Grindstone Chemistry: Design, One-Pot Synthesis, and Promising Anticancer Activity of Spiro[acridine-9,2'-indoline]-1,3,8-trione Derivatives against the MCF-7 Cancer Cell Line

Molecules. 2020 Dec 11;25(24):5862. doi: 10.3390/molecules25245862.

Abstract

In this study, the synthesis of one-pot 10-phenyl-3,4,6,7-tetrahydro-1H-spiro [acridine-9,2'-indoline]-1,3,8-trione derivatives was achieved via a four-component cyclocondensation reaction, which was carried out in solvent-free conditions, and using p-toluenesulfonic acid (p-TSA) as a catalyst. The product was confirmed by FT-IR, 1H-NMR, 13C-NMR, mass spectra, and elemental analysis. Furthermore, the anticancer activity was screened for all compounds. Among these compounds, compound 1c was more effective (GI50 0.01 µm) against MCF-7 cancer cell lines than standard and other compounds. Therefore, the objective of this study was achieved with a few promising molecules having been demonstrated to be potential anticancer agents.

Keywords: anticancer activity; cyclocondensation; grinding; indole; isatin; p-TSA catalyst; solvent-free conditions.

MeSH terms

  • Antineoplastic Agents / pharmacology*
  • Benzenesulfonates / chemistry
  • Catalysis
  • Chemistry Techniques, Synthetic*
  • Combinatorial Chemistry Techniques
  • Drug Design
  • Drug Screening Assays, Antitumor*
  • Humans
  • MCF-7 Cells
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Solvents
  • Spectroscopy, Fourier Transform Infrared
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology*

Substances

  • Antineoplastic Agents
  • Benzenesulfonates
  • Solvents
  • Spiro Compounds
  • 4-toluenesulfonic acid