Discovery and structure-activity relationships of (2-(arylthio)benzylideneamino)guanidines as a novel series of potent apoptosis inducers

Bioorg Med Chem. 2009 Apr 1;17(7):2852-8. doi: 10.1016/j.bmc.2009.02.029. Epub 2009 Feb 21.

Abstract

1-(2-(2,5-Dimethoxyphenylthio)benzylidene)semicarbazide (2a) was discovered as a potent apoptosis inducer through our cell based HTS assay. SAR study led to the discovery of a more aqueous soluble analog (2-(2,5-dimethoxyphenylthio)-6-methoxybenzylideneamino)guanidine (5e) with EC(50) value of 60 nM in the caspase activation assay and GI(50) value of 62 nM in the growth inhibition assay in T47D cells. Compound 5e was found to be an inhibitor of tubulin polymerization and efficacious in a MX-1 breast tumor model.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Apoptosis*
  • Benzylidene Compounds / chemical synthesis
  • Benzylidene Compounds / chemistry*
  • Benzylidene Compounds / pharmacology
  • Cell Line, Tumor
  • Drug Discovery
  • Drug Screening Assays, Antitumor
  • Guanidines / chemical synthesis
  • Guanidines / chemistry*
  • Guanidines / pharmacology
  • Humans
  • Semicarbazides / chemistry*
  • Semicarbazides / pharmacology
  • Structure-Activity Relationship
  • Tubulin Modulators / chemical synthesis
  • Tubulin Modulators / chemistry*
  • Tubulin Modulators / pharmacology

Substances

  • (2-(2,5-dimethoxyphenylthio)-6-methoxybenzylideneamino)guanidine
  • 1-(2-(2,5-dimethoxyphenylthio)benzylidene)semicarbazide
  • Antineoplastic Agents
  • Benzylidene Compounds
  • Guanidines
  • Semicarbazides
  • Tubulin Modulators