Synthesis, spectroscopic characterization and antiproliferative evaluation in vitro of novel Schiff bases related to benzimidazoles

Eur J Med Chem. 2011 Jun;46(6):2274-9. doi: 10.1016/j.ejmech.2011.03.008. Epub 2011 Mar 10.

Abstract

A series of novel benzimidazole substituted Schiff bases were synthesized by reaction of aromatic aldehydes with corresponding 2-aminobenzimidazoles. Their structure has been studied by 1H and 13C NMR, IR and UV/Vis spectroscopy. Majority of prepared Schiff bases were tested on their antiproliferative activity in vitro and exerted non-specific antiproliferative activity on the tested cell lines at the highest tested concentration. Compounds 18 and 19 exerted the strongest non-specific antiproliferative effect on all cell lines and a concentration-dependent effect on HeLa and MCF-7 cell lines at micromolar concentrations but simultaneously being highly cytotoxic on human fibroblasts as well.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology*
  • Cell Cycle / drug effects
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Fibroblasts / drug effects
  • HeLa Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Schiff Bases / chemical synthesis
  • Schiff Bases / chemistry
  • Schiff Bases / pharmacology*
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Benzimidazoles
  • Schiff Bases