Synthesis of neplanocin F analogues as potential antiviral agents

• Published in: Bioorganic & medicinal chemistry Vol. 14; no. 24; pp. 8314 - 8322
• Main Authors: Zhang, Hongwang, Schinazi, Raymond F., Chu, Chung K.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 15.12.2006; Elsevier Science
• Subjects: Adenosine - analogs & derivatives; Adenosine - chemical synthesis; Adenosine - chemistry; Adenosine - pharmacology; Anti-HIV Agents - chemical synthesis; Anti-HIV Agents - chemistry; Anti-HIV Agents - pharmacology; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antiviral agents; Biological and medical sciences; HIV-1 - drug effects; HIV-1 - isolation & purification; Human immunodeficiency virus; Humans; Medical sciences; Molecular Structure; Pharmacology. Drug treatments; Adenine derivatives; Human; Purine derivatives; HIV-1 virus; Retroviridae; Cytotoxicity; Carbanucleoside; Lentivirus; In vitro; Biological activity; Virus; Antiviral; Nucleoside; Human immunodeficiency virus; Chemical synthesis; Lymphocyte
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2006.09.007

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.