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.
Zhang
Hongwang
H
The University of Georgia College of Pharmacy, Athens, GA 30602, USA.
Schinazi
Raymond F
RF
Chu
Chung K
CK
D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015497:HIV-1 / Q000187:drug effects* / Q000302:isolation & purification; D006801:Humans; D015394:Molecular Structure
D019380:Anti-HIV Agents; C031300:neplanocin F; D000241:Adenosine