Synthesis and biological evaluation of some 1,2-disubstituted benzimidazole derivatives as new potential anticancer agents

Arch Pharm (Weinheim). 2013 May;346(5):403-14. doi: 10.1002/ardp.201200452. Epub 2013 Mar 22.


The synthesis of some new 1-(2-aryl-2-oxoethyl)-2-[(morpholine-4-yl)thioxomethyl]benzimidazole derivatives and investigation of their anticancer activities were the aims of this work. 2-(Chloromethyl)benzimidazole compound was reacted with sulfur and morpholine via Willgerodt-Kindler reaction to give 2-[(morpholine-4-yl)thioxomethyl]benzimidazole. Then, the obtained compound was reacted with appropriate α-bromoacetophenone derivatives in the presence of potassium carbonate to give the final products. Structure elucidation of the final compounds was achieved by FT-IR, (1)H NMR spectroscopy and MS spectrometry. The anticancer activities of the final compounds were evaluated by MTT assay, BrdU method, and flow cytometric analysis on C6, MCF-7, and A549 tumor cells. Most of the synthesized compounds exhibited considerable selectivity against the MCF-7 and C6 cell lines.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology*
  • Breast Neoplasms / drug therapy*
  • Breast Neoplasms / pathology
  • Carcinoma, Non-Small-Cell Lung / drug therapy
  • Carcinoma, Non-Small-Cell Lung / pathology
  • Cell Line, Tumor
  • Female
  • Flow Cytometry
  • Glioma / drug therapy*
  • Glioma / pathology
  • Humans
  • Lung Neoplasms / drug therapy
  • Lung Neoplasms / pathology
  • MCF-7 Cells
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Rats
  • Spectroscopy, Fourier Transform Infrared


  • Antineoplastic Agents
  • Benzimidazoles