Enantiomeric 3-deaza-1′,6′-isoneplanocin and its 3-bromo analogue: Synthesis by the Ullmann reaction and their antiviral properties.

The 1′,6′-isomer of neplanocin A possesses biological properties that have not been optimised through rationally conceived analogues. In that direction, this Letter reports the use of the Ullmann reaction to achieve enantiomeric 3-deaza-1′,6′-isoneplanocin and 3-bromo-3-deaza-1′,6′-isoneplanocin. These four compounds showed significant Ebola activity that is not specifically due to their inhibition of S -adenonosylhomocysteine hydrolase, as might have been expected for 3-deazaadenine carbocyclic nucleosides. For some members of this group, antiviral activity was also found against human cytomegalovirus, hepatitis B, norovirus, and measles. [ABSTRACT FROM AUTHOR]