Synthesis of Certain 2-Substituted-1<i>H</i>-benzimidazole Derivatives as Antimicrobial and Cytotoxic Agents

Abstract

A series of 2-substituted-1H-benzimidazole derivatives were synthesized and evaluated for antimicrobial, antifungal and cytotoxic activities. The results showed that all tested compounds showed potent antimicrobial activity against some species of Gram-negative bacteria (Pseudomonas aeruginosa, Escherichia coli, Salmonella typhi) and fungi (Candida albicans) with minimum inhibitory concentrations (MICs) lower than 0.016 µg/mL. In contrast, all tested compounds were inactive against Staphylococcus aureus (Gram-positive bacterium). The final targets were also tested for their antitumor activity in vitro on cervical carcinoma (HeLa) cell line. Eight of the test compounds displayed more potent cytotoxic effect than doxorubicin at nanomolar concentrations. Compounds 2c and 3c exerted the strongest cytoyoxic effect with IC 50 15 and 13 nM, respectively.

CuI-Catalyzed C–N Bond Formation and Cleavage for the Synthesis of Benzimidazo[1,2-a]quinazoline Derivatives

“…In addition, benzimidazoles are also useful heterocyclic molecules, and the potential therapeutic applications of their derivatives include antimicrobial, antitumor, and antibacterial activities . They are also used as inhibitors of PI3-kinase and the potent antistaphylococcal agents with dual inhibitory mechanisms against DNA gyrase .…”

Synthesis, characterization, biological evaluation and molecular docking studies of 2-(1H-benzo[d]imidazol-2-ylthio)-N-(substituted 4-oxothiazolidin-3-yl) acetamides

“…All the synthesized derivatives were docked onto the crystal structure of cyclin-dependent kinase 8 (CDK8) using sequential docking procedure on the crystal structure [PDB ID: 5FGK] retrieved from the protein data bank (PDB) [ 16 ]. The CDK8 protein structure was optimized using protein preparation wizard by removing the water molecules, hetero-atoms and co-factors.…”

“…Benzimidazole is a heterocyclic moiety of immense importance in drug discovery [ 15 ]. Moreover, the structural analogy of benzimidazole to the biological nucleotides enable it to interact with the biopolymers while enriching it with vast number of therapeutic activities including anticancer, antibacterial, antifungal, antiviral, anthelmintic, antihypertensive, antioxidant and anticoagulant activities [ 16 ].…”

Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction

“…1e,f This article details studies directed toward the preparation of functionalized quinoxalines that constitute an important class of nitrogen containing heterocycles utilized in many sectors of the chemical industry. 8,9 Unfortunately, reported methods to synthesize quinoxalines suffer from various drawbacks, most noticeably harsh reaction conditions and use of toxic metals. 10 The most widely used protocol 11 for quinoxaline preparation is limited to the trivial condensation of 1,2-diamines with 1,2-dicarbonyl reagents or acyl halides; a strategy allowing only two points of diversity.…”