Synthesis and anticancer activity of some 1,2,3-trisubstituted pyrazinobenzimidazole derivatives.
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, (1)H-NMR, (13)C-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.
Department of Pharmaceutical Chemistry, Medipol University , İstanbul , Turkey and.
Şeref
Ş
Demirayak
Leyla
L
Yurttaş
D000098:Acetophenones / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D001596:Benzylamines / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D002945:Cisplatin / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D006801:Humans; D008558:Melphalan / Q000494:pharmacology; D015394:Molecular Structure; D011188:Potassium / Q000737:chemistry; D011719:Pyrazines / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000098:Acetophenones; D000970:Antineoplastic Agents; D001562:Benzimidazoles; D001596:Benzylamines; D002254:Carbonates; D011719:Pyrazines; C037593:potassium carbonate; D002945:Cisplatin; D008558:Melphalan; D011188:Potassium
1,2-disubstituted benzimidazole; anticancer activity; pyrazino[1,2-a]benzimidazole; α,β-unsaturated carbonyl