Synthesis and In Vitro Cytotoxicity of Novel Halogenated Dihydropyrano[3,2-b]Chromene Derivatives

Acta Chim Slov. 2022 Dec 15;69(4):920-927. doi: 10.17344/acsi.2022.7754.

Abstract

Lung and breast cancers are among the most common cancers. In the present work, initially, 6-bromo-; and 6-chloro-3-hydroxychromone compounds were prepared. In the next step, a series of 8-bromo-; and 8-chloro-dihyropyrano[3,2-b]chromene derivatives were synthesized by one-pot three component reaction of these two compounds, aromatic aldehydes, and ethyl cyanoacetate in the presence of triethylamine in EtOH at reflux conditions. The synthesized compounds were tested for their in vitro cytotoxic activity against A549 (lung cancer) and MCF-7 (breast cancer) cell lines. It was found that some compounds have high to moderate cytotoxicity, which makes them potential candidates for further studies. This study can be the basis for further studies to design and synthesis potent anticancer compounds and investigating their mechanism of action.

Keywords: 6-bromo-3-hydroxychromone; 6-chloro-3-hydroxychromone; Cancer cell line; Chromone derivatives; Cytotoxicity; Three-component reactions.

MeSH terms

  • Antineoplastic Agents*
  • Benzopyrans / pharmacology
  • Benzopyrans / therapeutic use
  • Breast Neoplasms* / drug therapy
  • Cell Line, Tumor
  • Cell Proliferation
  • Drug Screening Assays, Antitumor
  • Female
  • Humans
  • MCF-7 Cells
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Benzopyrans
  • Antineoplastic Agents