254878-63-2Relevant academic research and scientific papers
Synthesis of fluorinated sphinganine and dihydroceramide analogues
De Jonghe, Steven,Van Overmeire, Ilse,Van Calenbergh, Serge,Hendrix, Chris,Busson, Roger,De Keukeleire, Denis,Herdewijn, Piet
, p. 3177 - 3183 (2007/10/03)
With the aim of uncovering inhibitors of dihydroceramide desaturase and ceramide synthase and studying their substrate specificity, the synthesis of short-chain 3-fluorosphinganine and 3-fluorodihydroceramide analogues was effected. The synthesis starts from the known alkynols 1 and 10, respectively, and from the Garner aldehyde 15. The key step is the introduction of a fluorine atom using diethylaminosulfur trifluoride, which proceeds efficiently for erythro-alcohols 2 and 16, but gives rise to cyclization reactions for threo compounds 11 and 17.
Synthesis and apoptogenic activity of fluorinated ceramide and dihydroceramide analogues
De Jonghe, Steven,Van Overmeire, Ilse,Gunst, Johan,De Bruyn, Andre,Hendrix, Chris,Van Calenbergh, Serge,Busson, Roger,De Keukeleire, Denis,Philippe, Jan,Herdewijn, Piet
, p. 3159 - 3164 (2007/10/03)
Short-chain 3-fluoro-(dihydro)ceramide analogues are synthesized from L-serine using diethylaminosulfur trifluoride (DAST) as fluorinating agent. The apoptogenic activity of these compounds was measured in three different cell lines and compared with their hydroxylated counterparts.
