Synthesis and antiproliferative activity in vitro of 2-aminobenzimidazole derivatives

• Published in: Farmaco (Società chimica italiana : 1989) Vol. 59; no. 2; pp. 83 - 91
• Main Authors: Nawrocka, Wanda, Sztuba, Barbara, Kowalska, Maria W, Liszkiewicz, Hanna, Wietrzyk, Joanna, Nasulewicz, Anna, Pełczyńska, Marzena, Opolski, Adam
• Format: Journal Article
• Language: English
• Published: France Elsevier SAS 01.02.2004
• Subjects: 2-Aminobenzimidazole derivatives; 2-Benzylamino-1-cinnamoylbenzimidazole; 2-Benzylaminobenzimidazoles; 2-Benzylidene; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - pharmacology; Antiproliferative activity in vitro; Benzimidazoles - chemical synthesis; Benzimidazoles - pharmacology; Cell Division - drug effects; Cell Line, Tumor; Drug Screening Assays, Antitumor; Humans; Indicators and Reagents; Magnetic Resonance Spectroscopy; Mass Spectrometry; Oxidation-Reduction; Pyrimido[1,2-a]benzimidazol-4-ones; Rhodamines; Schiff bases; Schiff Bases - chemistry; Schiff Bases - pharmacology; Spectrophotometry, Infrared; Schiff bases; 2-Benzylidene; 2-Benzylaminobenzimidazoles; 2-Aminobenzimidazole derivatives; Pyrimido[1,2-a]benzimidazol-4-ones; Antiproliferative activity in vitro; 2-Benzylamino-1-cinnamoylbenzimidazole
• ISSN: 0014-827X; 1879-0569
• DOI: 10.1016/j.farmac.2003.12.001

A novel series of Schiff bases 1–11, the derivatives of 2-aminobenzimidazole and substituted aromatic aldehydes, has been synthesised. Compounds 1–11 reduced by NaBH 4 formed 2-benzylaminobenzimidazoles 12–21. 2-( o-Bromobenzylamino)benzimidazole ( 15) acylated by cinnamoyl chloride gave 2-( o-bromobenzylamino)-1-cinnamoylbenzimidazole ( 22). Long heating of 15 and 19 with p-nitrocinnamoyl or cinnamoyl chloride led to the formation of pyrimido[1,2-a]benzimidazol-4-ones 23 and 24. The structures of 1–24 were identified by the results of elemental analysis and their IR, 1H NMR and MS spectra. Among the compounds 1–24 evaluated for their antiproliferative activity in vitro, 16, 19, 20 and 22 exhibited cytotoxic activity against the cells of human cancer cell lines, namely SW707 (rectal), HCV29T (bladder), A549 (lung) and T47D (breast cancer).