Microwave-Assisted Three-Component Synthesis of Novel N-Arylated-Dihydrobenzo[g]quinoline-5,10-Diones and Their Potential Cytotoxic Activity

Chem Biodivers. 2022 Aug;19(8):e202200359. doi: 10.1002/cbdv.202200359. Epub 2022 Aug 3.

Abstract

A convenient three-component synthetic approach was developed en route to new and significative N-arylated-dihydrobenzo[g]quinoline-5,10-diones using 2-hydroxy-1,4-naphthoquinone, a variety of aromatic aldehydes, and 4-(arylamino)furan-2(5H)-ones. A sequence of steps including Knoevenagel condensation, Michael addition, [1,3]-hydrogen shift, intramolecular cyclization and dehydration led to the formation of products. All the products were structurally characterized by spectroscopic techniques and assessed in terms of their cytotoxicity profile against four cancer cell lines (KB, HepG2, A549, and MCF7), and human embryonic kidney (Hek-293) cell lines.

Keywords: N-arylated-dihydrobenzo[g]quinoline-5,10-diones; aza-anthraquinone; cytotoxicity profile; microwave-assisted three-component reaction; γ-butyrolactone.

MeSH terms

  • Antineoplastic Agents* / pharmacology
  • Cyclization
  • HEK293 Cells
  • Humans
  • Microwaves
  • Quinolines* / chemistry

Substances

  • Antineoplastic Agents
  • Quinolines