This study reports a simple process to synthesize and separate of 2-(substituted-phenyl) benzimidazole derivatives with high yield and efficiency. Specifically, by reacting ortho-phenylenediamines with benzaldehydes using sodium metabisulphite as an oxidation agent in a mixture of solvent under mild condition,twenty-three compounds of benzimidazoles were obtained and separated easily using hexane and water to wash, respectively. The structure of all obtained compounds was identified by FTIR, NMR and HRMS. The SAR analysis of synthesized benzimidazoles on human lung (A549), breast (MDA-MB-231) andprostate (PC3) cancer cell lines showed that the presence of methyl group at 5(6)-position on benzimidazole scaffold was a contributing factor influencing the anticancer activity. The presence of electron-donating groups (OH, OMe, –NMe2, –O–CH2–C6H5) also caused significant increase of anticancer activity, while thepresence of electron-withdrawing groups (–NO2, –CF3) on the phenyl group at 2-position of benzimidazole ring decreased the ability of inhibition of synthesized benzimidazoles. The compounds 2f and 2g displayed the significant anticancer activity on both A549 and PC3 cell lines.
Volume 132, 2020
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