Related Experiment Video
Updated: Aug 4, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
Synthesis and biological activities of 4-O-(difluoromethyl)-5-substituted-uracil nucleoside analogues
J Reefschläger1, C D Pein, D Cech
1Medical Department (Charité), Humboldt University of Berlin, GDR.
Abstract:
Various 4-O-difluoromethyl analogues of 5-substituted uridine (Urd), 2'-deoxyuridine (dUrd), and arabinofuranosyluracil (araU) nucleosides were prepared via a CF2-insertion reaction into 4-O-silylated nucleosides and evaluated for activity against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) and cytotoxicity in human embryonic lung fibroblast (HELF) cell cultures. The introduction of the 4-substituent led to a strong reduction of antiviral activity for dUrd but not for araU analogues. Three of the 4,5-disubstituted uracil nucleoside derivatives, 4-O-(difluoromethyl)-5-bromo-araU (5c),-5-methyl-araU (5e), and -(E)-5-(2-bromovinyl)-araU (5g), displayed a high and selective inhibitory effect against HSV-1, but only 5e was effective against both HSV-1 and HSV-2 comparably with the antiherpes potential of the reference compounds 9-[(2-hydroxyethoxy)methyl]guanine (acyclovir) and 1-beta-D-arabino-furanosylthymine (araT).
More Related Videos
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
10:24NMR-Based Activity Assays for Determining Compound Inhibition, IC50 Values, Artifactual Activity, and Whole-Cell Activity of Nucleoside Ribohydrolases
Published on: June 30, 2019
Related Concept Videos
DNA Base Pairing
Pharmacogenetics of Drug Targets: β₂-Adrenergic Receptors, Apo E, Thymidylate Synthase
Biosynthesis of Polysaccharides
Biosynthesis of Nucleic Acids
Inhibitors of Bacterial DNA Synthesis
Antiviral Nucleoside Inhibitors