Synthesis of 7-trifluoromethyl-7-deazapurine ribonucleoside analogs and their monophosphate prodrugs

Abstract

Novel 7-trifluoromethyl-7-deazapurine ribonucleoside analogs (13a-c) and their Protides (15a-c) were successfully synthesized from ribolactol or 1-α-bromo-ribose derivatives using Silyl-Hilbert-Johnson or nucleobase-anion substitution reactions followed by key aromatic trifluoromethyl substitution. Newly prepared compounds were evaluated against a panel of RNA viruses, including HCV, Ebola or Zika viruses.

Keywords:

• 7-trifluoromethyl-7-deazapurine ribonucleoside
• protides
• Silyl-Hilbert-Johnson
• RNA viruses

Additional information

Funding

This work was supported in part by NIH Grant 5P30-AI-50409 (CFAR), BB 21 Plus and the Dong-A University research fund (Korea).