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

• Published in: Molecules (Basel, Switzerland) Vol. 24; no. 23; p. 4378
• Main Authors: Ibacache, Juana Andrea, Valderrama, Jaime A, Faúndes, Judith, Danimann, Alex, Recio, Francisco J, Zúñiga, César A
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 30.11.2019; MDPI
• Subjects: Alkenes; Amination; Aniline Compounds - chemistry; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Antitumor activity; Cancer; Catalysis; Cell Line, Tumor; Chemical Phenomena; Chemistry Techniques, Synthetic; Coulometers; Coulometry; Cytotoxicity; Electrochemical analysis; Electrochemistry; Electrochemistry - methods; Green Chemistry Technology; Humans; Isoquinolines - chemical synthesis; Isoquinolines - chemistry; Molecular Structure; NMR; Nuclear magnetic resonance; Oxidation; Oxidation process; Oxidative stress; Pharmacology; Pharmacophores; Polymers; Redox potential; Square waves; Ultrasonic imaging; Voltammetry; twin drugs; cyclic voltammetry; green synthesis; heterodimers; half-wave potential; amination reaction
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules24234378

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 CeCl ·7H O 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 E , was determined by controlled potential coulometry.