A facile and efficient synthesis of benzimidazole as potential anticancer agents

Huynh, Thi-Kim-Chi; Nguyen, Thi-Hong-An; Tran, Ngoc-Hoang-Son; Nguyen, Thanh-Danh; Hoang, Thi-Kim-Dung

doi:10.1007/s12039-020-01783-4

Cited by 20 publications

(11 citation statements)

References 12 publications

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“…Possible pathway 2: It can also be assumed that the reaction is triggered by disproportionation of the starting pyrrolecarbaldehyde 1 (the Cannizzaro type reaction [17]) to furnish carboxylic acid F and alcohol G, which further interact with o-PDA. In the case of carboxylic acid, the process involves the formation of product 3 similar to the reaction with aldehyde (such reactions are well known [18][19][20]). In alcohol G, the substitution at the hydroxyl group occurs with participation the o-PDA amino group to deliver the intermediate H, followed by intramolecular addition of the second amino group at the allene producing a 9-membered ring I.…”

Section: Resultsmentioning

confidence: 99%

Solvent Moisture-Controlled Self-Assembly of Fused Benzoimidazopyrrolopyrazines with Different Ring’s Interposition

Martynovskaya¹,

Budaev²,

Ushakov³

et al. 2022

Molecules

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This article shows that two extremely important families of fused heterocyclic assemblies, namely 6-methylbenzo[4,5]imidazo[1,2-a]pyrrolo[2,1-c]pyrazine and 5a-methyl-5a,6-dihydro-5H,12H-benzo[4,5]imidazo[1,2-a]pyrrolo[1,2-d]pyrazine, can be synthesized from only two available building blocks (N-allenylpyrrole-2-carbaldehyde and o-phenylenediamine) by controlling only one reaction parameter (water content of the medium). It should be emphasized that the latter class of compounds (with an a/d arrangement) is previously unknown. If the allene group is introduced not into the starting compound, but during the reaction (in superbase media), a heterocyclic ensemble, 5-methylbenzo[4,5]imidazo[1,2-a]pyrrolo[2,1-c]pyrazines, with a different position of the methyl group is formed.

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Section: Resultsmentioning

confidence: 99%

Solvent Moisture-Controlled Self-Assembly of Fused Benzoimidazopyrrolopyrazines with Different Ring’s Interposition

Martynovskaya¹,

Budaev²,

Ushakov³

et al. 2022

Molecules

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“…The synthesis of ligands L 1 – L 5 was described in our previous reports [31,32], and for convenience of information searching, their identified characteristics are listed below.…”

Section: Methodsmentioning

confidence: 99%

Metal complexes of benzimidazole-derived as potential anti-cancer agents: synthesis, characterization, combined experimental and computational studies

Thanh¹,

Huynh²,

et al. 2022

R. Soc. open sci.

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In this study, a series of 14 Cu (II), Zn (II), Ni (II) and Ag (I) complexes containing bis-benzimidazole derivatives were successfully designed and synthesized from 2-(1 H -benzimidazole-2-yl)-phenol derivatives and corresponding metal salt solutions. The compound structures were identified by FT-IR, 1 H-NMR, powder X-ray diffraction and ESI-MS analyses, and the presence of the metal in the complexes was confirmed by ultraviolet-visible spectroscopy and ICP optical emission spectrometry. Electronic structure calculations were also carried out to describe the detailed structures in addition to the electronic absorption spectra of the ligands. The cytotoxic activity of the complexes was evaluated against three human cancer cell lines: lung (A549), breast (MDA-MB-231) and prostate (PC3) cancer cells. All complexes inhibited anti-proliferative cancer cells better than free ligands, especially Zn (II) and Ag (I) complexes, which are most sensitive to MDA-MB-231 cells. In addition, showing the growth inhibition of three cancer cell lines with IC 50 < 10.4 µM, complexes C 1 , C 3 and C 14 could be considered potential multi-targeted anti-cancer agents.

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“…The crude product was recrystallized from MeOH and Et2O to give white solid product (688.9 mg, 1.87 mmol, 60% yield 57 This compound was synthesized according to modified literature procedures. [58][59] Procedure 1: In a 200 mL round-bottom flask, o-phenylenediamine (2.1624 g, 20.00 mmol, 1.0 eq. ),…”

Section: Nn'-dimethyl-o-phenylenediaminementioning

confidence: 99%

Sensitizer-free photochemical regeneration of benzimidazoline organohydride

Matsubara

Harada

Xie

et al. 2023

Preprint

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Organohydrides are an important class of organic compounds that can provide hydride anions for chemical and biochemical reactions, as demonstrated by reduced nicotinamide adenine dinucleotide serving as an important natural redox cofactor. The coupling of hydride transfer from the organohydride to the substrate and subsequent regeneration of the organohydride from its oxidized form can realize organohydride-catalyzed reduction reactions. Depending on the structure of the organohydride, its hydridicity and ease of regeneration vary. Benzimidazoline (BIH) is one of the strongest synthetic C–H hydride donors; however, its reductive regeneration requires highly reducing conditions. In this study, we synthesized various oxidized and reduced forms of BIH derivatives with aryl groups at the 2-position and investigated their photophysical and electrochemical properties. 4-(Dimethylamino)phenyl-substituted BIH exhibited salient red-shifted absorption compared to other synthesized BIH derivatives, and visible-light-driven regeneration without using an external photosensitizer was achieved. This knowledge has significant implications for the future development of solar-energy-based catalytic photoreduction technologies that utilize organohydride regeneration strategies.

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A facile and efficient synthesis of benzimidazole as potential anticancer agents

Cited by 20 publications

References 12 publications

Solvent Moisture-Controlled Self-Assembly of Fused Benzoimidazopyrrolopyrazines with Different Ring’s Interposition

Solvent Moisture-Controlled Self-Assembly of Fused Benzoimidazopyrrolopyrazines with Different Ring’s Interposition

Metal complexes of benzimidazole-derived as potential anti-cancer agents: synthesis, characterization, combined experimental and computational studies

Sensitizer-free photochemical regeneration of benzimidazoline organohydride

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