102302-66-9Relevant academic research and scientific papers
ZUR SYNTHESE VON DIFLUOROMETHYLETHERN VERSHIEDEN SUBSTITUIERTER PYRIMIDINNUCLEOSIDE DURCH REAKTION MIT DIFLUORCARBEN
Pein, C.-D.,Cech, D.
, p. 4915 - 4918 (1985)
The reaction of CF2 with different substituted persilylated pyrimidine nucleosides either in the ribo-, 2'-deoxyribo- or in the arabino-series gave the corresponding 4-O-difluoromethylethers.Optimum yields were obtained using Hg(CF3)2 as source of CF2.
Synthesis and biological activities of 4-O-(difluoromethyl)-5-substituted-uracil nucleoside analogues
Reefschlager,Pein,Cech
, p. 393 - 397 (1988)
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-β-D-arabinofuranosylthymine (araT).
