Design, synthesis, and biological evaluation of combretabenzodiazepines: a novel class of anti-tubulin agents

J Med Chem. 2015 Feb 12;58(3):1345-57. doi: 10.1021/jm5016389. Epub 2015 Jan 27.

Abstract

In the present manuscript, starting from the 1,4-benzodiazepin-2-one nucleus, a privileged structure in medicinal chemistry, we have synthesized a novel class of cis-locked combretastatins named combreatabenzodiazepines. They show similar cytotoxic and antitubulin activity compared to combretastatin A-4 in neuroblastoma cells, showing a better pharmacokinetic profile. This class of compounds has therefore the potential for further development as antitubulin agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Benzodiazepinones / chemical synthesis
  • Benzodiazepinones / chemistry
  • Benzodiazepinones / pharmacology*
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Drug Screening Assays, Antitumor
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Structure-Activity Relationship
  • Tubulin / metabolism*
  • Tubulin Modulators / chemical synthesis*
  • Tubulin Modulators / chemistry
  • Tubulin Modulators / pharmacology*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Benzodiazepinones
  • Tubulin
  • Tubulin Modulators