Synthesis of cytotoxic aza analogues of jaspine B.
A straightforward access to pyrrolidine-based analogues of jaspine B was developed. Five stereoisomers were prepared including the all-cis derivatives presenting the configuration of the natural anhydrophytosphingosine. The synthesis of the latter relied on an original Staudinger-type cyclization process. The compounds were evaluated regarding their ability to alter tumor cells' viability and to interfere with the metabolism of sphingolipids.
Rives
Arnaud
A
LSPCMIB, UMR 5068, CNRS-Université Paul Sabatier, Toulouse, France.
Ladeira
Sonia
S
Levade
Thierry
T
Andrieu-Abadie
Nathalie
N
Génisson
Yves
Y
D000818:Animals; D045744:Cell Line, Tumor; D006801:Humans; D008546:Melanoma, Experimental / Q000737:chemistry* / Q000378:metabolism; D051379:Mice; D011759:Pyrrolidines / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D013237:Stereoisomerism
D011759:Pyrrolidines; C468594:pachastrissamine; C012491:phytosphingosine; D013110:Sphingosine