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.

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

MACCHIA, MARCO;BERTINI, SIMONE;DI BUSSOLO, VALERIA;FOGLI, STEFANO;MINUTOLO, FILIPPO;RAPPOSELLI, SIMONA;DANESI, ROMANO
2003

Abstract

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.
Macchia, Marco; M., Antonello; Bertini, Simone; DI BUSSOLO, Valeria; Fogli, Stefano; E., Giovannetti; Minutolo, Filippo; Rapposelli, Simona; Danesi, Romano
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/187565
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