期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 9, 期 23, 页码 8163-8170出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob06195j
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资金
- Pierre Fabre group
- CERPER (Centre d'Etude et de Recherche sur la Peau et les Epitheliums de Revetement Pierre Fabre)
New phytosphingosine analogues have been conceived, synthesised and their cytotoxicity in B16 murine melanoma cells tested. These compounds embed an isomeric substitution pattern resulting from a formal permutation of the C-2 and C-4 substituents along the aliphatic skeleton of the original sphingoid base. Five different stereoisomers have been accessed through regio- and stereocontrolled opening of the oxirane of long chain epoxyamine precursors. The corresponding N-hexyl and N-octanoyl derivatives have also been prepared. In cell viability experiments all the primary amines were found to be more active than the natural phytosphingosine with IC50 in the low mu M range for the most potent compounds.
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