233253-68-4Relevant academic research and scientific papers
Asymmetric synthesis of thymine nucleoside analogues based on the isochroman core
Len, Christophe,Violeau, Bruno
, p. 4835 - 4838 (2007/10/03)
Diastereoisomeric analogues of d4T having an isochroman core as the glycone moiety have been prepared in seven steps. Starting from phthalaldehyde, two chiral centres analogous to the α/β anomers of D/L sugars were created. The first was obtained enantiom
Enantiomerical excess determination, purification and biological evaluation of (3S) and (3R) α,β-butenolide analogues of isobenzofuranone
Lipka, Emmanuelle,Vaccher, Marie-Pierre,Vaccher, Claude,Len, Christophe
, p. 501 - 504 (2007/10/03)
The asymmetric synthesis of isobenzofurane analogues, new potential antiviral agents, is reported. High performance liquid chromatography (HPLC) was the technique chosen to separate the enantiomers. We describe this chiral separation and then determine th
1,3-Dihydrobenzo[c]furan nucleoside analogues: Additional studies of the thymine derivative
Egron, David,Perigaud, Christian,Gosselin, Gilles,Aubertin, Anne-Marie,Faraj, Abdesslem,Selouane, Majid,Postel, Denis,Len, Christophe
, p. 4473 - 4475 (2007/10/03)
The detailed study of the 1,3-dihydrobenzo[c]furan derivative of thymine is reported. The lack of anti-HIV activity of this compound in cell culture experiments is shown to be related to the inability of the corresponding 5′-triphosphate derivative to int
Enantiomeric d4T analogues and their structural determination
Selouane, Abdelmajid,Vaccher, Claude,Villa, Pierre,Postel, Denis,Len, Christophe
, p. 407 - 413 (2007/10/03)
Asymmetric synthesis of d4T analogues having a benzo[c]furan moiety with two asymmetric carbon atoms was realized using Sharpless asymmetric dihydroxylation as the key step in a synthesis starting from o-phthalaldehyde. Enantiomeric purities were determin
Simple and stereoselective syntheses of nucleoside analogues with a benzo[c]furan glycone moiety
Ewing, David F.,Fahmi, NourEddine,Mackenzie, Grahame,Pranzo, Alessandra
, p. 559 - 563 (2007/10/03)
A series of d4T analogues have been synthesised in which the 2',3'- didehydro-2',3'-dideoxyribose moiety is replaced by a benzo[c]furan core. A simple strategy has been developed to access a range of compounds for biological screening. In addition, a ster
Nucleoside analogues with a novel glycone based on the benzo[c]furan core
Ewing, David F.,Fahmi, Nour-Eddine,Len, Christophe,Mackenzie, Grahame,Ronco, Gino,Villa, Pierre,Shaw, Gordon
, p. 2613 - 2630 (2007/10/03)
Routes to novel nucleoside analogues based on 1,3-dihydrobenzo[c]furan have been investigated. Thus 1-(1,3-dihydro-3-hydroxymethylbenzo[c]furan-1- yl)-thymine, an analogue of d4T, was obtained as two diastereoisomers. The cis compound (quasi β-D/α-L stereochemistry) was obtained pure but the trans compound was only 90% pure. A purine analogue with a four atom spacer group between base and glycone was also prepared. The conformation of these constrained nucleosides was studied by molecular modelling.
