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

DEMİRAYAK Ş., YURTTAŞ L.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, cilt.29, sa.6, ss.811-822, 2014 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 29 Sayı: 6
  • Basım Tarihi: 2014
  • Doi Numarası: 10.3109/14756366.2013.858142
  • Dergi Adı: JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.811-822
  • Anahtar Kelimeler: 1,2-disubstituted benzimidazole, alpha,beta-unsaturated carbonyl, anticancer activity, pyrazino[1,2-a]benzimidazole, EXTENDED QUINONE METHIDES, BIOREDUCTIVE ALKYLATING-AGENTS, ALPHA, INHIBITION, BENZIMIDAZOLE, LACTONES, DESIGN
  • Anadolu Üniversitesi Adresli: Evet

Özet

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 alpha-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, H-1-NMR, C-13-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.