Synthesis and Evaluation of 2′-Deoxy-2′-Spirodiflurocyclopropyl Nucleoside Analogs

ABSTRACT

The preparation of 2′-deoxy-2′-siprodifluorocyclopropany-lnucleoside analogs has been achieved from α-d-glucose in several steps. The key step in the synthesis was the introduction of the difluorocyclopropane through a difluorocarbene type reaction at the 2′-position. Then, a series of novel 2′-deoxy-2′-spirodifluorocyclopropanyl nucleoside analogs were synthesized using the Vorbrüggen method. All the synthesized nucleosides were characterized and subsequently evaluated against hepatitis C and influenza A virus strains in vitro.

KEYWORDS:

• 2′-deoxy-2′- spirodifluorocyclopropanyl nucleosides
• hepatitis C
• influenza A

Funding

The research was supported in part by Foshan Municipal Funds for Scientific and Technological Innovation Projects (2013HK100012), Guangzhou Science and Technology Project (2014J4100222), National Natural Science Foundation of China Grant (21402205). M.H. is sponsored by CAS-TWAS President′s Fellowship for international PhD students.