Benzotriazole: Much More Than Just Synthetic Heterocyclic Chemistry

Bajaj, Kiran; Sakhuja, Rajeev

doi:10.1007/7081_2015_198

Cited by 15 publications

(10 citation statements)

References 101 publications

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“…This observation may arise from the higher lipophilicity of the benzotriazole analogues, which may facilitate the penetration through the tumor cell membrane and improve the targeting efficiency. Furthermore, the combined presence of a large conjugated system as well as a three-nitrogen-containing structure make the benzotriazole nucleus more susceptible to binding with enzymes or receptors in biological systems via hydrogen bonds and π-π stacking interactions [ 55 , 56 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structure, Chemical Stability, and In Vitro Cytotoxic Properties of Novel Quinoline-3-Carbaldehyde Hydrazones Bearing a 1,2,4-Triazole or Benzotriazole Moiety

et al. 2018

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A small library of novel quinoline-3-carbaldehyde hydrazones (Series 1), acylhydrazones (Series 2), and arylsulfonylhydrazones (Series 3) bearing either a 1,2,4-triazole or benzotriazole ring at position 2 was prepared, characterized by elemental analyses and IR, NMR, and MS spectra, and then subjected to in vitro cytotoxicity studies on three human tumor cell lines: DAN-G, LCLC-103H, and SISO. In general, compounds 4, 6, and 8 substituted with a 1,2,4-triazole ring proved to be inactive, whereas the benzotriazole-containing quinolines 5, 7, and 9 elicited pronounced cancer cell growth inhibitory effects with IC50 values in the range of 1.23–7.39 µM. The most potent 2-(1H-benzotriazol-1-yl)-3-[2-(pyridin-2-yl)hydrazonomethyl]quinoline (5e) showed a cytostatic effect on the cancer cell lines, whereas N′-[(2-(1H-benzotriazol-1-yl)quinolin-3-yl)methylene]-benzohydrazide (7a) and N′-[(2-1H-benzotriazol-1-yl)quinolin-3-yl)methylene]-naphthalene-2-sulfonohydrazide (9h) exhibited selective activity against the pancreas cancer DAN-G and cervical cancer SISO cell lines. Based on the determined IC50 values, the compound 5e seems to be leading compound for further development as anticancer agent.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Structure, Chemical Stability, and In Vitro Cytotoxic Properties of Novel Quinoline-3-Carbaldehyde Hydrazones Bearing a 1,2,4-Triazole or Benzotriazole Moiety

et al. 2018

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“…Azoles, particularly the benzotriazole nucleus has a key role in both heterocyclic chemistry and medicinal chemistry. − Examples include the extensive use of benzotriazole-based compounds in the treatment of a wide range of diseases, including as anticarcinogenic, , antibacterial and antifungal, − and antimicrobial, antiprotozoal, antiviral, antimycobacterial, and antitubulin agents . Furthermore, it should be noted that benzotriazole scaffolds have stacking interactions because of the conjugated benzene ring structure, which forms hydrogen bonds with a number of enzymes and receptors .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Molecular Docking, and In Vitro Antibacterial Evaluation of Benzotriazole-Based β-Amino Alcohols and Their Corresponding 1,3-Oxazolidines

Singh,

Abrol,

Parihar

et al. 2023

ACS Omega

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In the present study, a series of benzotriazole-based β-amino alcohols were efficiently synthesized in excellent yields via aminolysis of benzotriazolated epoxides under catalyst-and solventfree conditions. Further these β-amino alcohols were successfully utilized to synthesize the corresponding benzotriazole-based oxazolidine heterocyclic derivatives. All the synthesized compounds were characterized by various spectroscopic techniques such as 1 H NMR, 13 C NMR, and mass spectroscopy for structure elucidation. The compounds were subjected to a microtiter plate-based antimicrobial assay. The antimicrobial activity results reveal that the compounds 4a, 4e, and 5f were found to be active against Staphylococcus aureus (ATCC-25923) with minimum inhibitory concentrations (

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“…The action of BTAH in suppressing and controlling Cu degradation is mainly due its strong interaction with the metal surface, predominantly through the nitrogen atoms in the heterocyclic ring (especially when it is in the deprotonated form, BTA – ), as well as the π electrons of the aromatic ring (Figure a). BTAH adsorption results in the formation of supramolecular structures at the Cu surface, which effectively act as a physical barrier to the surrounding environment. − Since its inception, many BTAH derivatives have been synthesized to adapt its use to different conditions, − for example, oil-soluble derivatives are used in the oil and automotive industries to minimize the aforementioned Cu degradation …”

Section: Introductionmentioning

confidence: 99%

Screening the Surface Structure-Dependent Action of a Benzotriazole Derivative on Copper Electrochemistry in a Triple-Phase Nanoscale Environment

Daviddi

Shkirskiy

Kirkman³

et al. 2022

J. Phys. Chem. C

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Copper (Cu) corrosion is a compelling problem in the automotive sector and in oil refinery and transport, where it is mainly caused by the action of acidic aqueous droplets dispersed in an oil phase. Corrosion inhibitors, such as benzotriazole (BTAH) and its derivatives, are widely used to limit such corrosion processes. The efficacy of corrosion inhibitors is expected to be dependent on the surface crystallography of metals exposed to the corrosion environment. Yet, studies of the effect of additives at the local level of the surface crystallographic structure of polycrystalline metals are challenging, particularly lacking for the triple-phase corrosion problem (metal/aqueous/oil). To address this issue, scanning electrochemical cell microscopy (SECCM), is used in an acidic nanodroplet meniscus|oil layer|polycrystalline Cu configuration to explore the grain-dependent influence of an oil soluble BTAH derivative (BTA-R) on Cu electrochemistry within the confines of a local aqueous nanoprobe. Electrochemical maps, collected in the voltammetric mode at an array of >1000 points across the Cu surface, reveal both cathodic (mainly the oxygen reduction reaction) and anodic (Cu electrooxidation) processes, of relevance to corrosion, as a function of the local crystallographic structure, deduced with co-located electron backscatter diffraction (EBSD). BTA-R is active on the whole spectrum of crystallographic orientations analyzed, but there is a complex grain-dependent action, distinct for oxygen reduction and Cu oxidation. The methodology pinpoints the surface structural motifs that facilitate corrosion-related processes and where BTA-R works most efficiently. Combined SECCM–EBSD provides a detailed screen of a spectrum of surface sites, and the results should inform future modeling studies, ultimately contributing to a better inhibitor design.

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Benzotriazole: Much More Than Just Synthetic Heterocyclic Chemistry

Cited by 15 publications

References 101 publications

Synthesis, Structure, Chemical Stability, and In Vitro Cytotoxic Properties of Novel Quinoline-3-Carbaldehyde Hydrazones Bearing a 1,2,4-Triazole or Benzotriazole Moiety

Synthesis, Structure, Chemical Stability, and In Vitro Cytotoxic Properties of Novel Quinoline-3-Carbaldehyde Hydrazones Bearing a 1,2,4-Triazole or Benzotriazole Moiety

Design, Synthesis, Molecular Docking, and In Vitro Antibacterial Evaluation of Benzotriazole-Based β-Amino Alcohols and Their Corresponding 1,3-Oxazolidines

Screening the Surface Structure-Dependent Action of a Benzotriazole Derivative on Copper Electrochemistry in a Triple-Phase Nanoscale Environment

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