3213-80-7

Usage

Uses

Used in Organic Synthesis:
2-Phenyl-2H-1,2,3-triazole-4-carbaldehyde is used as a building block in the synthesis of heterocyclic compounds, which are important in various chemical and pharmaceutical applications due to their unique properties and structures.
Used in Pharmaceutical Research:
2-Phenyl-2H-1,2,3-triazole-4-carbaldehyde is utilized in the development of new pharmaceuticals, particularly for its antimicrobial and antitumor properties. Its ability to exhibit these biological activities makes it a valuable candidate for the treatment of various diseases and conditions.
Used in Analytical Chemistry:
2-Phenyl-2H-1,2,3-triazole-4-carbaldehyde is employed in the development of fluorescent probes for the detection of metal ions. This application is crucial in environmental monitoring, medical diagnostics, and other fields where the sensitive and selective detection of metal ions is required.
Used in Chemical Research:
2-Phenyl-2H-1,2,3-triazole-4-carbaldehyde is also used in chemical research to explore its reactivity and potential applications in the synthesis of new materials and compounds, further expanding its utility in the scientific community.

InChI:InChI=1/C9H7N3O/c13-7-8-6-10-12(11-8)9-4-2-1-3-5-9/h1-7H

Upstream product

• 6206-85-5 (E)-2-phenyl-2H-1,2,3-triazole-4-carbaldehyde oxime 
• 15476-07-0 L_r-1cat_F-(2-phenyl-2H-[1,2,3]triazol-4-yl)-butane-1t_F,2c_F,3r_F-triol 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 6341-06-6 2-phenyl-4-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-2H-1,2,3-triazole 
• 7732-18-5 water 
• 849021-50-7 trifluoro-N'-(2-phenyl-2H-1,2,3-triazol-4-yl-carbonyl)methanesulfonic hydrazide 
• 62289-79-6 methyl 2-phenyl-2H-1,2,3-triazole-4-carboxylate 
• 50-00-0 formaldehyd 
• 4343-71-9 1H-[1,2,3]triazole-4-carbaldehyde 
• 46994-10-9 4-(D-xylo-tetritol-1-yl)-2-phenyl-2H-1,2,3-triazole 
• 14575-41-8 1-(2-phenyl-2H-1,2,3-triazol-4-yl)butane-1,2,3,4-tetraol 
• 100-63-0 phenylhydrazine 
• 18615-48-0 L-arabino-6-deoxy-[2]hexosulose-bis-phenylhydrazone 

Downstream Products

• 3359-24-8 2-(2-phenyl-2H-1,2,3-triazole-4-yl)methanol 
• 13306-99-5 2-phenyl-2H-[1,2,3]triazole-4-carboxylic acid 
• 6206-87-7 3-(2-phenyl-2H-[1,2,3]triazol-4-yl)-acrylic acid 
• 6207-31-4 (2E)-1-phenyl-3-(2-phenyl-2H-1,2,3-triazol-4-yl)prop-2-en-1-one 
• 69366-69-4 2,5-dihydro-3,4-dihydroxy-2-(2-phenyl-1,2,3-triazol-4-yl)-5-imino-5(2H)-furanone 
• 83741-68-8 (S)-6-((S)-1,2-Dihydroxy-ethyl)-2-(2-phenyl-2H-[1,2,3]triazol-4-yl)-1,2,3,6-tetrahydro-furo[3,4-d]imidazol-4-one 
• 6206-87-7 3-(2-Phenyl-2H-1,2,3-triazol-4-yl)-2-propenoic acid 
• 99410-68-1 (E)-3-Methyl-4-(2-phenyl-2H-[1,2,3]triazol-4-yl)-but-3-en-2-one 
• 99410-69-2 (E)-3-Phenyl-4-(2-phenyl-2H-[1,2,3]triazol-4-yl)-but-3-en-2-one 

Relevant academic research and scientific papers

A fine-tuned lipophilicity/hydrophilicity ratio governs antibacterial potency and selectivity of bifurcated halogen bond-forming nbtis

Herein, we report the design of a focused library of novel bacterial topoisomerase inhibitors (NBTIs) based on innovative mainly monocyclic right-hand side fragments active against DNA gyrase and Topo IV. They exhibit a very potent and wide range of antibacterial activity, even against some of the most concerning hard-to-treat pathogens for which new antibacterials are urgently needed, as reported by the WHO and CDC. NBTIs enzyme activity and whole cell potency seems to depend on the fine-tuned lipophilicity/hydrophilicity ratio that governs the permeability of those compounds through the bacterial membranes. Lipophilicity of NBTIs is apparently optimal for passing through the membrane of Gram-positive bacteria, but the higher, although not excessive lipophilicity and suitable hydrophilicity seems to determine the passage through Gram-negative bacterial membranes. However, due to the considerable hERG inhibition, which is still at least two orders of magnitude away from MICs, continued optimization is required to realize their full potential.

Trifluoromethanesulfonic hydrazides

We succeeded to observe at low temperature in reactions of trifluoromethanesulfonic anhydride and trifluoromethanesulfonyl chloride with hydrazine, phenyl hydrazine, and 1,1-dimethylhydrazine a formation of the corresponding trifluoromethanesulfonic hydra

Synthesis and evaluation of novel 1-(((6-substitutedbenzo[d]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents

To discover new agrochemicals with prominent pesticidal properties, a series of novel β-naphthol derivatives containing benzothiazolylamino and various heteroaryl groups (8a-q) were efficiently synthesised via Betti reaction. The bioassay results showed t

Naphthol derivatives containing benzothiazolamide and heteroaryl groups and preparation method and application thereof

The invention relates to naphthol derivatives containing benzothiazolamide and heteroaryl groups and a preparation method and application thereof. A compound obtained by reacting naphthol, heteroaromatic aldehyde and benzothiazolamide is shown as a genera

1-Aryl-1H- and 2-aryl-2H-1,2,3-triazole derivatives blockade P2X7 receptor in?vitro and inflammatory response in?vivo

Fifty-one 1,2,3-triazole derivatives were synthesized and evaluated with respect to P2X7 receptor (P2X7R) activity and its associated pore. These triazoles were screened in vitro for dye uptake assay and its cytotoxicity against mammalian cell types. Seven 1,2,3-triazole derivatives (5e, 6e, 8h, 9d, 9i, 11, and 12) potently blocked P2X7 receptor pore formation in vitro (J774.G8 cells and peritoneal macrophages). All blockers displayed IC50 value inferior to 500 nM, and they have low toxicity in either cell types. These seven selected triazoles inhibited P2X7R mediated interleukin-1 (IL-1β) release. In particular, compound 9d was the most potent P2X7R blocker. Additionally, in mouse acute models of inflammatory responses induced by ATP or carrageenan administration in the paw, compound 9d promoted a potent blocking response. Similarly, 9d also reduced mouse LPS-induced pleurisy cellularity. In silico predictions indicate this molecule appropriate to develop an anti-inflammatory agent when it was compared to commercial analogs. Electrophysiological studies suggest a competitive mechanism of action of 9d to block P2X7 receptor. Molecular docking was performed on the ATP binding site in order to observe the preferential interaction pose, indicating that binding mode of the 9d is by interacting its 1,2,3-triazole and ether moiety with positively charged residues and with its chlorobenzene moiety orientated toward the apolar end of the ATP binding site which are mainly composed by the Ile170, Trp167 and Leu309 residues from α subunit. These results highlight 9d derivative as a drug candidate with potential therapeutic application based on P2X7 receptor blockade.

Synthesis and Fungicidal Activities of Novel 1,2,4-Triazole Thione Derivatives Containing 1,2,3-Triazole and Substituted Piperazine Moieties

A series of novel 1,2,4-triazole thione derivatives containing 1,2,3-triazole and substituted piperazine moieties were synthesized via the Mannich reaction of 1,2,3-triazole-containing 1,2,4-triazole thiol intermediates with various substituted piperazines and formaldehyde in high yields. The structures of 14 title compounds were confirmed by melting points, IR, 1H NMR, 13C NMR, and elemental analysis. The bioassay results showed that some of the title compounds exhibit significant fungicidal activities against several plant fungi at 50 μg/mL, especially trifluoromethyl-containing triazole thione derivative 9g showed broad activities and could be made further structural optimization for novel fungicides innovation research.

Palladium-catalyzed ortho-alkoxylation of 2-aryl-1,2,3-triazoles

Palladium-catalyzed alkoxylation of 2-aryl-1,2,3-triazoles was described in the presence of various groups in the aromatic rings. In addition, some other directing groups of heterocycles containing nitrogen were explored.

An easy arylation of 2-substituted 1,2,3-triazoles

A selective, efficient and catalytic ligand-free method for the direct arylation of 2-aryl-1,2,3-triazoles via Pd-catalyzed C-H bond activation is described. The process smoothly proceeds in moderate to excellent yields. This journal is the Partner Organisations 2014.

1-Phenyl-1H- and 2-phenyl-2H-1,2,3-triazol derivatives: Design, synthesis and inhibitory effect on alpha-glycosidases

Due to aging and increasingly overweight in human population, the incidence of non-insulin dependent diabetes mellitus (NIDDM or Type 2 DM) is increasing considerably. Therefore, searching for new α-glycosidase inhibitors (GIs) capable of slowing down carbohydrate assimilation by humans is an important strategy towards control of NIDDM. In this report, we disclose the search for new easily accessible synthetic triazoles as anti-diabetic compounds. Two series of non-glycosid triazoles were synthesized (series A and B) and screened against baker's yeast α-glucosidase (MAL12) and porcine pancreatic α-amylase activity (PPA). Of the 60 compounds tested at 500 μM, were considered hits (≥60% inhibition) six triazoles against MAL12 and three against PPA, with the inhibition reaching up to 99.4% on MAL12 and 88.6% on PPA. The IC50 values were calculated for both enzymes and ranged from 54 to 482 μM for MAL12 and 145 to 282 μM for PPA. These results demonstrated the potential activity of simple and non-glycosidic triazoles as an important novel class of GIs for the development of drugs to treat Type 2 DM.

Synthesis and structure-activity relationships of antitubercular 2-nitroimidazooxazines bearing heterocyclic side chains

Recently described biphenyl analogues of the antituberculosis drug PA-824 displayed improved potencies against M. tuberculosis but were poorly soluble. Heterobiaryl analogues of these, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility. The compounds were constructed by coupling the chiral 2-nitroimidazooxazine alcohol with various halomethyl-substituted arylheterocycles, by cycloadditions to a propargyl ether derivative of this alcohol, or by Suzuki couplings on haloheterocyclic methyl ether derivatives. The arylheterocyclic compounds were all more hydrophilic than their corresponding biphenyl analogues, and several showed solubility improvements. 1-Methylpyrazole, 1,3-linked-pyrazole, 2,4-linked-triazole, and tetrazole analogues had 3- to 7-fold higher MIC potencies against replicating M. tb than predicted by their lipophilicities. Two pyrazole analogues were >10-fold more efficacious than the parent drug in a mouse model of acute M. tb infection, and one displayed a 2-fold higher solubility. 2009 American Chemical Society.