Synthetic approaches to benzimidazoles from o-phenylenediamine: A literature review

Alaqeel, Shatha Ibrahim

doi:10.1016/j.jscs.2016.08.001

Cited by 167 publications

(98 citation statements)

References 13 publications

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“…However, oxidation products of Fer‐1 have not been identified experimentally. o ‐Phenylenediamine groups can also react with a carboxylic acids or aldehydes through ring closure to form benzimidazoles . Further, both fungal and mammalian cells produce nitric oxide (NO), and o ‐phenylenediamines react with NO to form benzotriazoles (Scheme S2) .…”

Section: Resultsmentioning

confidence: 99%

Antifungal Activity of the Lipophilic Antioxidant Ferrostatin‐1

et al. 2017

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Ferrostatin-1 (Fer-1) is a lipophilic antioxidant that effectively blocks ferroptosis, a distinct non-apoptotic form of cell death caused by lipid peroxidation. During many infections, both pathogens and host cells are subjected to oxidative stress, but the occurrence of ferroptosis had not been investigated. We examined ferroptosis in macrophages infected with the pathogenic yeast Histoplasma capsulatum. Unexpectedly, Fer-1 not only reduced the death of macrophages infected in vitro, but inhibited the growth of H. capsulatum and related species Paracoccidioides lutzii and Blastomyces dermatitidis at concentrations under 10 μm. Other antioxidant ferroptosis inhibitors, including liproxstatin-1, did not prevent fungal growth or reduce macrophage death. Structural analysis revealed a potential similarity of Fer-1 to inhibitors of fungal sterol synthesis, and ergosterol content of H. capsulatum decreased more than twofold after incubation with Fer-1. Strikingly, additional Fer-1 analogues with slight differences from Fer-1 had limited impact on fungal growth. In conclusion, the ferroptosis inhibitor Fer-1 has unexpected antifungal potency distinct from its antiferroptotic activity.

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Section: Resultsmentioning

confidence: 99%

Antifungal Activity of the Lipophilic Antioxidant Ferrostatin‐1

et al. 2017

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“…1) 28 . The 2-(thophen-2-yl)-1-((thiophen-2-yl) methyl)-1 H -benzo [d] imidazole was than treated with titanium (IV) isobutoxide (C 16 H 36 O 4 Ti) in an autoclave at 150 °C using DMF as the reaction media.…”

Section: Resultsmentioning

confidence: 99%

Fixation of carbon dioxide into dimethyl carbonate over titanium-based zeolitic thiophene-benzimidazolate framework

Verma

Baig

Nadagouda

et al. 2017

Sci Rep

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“…The biological implication is because of the proximity with structure of purines, and applicative importance is ascertained by their abundance in majority of bioactive molecules. However, the existence of an enormous number of this motif, associated to these applications, has led to a spectrum of protocols for its synthesis in the last decade .…”

Section: Introductionmentioning

confidence: 99%

“…The key to synthesize benzimidazole nucleus includes oxidative coupling of o ‐phenylenediamines with various aldehydes, carboxylic acids, alcohols, amines, esters, and oxime derivatives, in the presence of different reagents, at elevated temperatures (Fig. ).…”

Section: Introductionmentioning

confidence: 99%

Recent Trends in the Synthesis of Benzimidazoles From o‐Phenylenediamine via Nanoparticles and Green Strategies Using Transition Metal Catalysts

Singhal

Khanna

Panda

et al. 2019

Journal of Heterocyclic Chem

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Benzimidazole is a heterocyclic moiety of immense importance as it acts as a primary “biolinker” in diverse synthetic routes to obtain bioactive compounds. Substituted benzimidazoles are known to possess a varied range of pharmacological applications, namely, anti‐cancer, anti‐diabetic, anti‐inflammatory, and antiviral like anti‐HIV and anti‐fungal. A number of reviews covering the important aspects of benzimidazoles such as pharmacological activities, SAR studies, and well‐known methods of synthesis have appeared in the literature. However, green synthetic methods particularly using transition metal (TM) catalysts and their nanoparticles, although being more viable and extensively applied by researchers in the present scenario, have not been exclusively and expansively reviewed. Besides this, the vital precursors required for knitting the skeleton of benzimidazole are mainly o‐aryldiamines. The conventional synthesis generally involved the condensation of these diamines with carbonyl/carboxylic acid derivatives either via high temperature heating or via adding strong acids, mostly resulting in poor yields or mixtures. However, recent trends are replacing these conditions by mild and green conditions through TM catalysts. Therefore, the current review emphasizes on the recent trends adopted in the synthesis of benzimidazoles using condensation reaction of o‐phenylenediamines and various aldehydes/ester/amide/alcohols with TM in a catalytic role in nanoform and under environmentally benign green conditions.

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Synthetic approaches to benzimidazoles from o-phenylenediamine: A literature review

Cited by 167 publications

References 13 publications

Antifungal Activity of the Lipophilic Antioxidant Ferrostatin‐1

Antifungal Activity of the Lipophilic Antioxidant Ferrostatin‐1

Fixation of carbon dioxide into dimethyl carbonate over titanium-based zeolitic thiophene-benzimidazolate framework

Recent Trends in the Synthesis of Benzimidazoles From o‐Phenylenediamine via Nanoparticles and Green Strategies Using Transition Metal Catalysts

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