Preparation, Reactivity, and Synthetic Utility of Simple Benzotriazole Derivatives

Gérardy, Romaric; Monbaliu, Jean‐Christophe M.

doi:10.1007/7081_2015_179

Cited by 7 publications

(6 citation statements)

References 355 publications

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“…[24] Benzotriazoles can bind to biological systems' enzymes and receptors due to their structural features such as the existence of a large conjugated system and the three nitrogen atoms that enable them to form hydrogen bonds and/or other types of molecular interactions, such as π-π stacking and van der Waals forces. [25] Moreover, benzotriazole is a heterocyclic scaffold that can be easily incorporated into molecules by a variety of simple chemical reactions. Benzotriazole derivatives possess diverse biological features as choleretic, [26] antibacterial, [27][28][29][30][31] antiprotozoal, [32] antiviral, [33] antiinflammatory, [34] and antiproliferative [35][36][37] action.…”

Section: Introductionmentioning

confidence: 99%

Benzotriazole scaffold: An overview of antiproliferative potential, mechanisms of action, and structure–activity relationships

Kassab

2023

Archiv der Pharmazie

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Being an isostere of the purine nucleus, which is found in naturally occurring nucleotides like ATP and other naturally available substances, benzotriazole is not surprising for its broad-spectrum biological activity. Benzotriazole is widely used by medicinal chemists as a privileged scaffold for the identification and development of novel bioactive compounds and drug candidates. Additionally, benzotriazole is a structural motif of seven pharmaceuticals; some of these compounds are approved, commercially available medications, while others are experimental drugs still under investigation. This review highlights the defining role of benzotriazole derivatives in the search for potential anticancer agents published in the literature from 2008 to 2022; it also discusses their mechanisms of action and structure-activity relationship investigations.

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Section: Introductionmentioning

confidence: 99%

Benzotriazole scaffold: An overview of antiproliferative potential, mechanisms of action, and structure–activity relationships

Kassab

2023

Archiv der Pharmazie

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“…Среди данного класса веществ 2-гидроксинитроазобензолы занимают особое положение, так как являются исходными продуктами синтеза гетероароматических соединений, в молекуле которых аннелированы бензольный и азольный циклы. Замещенные 2Н-бензотриазолы используются как эффективные абсорберы ультрафиолетового (УФ) света, светостабилизаторы полимеров, аналитические реагенты на ряд катионов, применяются в качестве добавок для увеличения светостойкости красителей, пигментов и эмалей, для получения комплексных соединений с металлами и в других областях [1][2][3][4][5][6][7][8].…”

Section: Introductionunclassified

Structure of 2-nitro-2’-hydroxy-5’-methylazobenzene: Theoretical and spectroscopic study

Fedorova,

Lefedova,

Shlykov

2023

Fine Chem. Technol.

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Objectives. 2-Hydroxy-nitroazobenzenes comprise reagents for the synthesis of heteroaromatic compounds, in the molecules of which the benzene and azole cycles are annulated. These reagents are widely used in the production of chemical products for various industries. In particular, 2-2’-hydroxy-5’-methylphenylbenzotriazole is used as an effective photo stabilizer for polystyrene and polyethylene. A promising method for its preparation is the liquid-phase catalytic hydrogenation of 2-nitro-2'-hydroxy-5'-methylazobenzene (2NAB). The aim of the present study was to establish the structure of 2NAB in solutions of different composition.Methods. Theoretical calculations were carried out within the framework of the density functional theory at a temperature of 298.15 K for the gas phase at B3LYP/6-311++G(d, p) and M06-2X/6-311++G(d, p) levels; for hexane, 2-propanol, toluene at B3LYP/6-311++G(d, p) level using the conductor-like polarizable continuum model. An experimental study to determine the probable isomeric structure of 2NAB in various solvents, including sodium hydroxide (NaOH) and acetic acid (CH3COOH) additives, was carried out using infrared (IR) and ultraviolet (UV) spectroscopy.Results. The most probable structure of 2NAB isomers for the gas phase and a number of solvents was determined. Experimental and theoretical IR and UV spectra were obtained. The thermodynamic characteristics of the reaction of intramolecular proton transfer from –OH to –N=N– group in the gas phase were calculated.Conclusions. A comparison of the experimental and calculated results supports the conclusion that the cis-isomer should be considered most probable for the gas phase. For the studied solutions, a trans-isomer of 2NAB with hydrogen bonds formed between the hydroxyl group hydrogen and the β-nitrogen atom of the azo group of dye molecule should be considered as the most likely structure. In the studied individual and binary solvents, prototropic equilibrium is shifted towards the azo form of the dye, while intramolecular proton transfer is possible only in aqueous diethylamine and dimethylformamide solutions with additions of NaOH.

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“…54 Despite its renowned versatility, benzotriazole is not commonly used as ligand for the preparation of luminescent transition metal complexes. [55][56][57] Our research group recently exploited benzotriazole and the related heterocycle indazole as coordinating moieties in polydentate ligands applied for the preparation of luminescent Cu(I) complexes. [58][59][60] So far, the conjugation of benzotriazole in combination with a different aromatic N-donor heterocycle was not considered.…”

Section: Introductionmentioning

confidence: 99%

Visible-emitting Cu(i) complexes with N-functionalized benzotriazole-based ligands

Castro

Bortoluzzi

2022

New J. Chem.

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Preparation, Reactivity, and Synthetic Utility of Simple Benzotriazole Derivatives

Cited by 7 publications

References 355 publications

Benzotriazole scaffold: An overview of antiproliferative potential, mechanisms of action, and structure–activity relationships

Benzotriazole scaffold: An overview of antiproliferative potential, mechanisms of action, and structure–activity relationships

Structure of 2-nitro-2’-hydroxy-5’-methylazobenzene: Theoretical and spectroscopic study

Visible-emitting Cu(i) complexes with N-functionalized benzotriazole-based ligands

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