Synthesis of neplanocin F analogues as potential antiviral agents

Neplanocin F is a natural carbocyclic nucleoside. Herein, we describe the synthesis and antiviral activity of (±)-5′-deoxy-neplanocin F analogues. The key intermediate 4, synthesized from the commercially available (±)-2-azabicyclo[2.2.1]-hept-5-en-3-one (ABH), was utilized to prepare the target nucleosides. Among the target compounds, 5′-deoxyneplanocin F adenine exhibited moderate anti-HIV activity in human lymphocytes without any marked cytotoxicity.

Neplanocin F is a natural carbocyclic nucleoside. Herein, we describe the synthesis and antiviral activity of (±)-5′-deoxy-neplanocin F analogues. The key intermediate 4, synthesized from the commercially available (±)-2-azabicyclo[2.2.1]-hept-5-en-3-one (ABH), was utilized to prepare the target nucleosides. Among the target compounds, 5′-deoxyneplanocin F adenine exhibited moderate anti-HIV activity in human lymphocytes without any marked cytotoxicity.Figure optionsDownload as PowerPoint slide