Synthesis, activity evaluation, and docking analysis of barbituric acid aryl hydrazone derivatives as RSK2 inhibitors

J Enzyme Inhib Med Chem. 2013 Aug;28(4):747-52. doi: 10.3109/14756366.2012.681651. Epub 2012 Apr 30.

Abstract

The 90 kDa ribosomal S6 kinases (RSKs), especially RSK2, have attracted attention for the development of new anticancer agents. Through structural optimization of the hit compound 1 from our previous study, a series of barbituric acid aryl hydrazone analogues were designed and synthesized as potential RSK2 inhibitors. The most potent one, compound 9, showed a higher activity against RSK2 with an IC50 value of 1.95 μM. To analyze and elucidate their structure-activity relationship, the homology model of RSK2 N-terminal kinase domain was built and molecular docking simulations were performed, which provide helpful clues to design new inhibitors with desired activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Barbiturates / chemical synthesis
  • Barbiturates / chemistry
  • Barbiturates / pharmacology*
  • Dose-Response Relationship, Drug
  • Humans
  • Hydrazones / chemical synthesis
  • Hydrazones / chemistry
  • Hydrazones / pharmacology*
  • Models, Molecular
  • Molecular Structure
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Ribosomal Protein S6 Kinases, 90-kDa / antagonists & inhibitors*
  • Ribosomal Protein S6 Kinases, 90-kDa / metabolism
  • Structure-Activity Relationship

Substances

  • Barbiturates
  • Hydrazones
  • Protein Kinase Inhibitors
  • Ribosomal Protein S6 Kinases, 90-kDa
  • barbituric acid