Stereoselective ring contraction of 2,5-diketopiperazines : An innovative approach to the synthesis of promising bioactive 5-membered scaffolds

Thilbault Coursindel (1) , Audrey Restouin (2) , Georges Dewynter (1) , Jean Martinez (1) , Yves Collette (2) , Isabelle Parrot (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
2 CRCM / U891 Inserm - Centre de Recherche en Cancérologie de Marseille

Ring contraction of 2,5-diketopiperazines by TRAL-alkylation led us to the stereoselective synthesis of original pyrrolidine-2,4-diones, a novel series of promising molecules with moderate antiproliferative activity on breast cancer cells.

Mots clés: Ring contraction; Diketopiperazines; Stereoselective rearrangement; Spiroheterocycle; Anti-proliferative activity

Domaines: Chimie organique

Thilbault Coursindel, Audrey Restouin, Georges Dewynter, Jean Martinez, Yves Collette, et al.. Stereoselective ring contraction of 2,5-diketopiperazines : An innovative approach to the synthesis of promising bioactive 5-membered scaffolds. Bioorganic Chemistry, 2010, 38, pp.210-217. ⟨10.1016/j.bioorg.2010.05.002⟩. ⟨hal-00599350⟩