Conformationally restrained ceramide analogues: Effects of lipophilic modifications on the antiproliferative activity

Marco Macchia, Michela Antonello, Simone Bertini, Valeria Di Bussolo, Stefano Fogli, Elisa Giovannetti, Filippo Minutolo, Simona Rapposelli, Romano Danesi

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2 Citations (Scopus)


Conformationally restrained analogues of ceramide containing thiouracil or uracil moieties in their polar head, substituted with an ethyl group in their 6-positions, proved to inhibit cell proliferation and induce apoptosis. A series of new thiouracil and uracil analogues of ceramide possessing several 6-alkyl- or 6-arylalkyl-substituents, were synthesized and tested as inhibitors of cell proliferation. The lipophilic substituents introduced in the 6-position were pure alkyls (n-propyl, n-butyl, i-butyl, neo-pentyl), or aryl-alkyls (2-phenylethyl). Although a significant antiproliferative activity was maintained in most compounds synthesized, none of them showed any improvement with respect to their 6-ethyl-substituted counterparts.

Original languageEnglish
Pages (from-to)85-89
Number of pages5
Issue number1
Publication statusPublished - 1 Jan 2003


  • Apoptosis
  • Ceramide analogues
  • Lipophilicity
  • Thiouracil
  • Uracil

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