Synthesis and biological evaluation of 3-(4-substituted-phenyl)-N-hydroxy-2-propenamides, a new class of histone deacetylase inhibitors

J Med Chem. 2003 Dec 18;46(26):5745-51. doi: 10.1021/jm030377q.

Abstract

Inhibitors of histone deacetylases (HDACs) have been shown to induce differentiation and/or apoptosis of human tumor cells. Novel 3-(4-substituted-phenyl)-N-hydroxy-2-propenamides have been prepared as a new class of HDAC inhibitors and evaluated for their antiproliferative activity and HDAC inhibitory activity. Incorporation of a 1,4-phenylene carboxamide linker, shown by 5, and a 4-(dimethylamino)phenyl or 4-(pyrrolidin-1-yl)phenyl group as a cap substructure generated highly potent hydroxamic acid-based HDAC inhibitors 5a and 5b.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Benzamides / chemical synthesis*
  • Benzamides / chemistry
  • Benzamides / pharmacology
  • Binding Sites
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Histone Deacetylase Inhibitors*
  • Humans
  • Hydroxamic Acids / chemical synthesis*
  • Hydroxamic Acids / chemistry
  • Hydroxamic Acids / pharmacology
  • Models, Molecular
  • Protein Binding
  • Structure-Activity Relationship

Substances

  • 4-dimethylamino-N-(4-(2-hydroxycarbamoylvinyl)benzyl)benzamide
  • Antineoplastic Agents
  • Benzamides
  • Histone Deacetylase Inhibitors
  • Hydroxamic Acids
  • N-(4-(2-hydroxycarbamoylvinyl)benzyl)-4-pyrrolidin-1-ylbenzamide