Synthesis of D-like and L-like 5′-fluoro-5′-deoxy-1′,6′-isoneplanocins and their antiviral activity including Ebola

Abstract

In exploring the 1′,6′-isoneplanocin structural framework for antiviral compound development, both the D-like and L-like 5′-fluoro-5′-deoxy analogs have been synthesized from readily available cyclopentenyl iodides and adenine in five steps. Antiviral evaluation found D-like 5′-fluoro-5′-deoxy-1′,6′-isoneplanocin to display less broad-spectrum antiviral effects than the parent D-like including weaker activity against Ebola and norovirus. The L-like enantiomer was devoid of any activity, contrary to the parent L-like compound.