Synthesis and cytotoxic evaluation of usnic acid benzylidene derivatives as potential anticancer agents

Nat Prod Res. 2021 Apr;35(7):1097-1106. doi: 10.1080/14786419.2019.1639176. Epub 2019 Jul 13.

Abstract

A series of usnic acid benzylidene derivatives (groups I-V) were designed, synthesized and evaluated for their anticancer activity in the search for potentially new anticancer agents. Compounds 1a, 5b, 2b, 2e and 2f exhibited the most potent cytotoxcity against K562 cell line with IC50 values of 10.0 ± 3.6, 5.6 ± 0.4, 8.8 ± 1.0, 4.5 ± 0.1 and 8.4 ± 0.4 μM, respectively. It is noteworthy that compound 2e displayed potent cytotoxicity against K562 cells without any cytotoxic effect on HEK293 normal cell line.

Keywords: Usnic acid; aldol condensation; benzylidene derivative; cytotoxicity.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry
  • Benzofurans / pharmacology*
  • Benzylidene Compounds / chemical synthesis*
  • Benzylidene Compounds / chemistry
  • Benzylidene Compounds / pharmacology*
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Cell Death / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • HEK293 Cells
  • Humans
  • K562 Cells
  • Proton Magnetic Resonance Spectroscopy
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Benzofurans
  • Benzylidene Compounds
  • usnic acid