Triazoles

CYP450-mediated mitochondrial ROS production involved in arecoline N-oxide-induced oxidative damage in liver cell lines was written by Wang, Tsu-Shing;Lin, Cheng-Ping;Chen, Yu-Pong;Chao, Mu-Rong;Li, Chien-Chun;Liu, Kai-Li. And the article was included in Environmental Toxicology in 2018.Application In Synthesis of 1H-Benzo[d][1,2,3]triazol-1-amine This article mentions the following:

IARC has classified the betel nut as a human environmental carcinogen. Previous studies have found that arecoline (AR) is the major alkaloid present in the saliva of betel quid chewers. Saliva contains a large content of AR which has been further shown to cause mutation of oral mucosa cells, resulting in oral cancer. Whereas, to date, there are only few studies reported the hepatotoxicity associated with arecoline and betel nut chewing. Therefore, the main purpose of this study was to determine the toxic effects of AR and its oxidative metabolite, arecoline N-oxide (ARNO), in normal liver cell lines. The cytotoxic, genotoxic, and mutagenic effects were detected by crystal violet staining, alk. comet assay, and Salmonella mutagenicity test, resp. Antioxidants, such as N-acetylcysteine, Trolox, and penicillamine, strongly protected liver cells from ARNO-induced DNA damage and ROS production Furthermore, co-treatment with Mito-TEMPO also effectively blocked ARNO-induced ROS production in liver cells. Besides antioxidants, co-treatment with 1-aminobenzotriazole and methimazole nearly completely suppressed ARNO-induced ROS production in liver cells. Our data suggest that arecoline ingested from the habit of chewing betel quid can be primarily oxidized to ARNO, thereby enhancing its toxicity through increased ROS production Collectively, our results provide novel cellular evidence for the pos. connection between habitual betel quid chewing and the risk for liver damage. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6Application In Synthesis of 1H-Benzo[d][1,2,3]triazol-1-amine).

1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6) belongs to triazole derivatives. Triazoles are important five-member nitrogen heterocycles involved in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners, as well as biologically active agents. The presence of the three nitrogen atoms in triazole structures afforded opportunities for a plethora of structural modification with the generation of novel therapeutically potential agents, which is different from other heterocyclic compounds.Application In Synthesis of 1H-Benzo[d][1,2,3]triazol-1-amine

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Diazo aldehyde chemistry. Part 3. synthesis of 4-acyl-1H-1,2,3-triazole derivatives was written by Sezer, Oezkan;Dabak, Kadir;Akar, Ahmet;Anac, Olcay. And the article was included in Helvetica Chimica Acta in 1996.Computed Properties of C5H7N3O2 This article mentions the following:

Ten α-diazo-β-oxo aldehydes were condensed with PhNH₂, NH₃, NH₂OH, and NH₂CONHNH₂ to yield 1-substituted 4-acyl-1H-1,2,3-triazoles in moderate to good yields. The method is simple and regiospecific. Thus, it is superior to the widely used acylacetylene and azide approach. In the experiment, the researchers used many compounds, for example, Ethyl 1H-1,2,3-triazole-5-carboxylate (cas: 40594-98-7Computed Properties of C5H7N3O2).

Ethyl 1H-1,2,3-triazole-5-carboxylate (cas: 40594-98-7) belongs to triazole derivatives. Triazoles are important five-member nitrogen heterocycles involved in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners, as well as biologically active agents. Due to the structural characteristics, both 1,2,3- and 1,2,4-triazoles are able to accommodate a broad range of substituents (electrophiles and nucleophiles) around the core structures and pave the way for the construction of diverse novel bioactive molecules.Computed Properties of C5H7N3O2

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Methoxsalen as an in vitro phenotyping tool in comparison with 1-aminobenzotriazole was written by Palacharla, Raghava Choudary;Molgara, Parusharamulu;Panthangi, Hanumanth Rao;Boggavarapu, Rajesh Kumar;Manoharan, Arun Kumar;Ponnamaneni, Ranjith Kumar;Ajjala, Devender Reddy;Nirogi, Ramakrishna. And the article was included in Xenobiotica in 2019.Category: triazoles This article mentions the following:

The objective is to evaluate methoxsalen as an in vitro phenotyping tool in comparison to ABT as a nonspecific inactivator of P 450 mediated metabolism The reversible inhibition of methoxsalen and ABT against the P 450, FMO, AO, MAO-A and -B, enzymes were evaluated using standard marker probe reactions. The time-dependent inhibition of P 450 enzymes was evaluated in human liver microsomes. CES1 activities were determined by monitoring the depletion of known substrate, the clopidogrel. The metabolism of P 450 substrates in the presence and absence of methoxsalen or ABT was evaluated in human liver microsomes. Methoxsalen is a direct inhibitor and inhibited the activities (>90%) of all enzymes at a concentration of 300μM except for CYP2C9. Methoxsalen is also a potent time-dependent inhibitor of all P 450 enzymes except for CYP2C19 (moderate) at a concentration of 300μM. Methoxsalen inhibited the metabolism of P 450 substrates in the pre-incubation mode. ABT is a potent TDI of several P 450 except for CYP2C19 (47%) and CYP2C9 (27%). The results indicate that methoxsalen is a potent pan P 450 inhibitor than ABT and can be a better tool in distinguishing P 450 mediated metabolism form non-P 450 metabolism in human liver microsomes. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6Category: triazoles).

1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6) belongs to triazole derivatives. Triazoles consist of a five-membered ring containing three nitrogen atoms and are biologically active, especially as antifungal, antimicrobial and enzyme inhibitors. 1,2,3-Triazoles are usually prepared following (3+2) cycloaddition protocols. A common technique for unsubstituted triazoles is the Huisgen azide-alkyne 1,3-dipolar cycloaddition: a azide and an alkyne react at high temperature to form a ring. However, the Huisgen strategy produces a mixture of isomers (typically 1,4- and 1,5-disubstituted) when used to produce substituted triazoles.Category: triazoles

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Rapid and selective detection of aluminum ion using 1,2,3-triazole-4,5-dicarboxylic acid-functionalized gold nanoparticle-based colorimetric sensor was written by Zhao, Shengliang;Chen, Liqiong;Liu, Feiyan;Fan, Yongyao;Liu, Yiheng;Han, Yulai;Hu, Yunfei;Su, Jingyun;Song, Chunyan. And the article was included in RSC Advances in 2021.Recommanded Product: 1H-1,2,3-Triazole-4,5-dicarboxylic acid This article mentions the following:

A highly selective, sensitive, rapid, low-cost, simple and visual colorimetric system for Al³⁺ ion detection was developed based on gold nanoparticles (AuNPs) modified with 1,2,3-triazole-4,5-dicarboxylic acid (TADA). The modified gold nanoparticles (TADA-AuNPs) were first prepared by sodium citrate (Na₃Ct) reduction of chloroauric acid (HAuCl₄) and then capped with a TADA ligand. Five TADA-AuNPs sensors were constructed with sodium citrate (Na₃Ct)/chloroauric acid (HAuCl₄) under different molar ratios. Results showed that the molar ratio of Na₃Ct/HAuCl₄, TADA-AuNPs concentration, pH range and detection time had obvious influences on the performance of this colorimetric method. The optimal detection conditions for Al³⁺ ions were as follows: Na₃Ct/HAuCl₄ molar ratio of 6.4 : 1, 0.1 mM of TADA-AuNPs concentration, 4-10 pH range and 90 s of detection time. Under the optimal conditions and using di-Ph carbazone (DPC) as a Cr³⁺ masking agent, this colorimetric sensor exhibited outstanding time efficiency, selectivity and sensitivity for Al³⁺ detection. In particular, the detection limits of this sensor obtained via UV-vis and the naked eye were 15 nM and 1.5μM, resp., which were much lower than the current limit (3.7μM) for drinking water in WHO regulation and better than the previous reports. Moreover, this colorimetric sensing system could be used to for on-site, trace level and real-time rapid detection of Al³⁺ in real water samples. In the experiment, the researchers used many compounds, for example, 1H-1,2,3-Triazole-4,5-dicarboxylic acid (cas: 4546-95-6Recommanded Product: 1H-1,2,3-Triazole-4,5-dicarboxylic acid).

1H-1,2,3-Triazole-4,5-dicarboxylic acid (cas: 4546-95-6) belongs to triazole derivatives. Triazoles are important five-member nitrogen heterocycles involved in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners, as well as biologically active agents.Triazole heterocyclic structures are found to form many weak nonbond interactions with the receptors and enzymes in biological systems.Recommanded Product: 1H-1,2,3-Triazole-4,5-dicarboxylic acid

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Transport-metabolism interplay of atazanavir in rat hepatocytes was written by Nicolaie, Johan;De Bruyn, Tom;Thevelin, Louise;Augustijns, Patrick;Annaert, Pieter. And the article was included in Drug Metabolism & Disposition in 2016.Application of 1614-12-6 This article mentions the following:

The aim of this study was to explore the mechanisms governing the intra- to extracellular unbound concentration ratio (Kpu,u) for the HIV protease inhibitor atazanavir (ATV) in rat hepatocytes. We had previously proposed a new method to determine Kpu,u by using the unbound Km values from metabolism studies with suspended rat hepatocytes and rat liver microsomes. Following that method, we determined that the value of ATV Kpu,u was 0.32, indicating that ATV hepatocellular clearance is uptake rate-limited. This hypothesis was supported by the linear correlation between Kpu,u and active uptake clearance (P = 0.04; R²=0.82) in the presence of increasing concentrations of the uptake transport inhibitor losartan. Moreover, in contrast to an expected increase of Kpu,u upon inhibition of ATV metabolism, a decrease of Kpu,u was observed, suggesting an increased impact of sinusoidal efflux. In summary, involvement of active uptake transport does not guarantee high intracellular accumulation; however, it has a key role in regulating intracellular drug concentrations and drug metabolism These findings will help improve future in vitro-to-in vivo extrapolations and likewise physiol. based pharmacokinetic models. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6Application of 1614-12-6).

1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6) belongs to triazole derivatives. The many free lone pairs in triazoles make them useful as coordination compounds, although not typically as haptic ligands. Triazole growth retardants such as uniconazole and paclobutrazol have been known to inhibit the biosynthesis of gibberellins by blocking kaurene oxidase, an P450 enzymeApplication of 1614-12-6

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A luminescent novel octanuclear silver(I) cluster framework with potential Cr₂O₇^2- sensing was written by Jin, Jun-Cheng;Jiang, Chen;Chang, Wen-Gui;Xu, Guang-Nian;Fu, Xu-Cheng. And the article was included in Inorganic Chemistry Communications in 2016.Recommanded Product: 1H-1,2,3-Triazole-4,5-dicarboxylic acid This article mentions the following:

An unique and novel octanuclear silver(I) cluster compound, [Ag₈(ADC)₄]_n (1) (H₂ADC = 1,3-adamantanedicarboxylic acid), was synthesized and characterized. Compound 1 exhibits significant Ag-Ag interactions to form 2-dimensional infinite silver layers with multiple unsaturated Ag atoms. Also, Luminescent studies show that 1 can exhibit highly selective response to Cr₂O₇^2- through luminescence quenching effect in aqueous solution, which make its good candidate as luminescent sensor. In the experiment, the researchers used many compounds, for example, 1H-1,2,3-Triazole-4,5-dicarboxylic acid (cas: 4546-95-6Recommanded Product: 1H-1,2,3-Triazole-4,5-dicarboxylic acid).

1H-1,2,3-Triazole-4,5-dicarboxylic acid (cas: 4546-95-6) belongs to triazole derivatives. The many free lone pairs in triazoles make them useful as coordination compounds, although not typically as haptic ligands. Both the triazoles and their derivatives have significant biological properties including antimicrobial, antiviral, antitubercular, anticancer, anticonvulsant, analgesic, antioxidant, anti-inflammatory, and antidepressant activities.Recommanded Product: 1H-1,2,3-Triazole-4,5-dicarboxylic acid

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Three New cpt-Metal Complexes Displaying 0D, 1D, and 3D Topology Structures was written by Song, Jiang-Feng;Zhou, Rui-Sha;Zhang, Jia;Xu, Chun-Yan;Li, Yan-Bing;Wang, Biao-Bing. And the article was included in Zeitschrift fuer Anorganische und Allgemeine Chemie in 2011.Recommanded Product: 4-(4H-1,2,4-Triazol-4-yl)benzoic acid This article mentions the following:

Three new cpt-metal complexes of different topol. structures were synthesized by solvothermal methods (Hcpt = 4-(4-carboxyphenyl)-1,2,4-triazole). The structure of [Mn(cpt)₂·2H₂O] (1) is essentially 0-dimensional monomeric, but extended into a 2-dimensional supramol. network through crosslinking hydrogen bonds. In [Cu(cpt)(OH)·2H₂O]·2H₂O (2), the hydroxo groups as well as cpt ligands join the copper ions into an infinite polymeric [Cu(μ-cpt)(μ-OH)] chain, which is interconnected into a 3-dimensional supramol. network with different oriented channels by 1-dimensional water chains. [Zn(cpt)₂]·0.5DMF·CH₃CH₂OH (3), which crystallizes in a 3-dimensional open framework with 4-fold interpenetrated diamondoid network topol., represents the 1st 3-dimensional structure based on cpt anions. The structure differences demonstrate that the reaction metal ions have an important effect on the structures of these complexes. In the experiment, the researchers used many compounds, for example, 4-(4H-1,2,4-Triazol-4-yl)benzoic acid (cas: 157069-48-2Recommanded Product: 4-(4H-1,2,4-Triazol-4-yl)benzoic acid).

4-(4H-1,2,4-Triazol-4-yl)benzoic acid (cas: 157069-48-2) belongs to triazole derivatives. Triazoles are important five-member nitrogen heterocycles involved in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners, as well as biologically active agents. The presence of the three nitrogen atoms in triazole structures afforded opportunities for a plethora of structural modification with the generation of novel therapeutically potential agents, which is different from other heterocyclic compounds.Recommanded Product: 4-(4H-1,2,4-Triazol-4-yl)benzoic acid

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Catalytic asymmetric electrochemical α-arylation of cyclic β-ketocarbonyls with anodic benzyne intermediates was written by Zhang, Qinglin;Guo, Chang. And the article was included in Youji Huaxue in 2020.Quality Control of 1H-Benzo[d][1,2,3]triazol-1-amine This article mentions the following:

This achieved the use of electrochem. methods to generate highly active benzyne or cyclohexyne intermediates, cleverly combined cobalt acetate with benzyne or cyclohexyne intermediates, improved the stability of the phenylyne intermediates, and successfully combined with cyclic β-ketocarbonyl compound activated by the chiral primary amine catalyst developed by the research group, and realized the synthesis of various high enantioselective α-aryl and α-cyclohexenyl derivatives In the experiment, the researchers used many compounds, for example, 1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6Quality Control of 1H-Benzo[d][1,2,3]triazol-1-amine).

1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6) belongs to triazole derivatives. Among the nitrogen-containing heterocyclic compounds, triazoles emerge with superior pharmacological applications. Triazole growth retardants such as uniconazole and paclobutrazol have been known to inhibit the biosynthesis of gibberellins by blocking kaurene oxidase, an P450 enzymeQuality Control of 1H-Benzo[d][1,2,3]triazol-1-amine

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Triazolyl, Imidazolyl, and Carboxylic Acid Moieties in the Design of Molybdenum Trioxide Hybrids: Photophysical and Catalytic Behavior was written by Lysenko, Andrey B.;Senchyk, Ganna A.;Domasevitch, Konstantin V.;Kobalz, Merten;Krautscheid, Harald;Cichos, Jakub;Karbowiak, Miroslaw;Neves, Patricia;Valente, Anabela A.;Goncalves, Isabel S.. And the article was included in Inorganic Chemistry in 2017.Application In Synthesis of 4-(4H-1,2,4-Triazol-4-yl)benzoic acid This article mentions the following:

Three organic ligands bearing 1,2,4-triazolyl donor moieties, (S)-4-(1-phenylpropyl)-1,2,4-triazole (trethbz), 4-(1,2,4-triazol-4-yl)benzoic acid (trPhCO₂H), and 3-(1H-imidazol-4-yl)-2-(1,2,4-triazol-4-yl)propionic acid (trhis), were prepared to evaluate their coordination behavior in the development of Mo(VI) oxide organic hybrids. Four compounds, [Mo₂O₆(trethbz)₂]·H₂O (1), [Mo₄O₁₂(trPhCO₂H)₂]·0.5H₂O (2a), [Mo₄O₁₂(trPhCO₂H)₂]·H₂O (2b), and [Mo₈O₂₅(trhis)₂(trhisH)₂]·2H₂O (3), were synthesized and characterized. The monofunctional tr-ligand gave a zigzag chain [Mo₂O₆(trethbz)₂] built up from cis-{MoO₄N₂} octahedra united through common μ₂-O vertexes. Employing the heterodonor ligand with tr/-CO₂H functions afforded either layer or ribbon structures of corner- or edge-sharing {MoO₅N} polyhedra (2a or 2b) stapled by tr-links in axial positions, whereas -CO₂H groups remained uncoordinated. The presence of the imidazole-heterocycle as an extra function in trhis facilitated formation of zwitterionic mols. with a protonated imidazolium group (imH⁺) and a neg. charged -CO₂^– group, whereas the tr-fragment was left neutral. Under the acidic hydrothermal conditions used, the organic ligand binds to Mo atoms either through [N-N]-tr or through both [N-N]-tr and μ₂-CO₂^– units, which occur in protonated bidentate or zwitterionic tetradentate forms (trhisH⁺ and trhis, resp.). This leads to a new zigzag subtopol. motif (3) of neg. charged polyoxomolybdate {Mo₈O₂₅}_n^2n- consisting of corner- and edge-sharing cis-{MoO₄N₂} and {MoO₆} octahedra, while the tetradentate zwitterionic trhis species connect these chains into a 2D net. Electronic spectra of the compounds showed optical gaps consistent with semiconducting behavior. The compounds were studied as epoxidation catalysts via the model reactions of achiral and prochiral olefins (cis-cyclooctene and trans-β-methylstyrene) with tert-Bu hydroperoxide. The best-performing catalyst (1) was explored for the epoxidation of other olefins, including biomass-derived Me oleate, Me linoleate, and prochiral DL-limonene. In the experiment, the researchers used many compounds, for example, 4-(4H-1,2,4-Triazol-4-yl)benzoic acid (cas: 157069-48-2Application In Synthesis of 4-(4H-1,2,4-Triazol-4-yl)benzoic acid).

4-(4H-1,2,4-Triazol-4-yl)benzoic acid (cas: 157069-48-2) belongs to triazole derivatives. The many free lone pairs in triazoles make them useful as coordination compounds, although not typically as haptic ligands. 1,2,3-Triazoles are usually prepared following (3+2) cycloaddition protocols. A common technique for unsubstituted triazoles is the Huisgen azide-alkyne 1,3-dipolar cycloaddition: a azide and an alkyne react at high temperature to form a ring. However, the Huisgen strategy produces a mixture of isomers (typically 1,4- and 1,5-disubstituted) when used to produce substituted triazoles.Application In Synthesis of 4-(4H-1,2,4-Triazol-4-yl)benzoic acid

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Convulsant effects of abused synthetic cannabinoids JWH-018 and 5F-AB-PINACA are mediated by agonist actions at CB1 receptors in mice was written by Wilson, Catheryn D.;Tai, Sherrica;Ewing, Laura;Crane, Jasmine;Lockhart, Taylor;Fujiwara, Ryochi;Radominska-Pandya, Anna;Fantegrossi, William E.. And the article was included in Journal of Pharmacology and Experimental Therapeutics in 2019.Synthetic Route of C6H6N4 This article mentions the following:

Convulsant effects of abused synthetic cannabinoid (SCB) drugs have been reported in humans and laboratory animals, but the mechanism of these effects is not known. We compared convulsant effects of partial CB1R agonist Δ9-tetrahydrocannabinol (THC), full CB1R agonist SCBs JWH-018 and 5F-ABPINACA, and classic chem. convulsant pentylenetetrazol (PTZ) using an observational rating scale in mice. THC did not elicit convulsions, but both SCBs did so as effectively as and more potently than PTZ. SCB-elicited convulsions were attenuated by the CB1R antagonist rimonabant or by THC, or by dose regimens of THC and JWH-018, which downregulate and desensitize CB1Rs. None of these treatments altered the convulsant effects of PTZ, although diazepam attenuated PTZelicited convulsions without altering SCB-induced convulsant effects. Repeated administration of a subthreshold dose of PTZ kindled convulsant effects, but this was not observed with the SCBs, and no cross-kindling was observed Repeated administration of the SCBs resulted in tolerance to convulsant effects, but no cross-tolerance to PTZ was observed Inhibition on Phase I metabolism via nonselective inhibition of CYP450s with 1-aminobenzotriazole potentiated the hypothermic effects of the SCBs and protected against the convulsant effects of JWH-018, but not those of 5F-AB-PINACA or PTZ. Incubation of human liver microsomes with the SCBs showed that JWH-018 is eliminated via oxidation, whereas 5F-ABPINACA is not. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6Synthetic Route of C6H6N4).

1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6) belongs to triazole derivatives. The many free lone pairs in triazoles make them useful as coordination compounds, although not typically as haptic ligands. Triazole growth retardants such as uniconazole and paclobutrazol have been known to inhibit the biosynthesis of gibberellins by blocking kaurene oxidase, an P450 enzymeSynthetic Route of C6H6N4

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics