Synthesis and anticancer activity of some 1,2,3-trisubstituted pyrazinobenzimidazole derivatives

Demirayak Ş., YURTTAŞ L.

Journal of Enzyme Inhibition and Medicinal Chemistry, vol.29, no.6, pp.811-822, 2014 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 29 Issue: 6
  • Publication Date: 2014
  • Doi Number: 10.3109/14756366.2013.858142
  • Journal Name: Journal of Enzyme Inhibition and Medicinal Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.811-822
  • Keywords: 1,2-disubstituted benzimidazole, alpha,beta-unsaturated carbonyl, anticancer activity, pyrazino[1,2-a]benzimidazole
  • Istanbul Medipol University Affiliated: Yes


The synthesis of some new pyrazino[1,2-a]benzimidazole derivatives and investigation of their anticancer activities were aimed in this work. Thus, 2-acetylbenzimidazole was reacted with appropriate α-bromoacetophenones and potassium carbonate in acetone to give 2-(2-acetyl-1H-benzimidazol-1-yl)-1-phenylethanone derivatives (3a-d). These diketone compounds were reacted with varied benzylamines in acetic acid to obtain 2-benzyl-1-methylidene-3-aryl-1,2-dihydropyrazino[1,2-a]benzimidazole derivatives (4a-t). The structures of the obtained compounds were elucidated by using IR, 1H-NMR, 13C-NMR, MS spectral data and elemental analyses results. Anticancer activities of the selected compounds were investigated in National Cancer Institute, Bethesda, MD. 3c and 4n showed remarkable anticancer activity comparing with standard drugs, melphalan and cisplatin.