Green Synthesis and Electrochemical Properties of Mono- and Dimers Derived from Phenylaminoisoquinolinequinones

Molecules. 2019 Nov 30;24(23):4378. doi: 10.3390/molecules24234378.

Abstract

In the search for new quinoid compounds endowed with potential anticancer activity, the synthesis of novel heterodimers containing the cytotoxic 7-phenylaminoisoquinolinequinone and 2-phenylaminonaphthoquinone pharmacophores, connected through methylene and ethylene spacers, is reported. The heterodimers were prepared from their respective isoquinoline and naphthoquinones and 4,4'-diaminodiphenyl alkenes. The access to the target heterodimers and their corresponding monomers was performed both through oxidative amination reactions assisted by ultrasound and CeCl3·7H2O catalysis "in water". This eco-friendly procedure was successfully extended to the one-pot synthesis of homodimers derived from the 7-phenylaminoisoquinolinequinone pharmacophore. The electrochemical properties of the monomers and dimers were determined by cyclic and square wave voltammetry. The number of electrons transferred during the oxidation process, associated to the redox potential EI1/2, was determined by controlled potential coulometry.

Keywords: amination reaction; cyclic voltammetry; green synthesis; half-wave potential; heterodimers; twin drugs.

MeSH terms

  • Aniline Compounds / chemistry*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Chemical Phenomena*
  • Chemistry Techniques, Synthetic*
  • Electrochemistry / methods
  • Green Chemistry Technology*
  • Humans
  • Isoquinolines / chemical synthesis
  • Isoquinolines / chemistry*
  • Molecular Structure
  • Polymers

Substances

  • Aniline Compounds
  • Antineoplastic Agents
  • Isoquinolines
  • Polymers