New palbociclib analogues modified at the terminal piperazine ring and their anticancer activities

Eur J Med Chem. 2016 Oct 21:122:546-556. doi: 10.1016/j.ejmech.2016.07.020. Epub 2016 Jul 12.

Abstract

A series of new palbociclib analogs by extensive functionalization of the tail piperazine ring with various carbamates and amides have been synthesized. All the palbociclib derivatives were evaluated for their cytotoxic activities against MCF-7 cell line. From the anti-proliferation activity results, two of the tested compounds (compounds 4d and 4e) showed significant cytotoxic effects. And compounds 4d and 4e exhibited potent anticancer activities in MDA-MB-453 and MDA-MB-231 cells. Among these derivatives compound 4e was found to possess cytotoxicity that is better than standard drug palbociclib. Moreover, compound 4e demonstrated robust tumor growth inhibition in vivo model.

Keywords: Anticancer; CDKs; Palbociclib; Synthesis.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cyclin-Dependent Kinase 6 / chemistry
  • Cyclin-Dependent Kinase 6 / metabolism
  • Humans
  • Molecular Docking Simulation
  • Piperazines / chemical synthesis
  • Piperazines / chemistry*
  • Piperazines / metabolism
  • Piperazines / pharmacology
  • Protein Conformation
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*
  • Pyridines / metabolism
  • Pyridines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Piperazines
  • Pyridines
  • Cyclin-Dependent Kinase 6
  • palbociclib