Synthesis and Biological Evaluation of α-Tubulin-Binding Pironetin Analogues with Enhanced Lipophilicity (pages 1116–1123)
Miguel Carda, Juan Murga, Santiago Díaz-Oltra, Jorge García-Pla, Julián Paños, Eva Falomir, Chiara Trigili, J. Fernando Díaz, Isabel Barasoain and J. Alberto Marco
Article first published online: 7 JAN 2013 | DOI: 10.1002/ejoc.201201283
The preparation of four new analogues of the natural pyrone pironetin, known to bind to α-tubulin, is described. The C9 side-chain of pironetin has been replaced in one analogue by a 4-phenylbutyl chain and in the other three analogues by C13 or C16 aliphatic chains, all of them bearing two stereogenic centres. Their cytotoxic activities and interactions with tubulin have been investigated.