2-Phenyl substituted Benzimidazole derivatives: Design, synthesis, and evaluation of their antiproliferative and antimicrobial activities

Abstract

The inability to meet the desired outcomes of anticancer treatment and decrease in treatment success of bacterial and fungal infections accelerated research in these areas. Our research group has conducted numerous studies, especially on benzimidazole ring systems' antiproliferative and antimicrobial activities. In this study, the antiproliferative activity of benzimidazole compounds was tested against A549, A498, HeLa, A375, and HepG2 cancer cell lines by MTT assay. All compounds exhibited good to potent antiproliferative activity against all tested cancer cell lines. Compounds 30 and 46 were especially active against HeLa and A375 cancer cell lines with IC 50 values in the range of 0.02-0.04 µM. In contrast, compounds 67 and 68 were active against A549 and A498 cancer cell lines with an IC 50 value of 0.08 µM. These compounds (30, 46, 67, and 68) were less toxic to normal human cells than the positive control compound methotrexate, which was screened to determine its toxicity against normal cell lines (HEK293). In the second part of the study, all compounds were tested to demonstrate their antimicrobial properties. All compounds exhibited moderate activity against all tested bacteria and fungi. However, some phenoxymethyl derivatives (69 and 74) were most active against Candida (<3.90 µg/mL).

Facile Synthesis of Benzimidazoles via Oxidative Cyclization of Acyclic Monoterpene Aldehyde with Diamines: Studies on Antimicrobial and in Vivo Evaluation of Zebrafish

“…The other compounds (3cf, 3j-l) have little or no interaction with target protein binding residues. [32] These compounds' weak interactions with target proteins may be explained by the existence of several donor groups connected to and at various locations of these compounds. The varying orientations of attachment of different groups to the same chemistry change the capacity of these compounds to bind because the lack of these donating groups in compounds (3g-j).…”

A Review on Benzimidazole Heterocyclic Compounds: Synthesis and Their Medicinal Activity Applications

“…Ersan, Ronak Haj, et al [133] synthesized a new 2-Phenyl substituted Benzimidazole derivatives and evaluation of their biological activity as anticancer and antimicrobial.…”

“…Ersan et al 133 synthesized new 2-phenyl substituted benzimidazole derivatives and evaluated their biological activity as anticancer and antimicrobial agents (Figure 27 ). In the antimicrobial study, all compounds were tested to confirm their antimicrobial properties against gram-positive bacteria, gram-negative bacteria and fungi.…”

“…Specifically, compound 35 provided the highest inhibition area against Klebsiella pneumonia, which was 42±0.10 mm. Ersan et al 133 synthesized new 2-phenyl substituted benzimidazole derivatives and evaluated their biological activity as anticancer and antimicrobial agents (Figure 27). In the antimicrobial study, all compounds were tested to confirm…”

Exploration of Remarkably Potential Multitarget-Directed N-Alkylated-2-(substituted phenyl)-1H-benzimidazole Derivatives as Antiproliferative, Antifungal, and Antibacterial Agents

“…In the last 2 decades, the research on benzimidazole-containing antimicrobial drugs has gained the attention of many scientific groups. Ersan et al reported that 2-(benzyl/phenylethyl/phenoxymethyl) benzimidazole derivatives showed promising antimicrobial effects against Gram-positive bacteria and fungi but relatively low effects against Gram-negative bacteria . N-Substituted benzimidazoles 6 and 7 (Figure ) effectively inhibited the growth of methicillin-resistant Staphylococcus aureus MRSA ATCC4330 and USA 300, respectively, exhibiting minimal inhibitory concentration (MIC) values up to 4 μg mL –1 , and chemical substance 7 was identified to be bactericidal.…”