Design, synthesis, biological evaluation and QSAR analysis of novel <i>N</i>-substituted benzimidazole derived carboxamides

Beč, Anja; Mioč, Marija; Bertoša, Branimir; Kos, Marija; Debogović, Patricia; Kralj, Marijeta; Starčević, Kristina; Hranjec, Marijana

doi:10.1080/14756366.2022.2070910

Cited by 4 publications

(7 citation statements)

References 36 publications

(40 reference statements)

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“…All the investigated benzamide derivatives were synthesized following the two synthetic procedures illustrated in reaction Schemes 1 and 2, using well-described and conventional organic synthetic methods [31]. The above-mentioned considerations prompted us to extend our previous research by introducing electron-donating groups to the nitrogen atom and hydroxy groups to the phenyl ring.…”

Section: Chemistrymentioning

confidence: 99%

“…The main precursors for the synthesis of targeted benzamides, the methoxy-substituted derivatives 1-6, were prepared by previously published synthetic procedures [31,32].…”

Section: Chemistrymentioning

confidence: 99%

“…EDC.HCl is a carbodiimide used to activate carboxylic acid for amide or ester formation. The main precursors for the synthesis of targeted benzamides, the methoxysubstituted derivatives 1-6, were prepared by previously published synthetic procedures [31,32].…”

Section: Chemistrymentioning

confidence: 99%

“…Some of the hydroxy-substituted carboxamide derivatives with potent antioxidant activity target specific pathways or molecules involved in oxidative stress without adversely affecting normal cellular processes, resulting in lower cytotoxicity [27][28][29][30]. Additionally, our intention was to study the influence of a substituent placed at the N atom of the benzimidazole core, and we synthesized N-substituted benzimidazole-2-carboxamides bearing different numbers of methoxy groups on the phenyl ring [31]. Isobutyl and methyl groups placed at the N atom had the most significant influence on the antioxidative and antiproliferative activity (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis and Biological Activity of Novel Methoxy- and Hydroxy-Substituted N-Benzimidazole-Derived Carboxamides

Beč,

Zlatić,

Banjanac

et al. 2024

Molecules

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This work presents the design, synthesis and biological activity of novel N-substituted benzimidazole carboxamides bearing either a variable number of methoxy and/or hydroxy groups. The targeted carboxamides were designed to investigate the influence of the number of methoxy and/or hydroxy groups, the type of substituent placed on the N atom of the benzimidazole core and the type of substituent placed on the benzimidazole core on biological activity. The most promising derivatives with pronounced antiproliferative activity proved to be N-methyl-substituted derivatives with hydroxyl and methoxy groups at the phenyl ring and cyano groups on the benzimidazole nuclei with selective activity against the MCF-7 cell line (IC50 = 3.1 μM). In addition, the cyano-substituted derivatives 10 and 11 showed strong antiproliferative activity against the tested cells (IC50 = 1.2–5.3 μM). Several tested compounds showed significantly improved antioxidative activity in all three methods compared to standard BHT. In addition, the antioxidative activity of 9, 10, 32 and 36 in the cells generally confirmed their antioxidant ability demonstrated in vitro. However, their antiproliferative activity was not related to their ability to inhibit oxidative stress nor to their ability to induce it. Compound 8 with two hydroxy and one methoxy group on the phenyl ring showed the strongest antibacterial activity against the Gram-positive strain E. faecalis (MIC = 8 μM).

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Section: Chemistrymentioning

confidence: 99%

“…The main precursors for the synthesis of targeted benzamides, the methoxy-substituted derivatives 1-6, were prepared by previously published synthetic procedures [31,32].…”

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis and Biological Activity of Novel Methoxy- and Hydroxy-Substituted N-Benzimidazole-Derived Carboxamides

Beč,

Zlatić,

Banjanac

et al. 2024

Molecules

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“…Machine learning has been used in a variety of fields including biology 18 and chemistry. 19 Machine learning model is constructed between experimental conditions and physical properties of materials.…”

Section: Introductionmentioning

confidence: 99%

Machine Learning Model for Predicting the Material Properties and Bone Formation Rate and Direct Inverse Analysis of the Model for New Synthesis Conditions of Bioceramics

Motojima

Shiratsuchi

Suzuki

et al. 2023

Ind. Eng. Chem. Res.

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Bioceramics, such as hydroxyapatite and β-tricalcium phosphate, are widely used in orthopedics and oral surgery because they are free in shape and size and are not harvested from patients or donors. General development of bioceramics requires a great deal of effort, a long time, and many animal experiments. Because an animal experiment takes several months and is currently regarded as an ethical problem, the number of experiments should be reduced. In this study, machine learning was applied to construct mathematical models to predict the material properties, including the porosity, compressive strength, Ca2+ dissolution rate, and bone formation rate, from the synthesis conditions and to design synthesis conditions of bioceramics with desired bone formation rates. We propose two types of models: model 1 to predict the material properties, crystallite sizes, and second selected Fourier transform infrared wavenumbers of the resulting bioceramics from the synthesis conditions, such as the starting powder conditions, and model 2 to predict the bone formation rate from the material properties, crystallite sizes, second selected Fourier transform infrared wavenumbers, and animal experimental conditions of bioceramics. Both models were constructed using Gaussian mixture regression, enabling direct inverse analysis of the models. Furthermore, by visualization of the models, the relationships among the bone formation rate, material properties, and animal experimental conditions can be understood to establish guidelines for designing the synthesis conditions. We succeeded in designing artificial bone synthesis conditions with bone formation rate exceeding existing bone formation rates.

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N-alkylbenzimidazole silver(I) complexes: Synthesis, biological evaluation and molecular docking study

Arı,

Şahin,

Üstün

et al. 2024

Polyhedron

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Design, synthesis, biological evaluation and QSAR analysis of novel N-substituted benzimidazole derived carboxamides

Cited by 4 publications

References 36 publications

Design, Synthesis and Biological Activity of Novel Methoxy- and Hydroxy-Substituted N-Benzimidazole-Derived Carboxamides

Design, Synthesis and Biological Activity of Novel Methoxy- and Hydroxy-Substituted N-Benzimidazole-Derived Carboxamides

Machine Learning Model for Predicting the Material Properties and Bone Formation Rate and Direct Inverse Analysis of the Model for New Synthesis Conditions of Bioceramics

N-alkylbenzimidazole silver(I) complexes: Synthesis, biological evaluation and molecular docking study

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