Recent achievements in the synthesis of benzimidazole derivatives

Chung, Nguyen Thi; Dung, Vo Cong; Duc, Dau Xuan

doi:10.1039/d3ra05960j

Cited by 8 publications

(2 citation statements)

References 211 publications

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“…In this way, the benzimidazole (1H-benzimidazole or 1,3-Benzodiazole) scaffold is a privileged structure in new drug design and discovery; it is a nitrogen-containing heterocyclic compound consisting of benzene and imidazole rings, which have gained significance in the field of medicinal chemistry due to their extensive range of pharmacological activities, such as antibacterial, anti-inflammatory, antiviral and antiprotozoal, among others [19]. However, the antiprotozoal properties of this group have not been extensively studied.…”

Section: Introductionmentioning

confidence: 99%

Effect of Trichomonacide 6-Nitro-1H-benzimidazole Derivative Compounds on Expression Level of Metabolic Genes in Trichomonas vaginalis

Gutiérrez-Cardona,

Calderón-Jaimes,

Ortega-Cuellar

et al. 2024

IJMS

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The parasite Trichomonas vaginalis is the etiologic agent of trichomoniasis, the most common non-viral sexually transmitted disease worldwide. This infection often remains asymptomatic and is related to several health complications. The traditional treatment for trichomoniasis is the use of drugs of the 5-nitroimidazole family, such as metronidazole; however, scientific reports indicate an increasing number of drug-resistant strains. Benzimidazole derivatives could offer an alternative in the search for new anti-trichomonas drugs. In this sense, two attractive candidates are the compounds O2N-BZM7 and O2N-BZM9 (1H-benzimidazole derivatives), since, through in vitro tests, they have shown a higher trichomonacide activity. In this study, we determined the effect on the expression level of metabolic genes in T. vaginalis. The results show that genes involved in redox balance (NADHOX, G6PD::6PGL) are overexpressed, as well as the gene that participates in the first reaction of glycolysis (CK); on the other hand, structural genes such as ACT and TUB are decreased in expression in trophozoites treated with the compound O2N-BZM9, which would probably affect its morphology, motility and virulence. These results align with the trichomonacidal activity of the compounds, with benzimidazole O2N-BZM9 being the most potent, with an IC50 value of 4.8 μM. These results are promising for potential future therapeutic applications.

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Section: Introductionmentioning

confidence: 99%

Effect of Trichomonacide 6-Nitro-1H-benzimidazole Derivative Compounds on Expression Level of Metabolic Genes in Trichomonas vaginalis

Gutiérrez-Cardona,

Calderón-Jaimes,

Ortega-Cuellar

et al. 2024

IJMS

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“…Consequently, the development of synthetic methods for the preparation of functionalized benzimidazoles has gained notable attention. A common reaction mechanism used to access 1,2-disubstituted benzimidazole compounds is through a Lewis acid- or Brønsted-mediated condensation of a 1,2-diaminoarene with a carboxylic acid. , Recently, the functionalization of sp 3 -C–H bonds to directly form a new C–N bond is emerging as an attractive method in synthesis because of its step-efficiency to stitch in functionality with minimal functional group changes . In 2019, Mal and co-workers developed an intramolecular C–H amination reaction using 10 mol % PhI and m -CPBA to construct the benzimidazole scaffold 5 (Scheme ).…”

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confidence: 99%

Iodine(III)-Catalyzed Oxidative Cyclization of Aryl Amines to Construct N-Alkylbenzimidazoles

White,

Cazares,

Gonzalez-Cortes

et al. 2024

J. Org. Chem.

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An I(III)-catalyzed oxidative cyclization reaction using selectfluor as the oxidant was developed that converts ortho-substituted anilines to benzimidazoles. The mild reaction requires as little as 0.5 mol % of iodobenzene, and its scope is broad: electron-withdrawing or electronreleasing groups on the aniline portion are tolerated, and cyclic or acyclic N-alkylamines are permitted as ortho-substituents. Preliminary mechanistic investigations suggest that benzimidazole formation occurs via cationic reactive intermediates, and an intramolecular kinetic isotope effect of 1.98 ± 0.05 was measured.

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Synthesis of Substituted Benzimidazoles and Benzoxazoles by Iron‐catalysed Reductive Carbonylation of Aryl Iodides

Markandeya,

Lakshmi,

Sridhar

et al. 2024

ChemistrySelect

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This work describes a novel iron‐catalysed approach for the synthesis of aryl‐substituted benzimidazoles and benzoxazoles. The methodology employs reductive carbonylation using readily available aryl iodides and aryl amines as precursors, with carbon monoxide serving as the efficient carbonyl source. The reaction proceeds under mild conditions with the addition of hydrosilanes and bases. Notably, aryl aldehydes are generated in situ from the aryl iodides, which subsequently react with o‐phenylenediamine or 2‐aminophenol to afford the desired products in high yields. The structures of the synthesized benzimidazoles and benzoxazoles were confirmed using 1H and 13C NMR spectroscopy and mass spectrometry.

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Recent achievements in the synthesis of benzimidazole derivatives

Abstract: This article gives a comprehensive review on the synthesis of benzimidazoles including reaction mechanisms and a brief description of biological application of benzimidazole derivatives by summarizing recent studies.

Cited by 8 publications

References 211 publications

Effect of Trichomonacide 6-Nitro-1H-benzimidazole Derivative Compounds on Expression Level of Metabolic Genes in Trichomonas vaginalis

Effect of Trichomonacide 6-Nitro-1H-benzimidazole Derivative Compounds on Expression Level of Metabolic Genes in Trichomonas vaginalis

Iodine(III)-Catalyzed Oxidative Cyclization of Aryl Amines to Construct N-Alkylbenzimidazoles

Synthesis of Substituted Benzimidazoles and Benzoxazoles by Iron‐catalysed Reductive Carbonylation of Aryl Iodides

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