviral activity. [ABSTRACT FROM PUBLISHER]

The preparation of the C-5′ diastereomers of 5′-homoaristeromycin has been achieved in 6 steps beginning with readily available (3aR,6aR)-2,2-dimethyl-2H,3aH,4H,6aH-cyclopenta[1,3]dioxol-4-one in a Michael reaction employing chiral Evans N-acyloxazolidinones that served to direct the requisite side chain stereochemistry. The two targets were evaluated against a battery of viruses and found to possess activity only towards yellow fever. Both compounds were non-cytotoxic. [ABSTRACT FROM AUTHOR]

To extend the potential of 5′-noraristeromycin (and its enantiomer) as potential antiviral candidates, the enantiomers of the carbocyclic 5′-nor derivatives of 5′-methylthio-5′-deoxyadenosine and 5′-phenylthio-5′-deoxyadenosine have been synthesized and evaluated. None of the compounds showed meaningful antiviral activity. [ABSTRACT FROM AUTHOR]