C-5’-Triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides: Synthesis and biological evaluation

Abstract

A novel series of 2’-oxa-3’-aza-4’a-carbanucleosides, featured with a triazole linker at the 5’-position, has been developed by exploiting a click chemistry reaction of 5’-azido-2’-oxa-3’-aza-4’a-carbanucleosides with substituted alkynes. Biological tests indicate an antitumor activity for the synthesized compounds: most of them inhibit cell proliferation of Vero, BS-C-1, HEp-2, MDCK, and HFF cells with a CC50 in the range of 5.0–40 μM. The synthesized compounds do not show any antiviral activity.

Keywords

• antitumor activity
• click chemistry
• 1,3-dipolar cycloaddition
• nucleic acids
• 2’-oxa-3’-aza-4’a-carbanucleoside analogs