Synthesis and biological assessment of indole derivatives containing penta-heterocycles scaffold as novel anticancer agents towards A549 and K562 cells

J Enzyme Inhib Med Chem. 2023 Dec;38(1):2163393. doi: 10.1080/14756366.2022.2163393.

Abstract

Herein, a new series of 2-chloro-N-(5-(2-oxoindolin-3-yl)-4H-pyrazol-3-yl) acetamide derivatives containing 1,3,4-thiadiazole (10a-i) and 4H-1,2,4-triazol-4-amine (11a-r) moiety was designed, synthesised as novel anticancer agents. The antiproliferative activity values indicated that compound 10 b stood as the most potent derivative with IC50 values of 12.0 nM and 10 nM against A549 and K562 cells, respectively. Mechanism investigation and docking studies of 10 b indicated that it possessed good apoptosis characteristic and dose-dependent growth arrest of A549 and K562 cells, blocked cell cycle into G2/M phase. Interestingly, 10 b suppressed the growth of A549 and K562 cells via modulation of EGFR and p53-MDM2 mediated pathway.

Keywords: Indole derivatives; anticancer; molecular docking; penta-heterocycle.

MeSH terms

  • Antineoplastic Agents*
  • Apoptosis
  • Cell Line, Tumor
  • Cell Proliferation
  • Drug Screening Assays, Antitumor
  • Humans
  • Indoles / pharmacology
  • K562 Cells
  • Molecular Docking Simulation
  • Molecular Structure
  • Rubiaceae* / metabolism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Indoles