Homo- and heterodimeric Smac mimetics/IAP inhibitors as in vivo-active pro-apoptotic agents. Part I: Synthesis

Leonardo Manzoni, Laura Belvisi, Aldo Bianchi, Annalisa Conti, Carmelo Drago, Marilenia De Matteo, Luca Ferrante, Eloise Mastrangelo, Paola Perego, Donatella Potenza, Carlo Scolastico, Federica Servida, Gabriele Timpano, Francesca Vasile, Vincenzo Rizzo, Pierfausto Seneci

Research output: Contribution to journalArticlepeer-review

Abstract

Novel pro-apoptotic, homo- and heterodimeric Smac mimetics/IAPs inhibitors based on the N-AVPI-like 4-substituted 1-aza-2-oxobicyclo[5.3.0]decane scaffold were prepared from monomeric structures connected through a head-head (8), tail-tail (9) or head-tail (10) linker. The selection of appropriate decorating functions for the scaffolds, and of rigid and flexible linkers connecting them, is described. The synthesis, purification and analytical characterization of each prepared dimer 8-10 is thoroughly described.

Original languageEnglish
Pages (from-to)6687-6708
Number of pages22
JournalBioorganic and Medicinal Chemistry
Volume20
Issue number22
DOIs
Publication statusPublished - Nov 15 2012

Keywords

  • Apoptosis
  • IAP inhibitors
  • Oncology
  • Peptidomimetics
  • Smac mimetics

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

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