Synthesis of new 1,2,3-triazole linked benzimidazolidinone: Single crystal X-ray structure, biological activities evaluation and molecular docking studies

Al-Ghulikah, Hanan A.; Ghabi, Ameni; Haouas, Amel; Mtiraoui, Hasan; Jeanneau, Erwann; Msaddek, Moncef

doi:10.1016/j.arabjc.2023.104566

Cited by 6 publications

(3 citation statements)

References 51 publications

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“…The target protein (PDB ID 1T69) was used as a molecular target. Based on the evaluation process, the docking modules perfectly docked 70–80% of the ligands [ 15 , 16 , 17 , 18 ]. The Molecular Operating Environment (MOE 2016) was employed for the molecular docking analysis of the compounds based on the 1,2,3-triazole moiety [ 19 , 20 , 21 ].…”

Section: Resultsmentioning

confidence: 99%

Designing Click One-Pot Synthesis and Antidiabetic Studies of 1,2,3-Triazole Derivatives

et al. 2023

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In the present study, a new series of 1,2,3-triazole derivatives was synthesized via a click one-pot reaction. The synthesized compounds were found to be active during molecular docking studies against targeted protein 1T69 by using the Molecular Operating Environment (MOE) software. The designed and synthesized compounds were characterized by using FT-IR, 1H-NMR and LC-MS spectra. The synthesized triazole moieties were further screened for their α-amylase and α-glucosidase inhibitory activities. The preliminary activity analysis revealed that all the compounds showed good inhibition activity, ranging from moderate to high depending upon their structures and concentrations and compared to the standard drug acarbose. Both in silico and in vitro analysis indicated that the synthesized triazole molecules are potent for DM type-II. Out of all the compounds, compound K-1 showed the maximum antidiabetic activity with 87.01% and 99.17% inhibition at 800 µg/mL in the α-amylase and α-glucosidase inhibition assays, respectively. Therefore these triazoles may be further used as promising molecules for development of antidiabetic compounds.

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Section: Resultsmentioning

confidence: 99%

Designing Click One-Pot Synthesis and Antidiabetic Studies of 1,2,3-Triazole Derivatives

et al. 2023

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“…Heterocyclic compounds comprising the benzimidazolone fragment have attracted interest due to their remarkable usefulness in various therapeutic applications. Extensive research has revealed several pharmacological and biological properties associated with these compounds, including antiproliferative (Guillon et al, 2022), antibacterial (Al-Ghulikah et al, 2023;Saber et al, 2020), anticancer (Dimov et al, 2021) and antiviral (Ferro et al, 2017) activities.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis, calculations of intermolecular interaction energies and energy frameworks and the DFT-optimized molecular structure of 1-[(1-butyl-1H-1,2,3-triazol-4-yl)methyl]-3-(prop-1-en-2-yl)-1H-benzimidazol-2-one

El Atrassi,

Zouhair,

Blacque

et al. 2024

Acta Cryst E

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The benzimidazole entity of the title molecule, C17H21N5O, is almost planar (r.m.s. deviation = 0.0262 Å). In the crystal, bifurcated C—H...O hydrogen bonds link individual molecules into layers extending parallel to the ac plane. Two weak C—H...π(ring) interactions may also be effective in the stabilization of the crystal structure. Hirshfeld surface analysis of the crystal structure reveals that the most important contributions for the crystal packing are from H...H (57.9%), H...C/C...H (18.1%) and H...O/O...H (14.9%) interactions. Hydrogen bonding and van der Waals interactions are the most dominant forces in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the stabilization of the title compound is dominated via dispersion energy contributions. The molecular structure optimized by density functional theory (DFT) at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state.

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“…Using the click reaction, Al‐Ghulikah et al. (2023) synthesized a set of 1,2,3‐triazole‐benzimidazolidinone hybrid derivatives from a reaction between a terminal alkyne‐containing benzimidazolidinone moiety and various aryl azides reacted. The strongest inhibition activity was related to compound O′ against A. brasiliensis and A. fumigatus , with ZIs of 27 and 26 mm, respectively, better than nystatin (ZI ≤ 25 mm).…”

Section: Antifungal 123‐triazole Hybridsmentioning

confidence: 99%

Click chemistry beyond metal‐catalyzed cycloaddition as a remarkable tool for green chemical synthesis of antifungal medications

Tahghighi,

Azerang

2024

Chem Biol Drug Des

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Click chemistry is widely used for the efficient synthesis of 1,4‐disubstituted‐1,2,3‐triazole, a well‐known scaffold with widespread biological activity in the pharmaceutical sciences. In recent years, this magic ring has attracted the attention of scientists for its potential in designing and synthesizing new antifungal agents. Despite scientific and medical advances, fungal infections still account for more than 1.5 million deaths globally per year, especially in people with compromised immune function. This increasing trend is definitely related to a raise in the incidence of fungal infections and prevalence of antifungal drug resistance. In this condition, an urgent need for new alternative antifungals is undeniable. By focusing on the main aspects of reaction conditions in click chemistry, this review was conducted to classify antifungal 1,4‐disubstituted‐1,2,3‐triazole hybrids based on their chemical structures and introduce the most effective triazole antifungal derivatives. It was notable that in all reactions studied, Cu(I) catalysts generated in situ by the reduction in Cu(II) salts or used copper(I) salts directly, as well as mixed solvents of t‐BuOH/H2O and DMF/H2O had most application in the synthesis of triazole ring. The most effective antifungal activity was also observed in fluconazole analogs containing 1,2,3‐triazole moiety and benzo‐fused five/six‐membered heterocyclic conjugates with a 1,2,3‐triazole ring, even with better activity than fluconazole. The findings of structure–activity relationship and molecular docking of antifungal derivatives synthesized with copper‐catalyzed azide–alkyne cycloaddition (CuAAC) could offer medicinal chemistry scientists valuable data on designing and synthesizing novel triazole antifungals with more potent biological activities in their future research.

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Synthesis of new 1,2,3-triazole linked benzimidazolidinone: Single crystal X-ray structure, biological activities evaluation and molecular docking studies

Cited by 6 publications

References 51 publications

Designing Click One-Pot Synthesis and Antidiabetic Studies of 1,2,3-Triazole Derivatives

Designing Click One-Pot Synthesis and Antidiabetic Studies of 1,2,3-Triazole Derivatives

Crystal structure, Hirshfeld surface analysis, calculations of intermolecular interaction energies and energy frameworks and the DFT-optimized molecular structure of 1-[(1-butyl-1H-1,2,3-triazol-4-yl)methyl]-3-(prop-1-en-2-yl)-1H-benzimidazol-2-one

Click chemistry beyond metal‐catalyzed cycloaddition as a remarkable tool for green chemical synthesis of antifungal medications

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