Synthesis and insight into the structure–activity relationships of 2-phenylbenzimidazoles as prospective anticancer agents

Huynh, Thi-Kim-Chi; Nguyen, Thi-Hong-An; Nguyen, Thi-Cam-Thu; Hoang, Thai

doi:10.1039/d0ra02282a

Cited by 15 publications

(8 citation statements)

References 33 publications

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“…Unfortunately, the reaction was unsuccessful in providing the expected product 7 and the imidazole 6 was obtained instead (Scheme 1). An earlier report 28 revealed that the use of meta-/para -substituted chalcones gives benzodiazepines rather than imidazoles. 29 Owing to the presence of the o -benzyl unit in chalcone 3m , steric hindrance may be the reason for the failure to obtain benzodiazepine 7 .…”

Section: Resultsmentioning

confidence: 99%

An expedient, one-pot, stepwise sequential approach for the regioselective synthesis of pyrazolines

Ganesan

Muniraj

Doble

2020

Journal of Chemical Research

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An efficient approach for the synthesis of pyrazoline/pyrazole-tethered pyridinyl methanones is described via a one-pot, stepwise, sequential methodology using chalcones and pyridine-4-carbohydrazide as substrates through a Michael addition followed by cyclization. The reaction proceeds via a catalyst-, solvent-, work-up-, and column-chromatography-free method under melt conditions to provide the pyrazolines in short reaction times with high atom efficiency.

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Section: Resultsmentioning

confidence: 99%

An expedient, one-pot, stepwise sequential approach for the regioselective synthesis of pyrazolines

Ganesan

Muniraj

Doble

2020

Journal of Chemical Research

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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%

“…The benzimidazole derivatives shown in scheme 1 were synthesized by a condensation reaction between o-phenylenediamine and benzaldehyde in the presence of Na 2 S 2 O 5 as an oxidation agent [31]. The yields obtained after purification ranged from 70% to 90%.…”

Section: Synthesis and Characterizationmentioning

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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“…10 Huynh and coworkers synthesized several new derivatives of 2-phenylbenzimidazole with a various range of substituents on the C-5, C-2, and C-6 positions of 2-phenylbenzimidazole with the condensation of o-phenylenediamines and different aldehydes and afterwards to illustrate their structure-activity relationship (SAR) upon three cancer cell lines:PC3, MDA-MB-231and A54. 11 On the other hand, quantitative structure-activity relationship studies have obtained a fundamental position within medicine chemistry. In QSAR analysis, one or more molecular descriptors are described to the molecular activity using statistical analysis.…”

Section: Introductionmentioning

confidence: 99%

Density functional theory calculations and molecular docking of 2-phenylbenzimidazoles with estrogen receptor for quantitative structure-activity relationship studies

Mahani

Mohammadi

Anjomshoa

2022

JSCS

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Benzimidazole derivatives, especially 2-phenylbenzimidazole with various substituents on the C-5, C-2, and C-6 positions, are so important in pharmaceutical chemistry. Multiple linear regression was applied to predict the activity of 27 novel 2-phenylbenzimidazole derivatives as anticancer agents. At first, we effort to create a QSAR model for a selected series of novel 2-phenyl-benzimidazole with density functional theory and molecular docking descriptors. Then, we tried to investigate the nature of the interactions between 2-pheny-lbenzimidazole derivatives and the Estrogen Receptor by using the molecular docking method. Six descriptors of MATS4e, GATS5e, R6v, R1v+, dipole moment, and torsional free energy were selected for modelling. Due to docking results, increasing the binding energy, and decreasing the dipole moment could be increasing of inhibitor activity.

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Synthesis and insight into the structure–activity relationships of 2-phenylbenzimidazoles as prospective anticancer agents

Abstract: Three series of 2-phenylbenzimidazoles obtained under simple and convenient pathways, were used to elucidate their SARs against three cancer cell lines: A549, MDA-MB-231 and PC3.

Cited by 15 publications

References 33 publications

An expedient, one-pot, stepwise sequential approach for the regioselective synthesis of pyrazolines

An expedient, one-pot, stepwise sequential approach for the regioselective synthesis of pyrazolines

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

Density functional theory calculations and molecular docking of 2-phenylbenzimidazoles with estrogen receptor for quantitative structure-activity relationship studies

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