Triggering the directional selectivity of a ring-closure reaction leads to pyridoazacarbazoles with anticancer properties

Chemistry. 2015 Apr 27;21(18):6668-72. doi: 10.1002/chem.201500156. Epub 2015 Mar 30.

Abstract

We herein describe a facile and versatile synthetic route to the tetracyclic system of 6-substituted 5,6-dihydro-11H-pyrido[3,2-i]-1-azacarbazoles with promising anticancer properties. These derivatives are built up by an elegant one-step base-catalyzed synthetic procedure from commercially available building blocks. One additional step provides the corresponding skeleton hitherto unknown in the literature. The possibility to synthesize a large library of compounds with various substitution patterns utilizing this method underlines the importance of this synthetic procedure.

Keywords: antitumor agents; heterocycles; one-step synthesis; pyridoazacarbazoles; synthetic methods.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Carbazoles / chemical synthesis*
  • Carbazoles / chemistry
  • Carbazoles / pharmacology
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Cyclization
  • Humans
  • Molecular Structure
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / pharmacology

Substances

  • Antineoplastic Agents
  • Carbazoles
  • Pyridines