Straightforward access to enantiomerically pure 3,4-diamino-3,4-dideoxyphytosphingosines, as novel analogues of natural d-ribo-phytosphingosine was accomplished, starting from two available chirons: dimethyl l-tartrate and d-isoascorbic acid. A sequential Overman rearrangement followed by late-stage introduction of the alkyl side chain moiety via olefin cross-metathesis is the cornerstone of this approach. The preliminary evaluation study of the synthesised sphingomimetics, based on their ability to inhibit a proliferation of human cancer cells, showed promising cytotoxicity against Jurkat and HeLa cells for (2R,3R,4S)-2,3,4-triaminooctadecan-1-ol trihydrochloride.

• Klíčová slova
• Cytotoxic activity, OCM, Sequential rearrangement, Sphingoid bases, d-ribo-phytosphingosine,
• MeSH
• antitumorózní látky farmakologie   chemie   chemická syntéza   MeSH
• HeLa buňky MeSH
• Jurkat buňky MeSH
• lidé MeSH
• proliferace buněk * účinky léků   MeSH
• sfingosin * analogy a deriváty   chemie   farmakologie   chemická syntéza   MeSH
• stereoizomerie MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• antitumorózní látky MeSH
• phytosphingosine MeSH Prohlížeč
• sfingosin * MeSH