362607-80-5Relevant academic research and scientific papers
5-(trifluoromethyl)-β-L-2′-deoxyuridine, the L-enantiomer of trifluorothymidine: Stereospecific synthesis and antiherpetic evaluations
Salvetti, Raul,Marchand, Arnaud,Pregnolato, Massimo,Verri, Annalisa,Spadari, Silvio,Focher, Federico,Briant, Martin,Sommadossi, Jean-Pierre,Mathé, Christophe,Gosselin, Gilles
, p. 1731 - 1738 (2007/10/03)
As part of our ongoing work on β-L-nucleoside analogues as potential antiviral drugs, we have synthesized 5-(tri-fluoromethyl)-β-L-2′-deoxyuridine (L-TFT), the hitherto unknown L-enantiomer of trifluorothymidine (CF3dUrd, TFT). We have also studied the effect of L-TFT on human and herpes simplex virus (HSV) type 1 and 2 thymidine kinases, and human thymidine phosphorylase, as well as its anti-HSV-1 and anti-HSV-2 activities in cell cultures. L-TFT has been found: (i) to inhibit HSV-1 TK with activity comparable to TFT, with no effect on human TK, (ii) to be phosphorylated by the viral enzyme with similar efficiency to TFT, (iii) to be resistant, in contrast to TFT, to hydrolysis by human thymidine phosphorylase. Unfortunately, when evaluated in cell cultures, L-TFT did not show any anti-HSV-1 and anti-HSV-2 activities. Copyright
Synthesis and in vitro activity of D- and L-enantiomers of 5-(trifluoromethyl)uracil nucleoside derivatives
Salvetti,Pregnolato,Verri,Focher,Spadari,Marchand,Mathe,Gosselin
, p. 1123 - 1125 (2007/10/03)
Recently, β-L-nucleoside analogues have emerged as a new class of sugar modified nucleosides with potential antiviral and/or antitumoral activity. As a part of our ongoing research on this topic, we decided to synthesize 5-CF3-β-L-dUrd (7), the hitherto unknown L-enantiomer of Trifluridine, an antiherpetic drug approved by FDA but only used in topical applications due to concomitant cytotoxicity. 5-CF3-β-dUrd (7) as well as some other related L-nucleoside derivatives were stereospecifically prepared and tested in vitro against viral (HSV-1 and HSV-2) and human thymidine kinases (TK).
