Simple, Mild, and Highly Efficient Synthesis of 2-Substituted Benzimidazoles and Bisbenzimidazoles

Eren, Bi̇lge; Bekdemi̇r, Yunus

doi:10.5935/0100-4042.20140096

Cited by 14 publications

(8 citation statements)

References 29 publications

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“…Then, o -phenylene diamine readily condenses with this reactive adduct to form 2-substituted benzimidazole. Use of metabisulfite has several advantages, including short reaction time, simple workup, easy purification of products, and mild reaction conditions. , Structures of synthetic compounds were identified by spectroscopic techniques such as UV, IR, electron ionization mass spectroscopy (EI-MS), high-resolution electron impact mass spectrometry (HREI-MS), 1 H NMR, and 13 C NMR. Structures of compounds 1 and 6 – 8 − are already known, while the rest are new.…”

Section: Resultsmentioning

confidence: 99%

Substituted Benzimidazole Analogues as Potential α-Amylase Inhibitors and Radical Scavengers

et al. 2021

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Benzimidazole scaffolds are known to have a diverse range of biological activities and found to be antidiabetic and antioxidant. In this study, a variety of arylated benzimidazoles 1–31 were synthesized. Except for compounds 1, 6, 7, and 8, all are new derivatives. All compounds were screened for α-amylase inhibitory, 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities. In vitro screening results revealed that all molecules demonstrated significant α-amylase inhibition with IC50 values of 1.86 ± 0.08 to 3.16 ± 0.31 μM as compared to standard acarbose (IC50 = 1.46 ± 0.26 μM). However, compounds showed significant ABTS and DPPH radical scavenging potentials with IC50 values in the range of 1.37 ± 0.21 to 4.00 ± 0.10 μM for ABTS and 1.36 ± 0.09 to 3.60 ± 0.20 μM for DPPH radical scavenging activities when compared to ascorbic acid with IC50 values of 0.72 ± 0.21 and 0.73 ± 0.05 μM for ABTS and DPPH radical scavenging potentials, respectively. Structure–activity relationship (SAR) was established after critical analysis of varying substitution effects on α-amylase inhibitory and radical scavenging (ABTS and DPPH) potentials. However, molecular docking was also performed to figure out the active participation of different groups of synthetic molecules during binding with the active pocket of the α-amylase enzyme.

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Section: Resultsmentioning

confidence: 99%

Substituted Benzimidazole Analogues as Potential α-Amylase Inhibitors and Radical Scavengers

et al. 2021

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“…The literature reports several approaches for the synthesis of 2‐substituted benzimidazoles, including the condensation of o ‐phenylenediamine derivatives with carboxylic acids or their derivatives under strongly acidic conditions or with aldehyde/alcohol in the presence of different oxidizing agents or catalysts, or performing microwave‐assisted procedures . As such, two previous studies have described distinct methods for obtaining the 2‐pyridine‐substituted benzimidazole dppb.…”

Section: Resultsmentioning

confidence: 99%

Dinuclear copper(II) complex with a benzimidazole derivative: Crystal structure, theoretical calculations, and cytotoxic activity

Cassemiro

Santos

Oliveira

et al. 2020

Applied Organom Chemis

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This work describes a facile synthesis of 5,6‐dimethyl‐2‐(pyridin‐2‐yl)‐1‐[(pyridin‐2‐yl)methyl]‐1H‐benzimidazole (dppb) and the preparation of a dinuclear copper(II) complex bearing this ligand in a ring‐like conformation of formula [Cu(dppb)(acn)ClO4]2(ClO4)2·4acn (1), where acn represents acetonitrile. The crystal structure of the complex was determined by single‐crystal X‐ray diffraction experiment, which showed that dppb acts as a bridge in 1 due to its bidentate–monodentate μ‐κ2NN′:κN″coordination mode, and the coordination sphere of each metal center is completed by one acn molecule and one perchlorate ion. The structure of dinuclear copper(II) complex is symmetric and the two square–pyramidal copper(II) centers are separated by 5.381(1) Å. The geometry optimization, electronic structure, and vibrational spectrum of the [Cu(dppb)(acn)ClO4]22+ cation were calculated using the density functional theory method. The geometrical parameters obtained theoretically were remarkably similar to those observed in the crystal structure of 1 and the calculated vibrational frequencies are in satisfactory coherence with experimental data. In solution, the prepared complex can bind to DNA (Kb = 1.43 × 105 M−1) and inhibit the growth of a human chronic myelogenous leukemia cell line (K562) in a concentration‐dependent manner; importantly, it is almost four times more active than the corresponding free benzimidazole.

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“…The synthetic route of PFCZ‐IM is illustrated in Scheme 1. Compounds 1 – 4 and 6 and the carbazole‐fluorene copolymer without the side chain (PFCZ) were synthesized according to reported procedures 29–34 …”

Section: Methodsmentioning

confidence: 99%

A poly(carbazole‐alt‐fluorene) π‐conjugated polymer bearing thiophenyl benzimidazole: synthesis, characterization and fluorescence recognition of metal ions and cysteine

Liu

Wei

et al. 2021

Polymer International

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A novel conjugated polymer PFCZ‐IM containing 2‐(thiophen‐2‐yl)‐1H‐benzo[d]imidazole units was synthesized and characterized. The basic photophysical properties of the polymer and its fluorescence recognition behaviors toward metal ions and amino acids were investigated. In the study of the response of metal ions, PFCZ‐IM had high sensitivity to Fe3+, Ag+ and Cu2+, which significantly quenched the fluorescence of the polymer. The binding of the 2‐(thiophen‐2‐yl)‐1H‐benzo[d]imidazole moiety to Cu2+ was investigated by density functional theory calculation. Interestingly, [PFCZ‐IM‐Cu2+] also exhibited outstanding characteristics of fluorescence ‘turn on’ in the presence of cysteine (Cys), as the interaction between Cu2+ and Cys caused the polymer to dissociate from the complex. In particular, addition of 30 μmol L–1 of Cys can increase the Cu2+‐quenching fluorescence of PFCZ‐IM by 34.8 times with short response time, demonstrating that [PFCZ‐IM‐Cu2+] has tremendous potential in the actual detection of Cys. This polymer is expected to be utilized for dual fluorescence detection of specific metal ions and Cys. © 2021 Society of Industrial Chemistry.

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Simple, Mild, and Highly Efficient Synthesis of 2-Substituted Benzimidazoles and Bisbenzimidazoles

Cited by 14 publications

References 29 publications

Substituted Benzimidazole Analogues as Potential α-Amylase Inhibitors and Radical Scavengers

Substituted Benzimidazole Analogues as Potential α-Amylase Inhibitors and Radical Scavengers

Dinuclear copper(II) complex with a benzimidazole derivative: Crystal structure, theoretical calculations, and cytotoxic activity

A poly(carbazole‐alt‐fluorene) π‐conjugated polymer bearing thiophenyl benzimidazole: synthesis, characterization and fluorescence recognition of metal ions and cysteine

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