Synthesis, antioxidative and antiproliferative activity of methoxy amidino substituted benzamides and benzimidazoles

Abstract

Within this manuscript the synthesis and potential antioxidative and antiproliferative activity of novel methoxy amidino substituted bezamides 6–17 and benzimidazoles 23–28 and 32–35 is presented. Their antioxidative potency has been evaluated by in vitro spectrophotometric assays and preliminary structure–activity relationships among the synthesized compounds are discussed. The compound 28 bearing three methoxy groups on a phenyl ring and imidazolinyl amidine group on benzimidazole nuclei directly attached to the phenyl ring exhibited the most prominent reducing activity as well as free-radical scavenging activity. Furthermore all novel compounds were tested against three human cell lines: HCT 116 (colon carcinoma), H 460 (lung carcinoma) and MCF-7 (breast carcinoma). The most prominent antiproliferative effect in the single-digit micromolar range was observed for compound 33 on MCF-7 (IC50 = 9 µM) cell line, comparable to the standard etoposide.