Synthesis and Biological Evaluation of Some 1,2-Disubstituted Benzimidazole Derivatives as New Potential Anticancer Agents

YURTTAŞ L., DEMİRAYAK Ş., AKALIN ÇİFTÇİ G., Yildirim S. U., KAPLANCIKLI Z. A.

ARCHIV DER PHARMAZIE, vol.346, no.5, pp.403-414, 2013 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 346 Issue: 5
  • Publication Date: 2013
  • Doi Number: 10.1002/ardp.201200452
  • Journal Name: ARCHIV DER PHARMAZIE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.403-414
  • Keywords: Anticancer activity, Benzimidazole, BrdU, Flow cytometric analysis, Thioamide, ANTIPROLIFERATIVE ACTIVITY, ANTITUMOR-ACTIVITY, CELLS, APOPTOSIS, GROWTH, ASSAY
  • Anadolu University Affiliated: Yes

Abstract

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 WillgerodtKindler reaction to give 2-[(morpholine-4-yl)thioxomethyl]benzimidazole. Then, the obtained compound was reacted with appropriate -bromoacetophenone derivatives in the presence of potassium carbonate to give the final products. Structure elucidation of the final compounds was achieved by FT-IR, 1H 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.