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, cilt.346, sa.5, ss.403-414, 2013 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 346 Sayı: 5
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1002/ardp.201200452
  • Dergi Adı: ARCHIV DER PHARMAZIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Sayfa Sayıları: ss.403-414
  • Anahtar Kelimeler: Anticancer activity, Benzimidazole, BrdU, Flow cytometric analysis, Thioamide, ANTIPROLIFERATIVE ACTIVITY, ANTITUMOR-ACTIVITY, CELLS, APOPTOSIS, GROWTH, ASSAY
  • Anadolu Üniversitesi Adresli: Evet

Özet

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.