4916-13-6

Usage

Uses

Used in Medicinal Chemistry:
1-(4-Methoxy-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid is used as a pharmaceutical intermediate for the synthesis of various drugs due to its versatile chemical structure and the presence of a carboxylic acid group, which allows for further functionalization and the development of new therapeutic agents.
Used in Drug Development:
In the pharmaceutical industry, 1-(4-Methoxy-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid is utilized as a lead compound for the discovery of new drugs, particularly those targeting cancer, microbial, and fungal infections. Its triazole core and functional groups contribute to its potential as an active pharmaceutical ingredient with therapeutic benefits.
Used in Organic Synthesis:
1-(4-Methoxy-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid serves as a building block in organic synthesis, enabling the preparation of a wide range of pharmaceutical compounds. Its structural features facilitate the creation of diverse molecules with potential applications in various therapeutic areas.
Overall, the unique structure and functional groups of 1-(4-Methoxy-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid make it a valuable and versatile molecule with potential uses in the fields of medicinal chemistry, drug development, and organic synthesis.

InChI:InChI=1/C11H11N3O3/c1-17-9-4-2-8(3-5-9)6-14-7-10(11(15)16)12-13-14/h2-5,7H,6H2,1H3,(H,15,16)

Upstream product

• 910546-48-4 (1-(4-methoxyphenyl)-1H-(1,2,3)triazol-4-yl)methanol 
• 2101-87-3 p-methoxy-phenylazide 
• 471-25-0 Propiolic acid 
• 104-94-9 4-methoxy-aniline 
• 696-62-8 para-iodoanisole 
• 214541-34-1 ethyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxylate 

Downstream Products

• 1609428-56-9 N-(2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethyl)-1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxamide 
• 1609428-44-5 N-(4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)butyl)-1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxamide 
• 68535-49-9 1-(4-methoxyphenyl)-1H-[1,2,3]triazole 
• 1422423-76-4 4-(decyloxy)biphenyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxylate 
• 1422423-72-0 4-(decyloxy)phenyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxylate 
• 214541-38-5 1-(4-Methoxy-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid dimethylamide 

Relevant academic research and scientific papers

Design, Synthesis, and in Vitro and in Vivo Biological Evaluation of Limonin Derivatives for Anti-Inflammation Therapy

In this study, limonin derivatives were used to design new anti-inflammatory compounds with high pharmacological activity and low toxicity. A total of 23 new limonin derivatives were discovered, synthesized, and screened for their anti-inflammatory activity against lipopolysaccharide (LPS)-treated RAW 264.7 cells. Of them, compound f4 was found to be the most active, with a higher efficiency compared with limonin and celecoxib. Subsequently, we studied the mechanism underlying the activity of f4 and found that it inhibited proinflammatory cytokines by blocking the NF-κB/MAPK signaling pathway in LPS-treated RAW 264.7 cells as well as mice. In conclusion, f4 may be a promising anti-inflammatory lead compound.

Synthesis, characterization and thermal stability study of new heterocyclic compounds containing 1,2,3-triazole and 1,3,4-thiadiazole rings

In the current study, a new series of 1,2,3-triazole derivatives was synthesized via copper (I) catalyzed azide-alkyne cycloaddition reaction using a series of synthesised p-substituted phenyl azides and propiolic acid. In addition, a new series of hetero

Synthesis, and evaluation of in vitro and in vivo anticancer activity of 14-substituted oridonin analogs: A novel and potent cell cycle arrest and apoptosis inducer through the p53-MDM2 pathway

A series of novel oridonin derivatives bearing various substituents on the 14-OH position were designed and synthesised. Their antitumour activity was evaluated in vitro against three human cancer cell lines (HCT116, BEL7402, and MCF7). Most tested derivatives showed improved anti-proliferative activity compared to the lead compound oridonin and the positive control drug 5-fluorouracil (5-Fu). Among them, compound C7 (IC50 = 0.16 μM) exhibited the most potent anti-proliferative activity against HCT116 cells; it was about 43- and 155-fold more efficacious than that of oridonin (IC50 = 6.84 μM) and 5-Fu (IC50 = 24.80 μM) in HCT116 cancer cells. Interestingly, the IC50 value of compound C7 in L02 normal cells was 23.6-fold higher than that in HCT116 cells; it exhibited better selective anti-proliferative activity and specificity than oridonin and 5-Fu. Furthermore, compound C7 possibly induced cell cycle arrest and apoptosis by regulating the p53-MDM2 signalling pathway. Notably, C7 displayed more significant suppression of tumour growth than oridonin in colon tumour xenograft models where the tumour growth inhibition rate was 85.82%. Therefore, compound C7 could be a potential lead compound for the development of a novel antitumour agent.

One-Pot Synthesis of 1-Monosubstituted 1,2,3-Triazoles from Propargyl Alcohol

A one-pot synthesis of 1-monosubstituted-1,2,3-triazoles from propargyl alcohol and various aryl azides was achieved. This simple method provides concise and efficient access to various 1-monosubstituted 1,2,3-triazole derivatives through a three-step one

4β-amidotriazole linked podophyllotoxin congeners: DNA topoisomerase-IIα inhibition and potential anticancer agents for prostate cancer

Topoisomerases (topo-I and topo-II) have occupied a significant role in DNA replication, transcription, and are a promising set of antitumor targets. In the present approach, a series of new 4β-amidotriazole linked podophyllotoxin derivatives (10a-i and 1

Towards smart biocide-free anti-biofilm strategies: Click-based synthesis of cinnamide analogues as anti-biofilm compounds against marine bacteria

A set of triazole-based analogues of N-coumaroyltyramine was designed to discover potential leads that may help in the control of bacterial biofilms. the most potent compounds act as inhibitors of biofilm development with EC50 closed to ampicillin (EC50 =

Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ2 receptor ligands

Two novel classes of compounds targeting the sigma-2 (σ2) receptor were synthesized, and their bioactivities to binding σ1 and σ2 receptors were measured. Four novel triazole carboxamide analogues, 24d, 24e, 24f, and 39c, demonstrated high affinity and selectivity for the σ2 receptor. These data suggest 11C-labeled versions of these compounds may be potential σ2-selective radiotracers for imaging the proliferative status of solid tumors.

Synthesis and mesomorphic properties of novel [1,2,3]-triazole mesogenic based compounds

A series of five-membered heterocyclic 1,2,3-triazole derivatives with different substituents in N1 position was synthesized. The heterocyclic moiety was connected through an ester function to a p-decyloxyphenyl or p-decyloxybiphenyl tails Polarized micro

Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids

Herein, the concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied in several classic dipolar [3 + 2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid functionality that can be employed for fur-ther transformations, thereby avoiding prior masking or functionalization. In all cases, BAC provides faster reactions, under milder conditions, with much improved product yields and regioselectivities. In some instances, such as triazole formation from the reaction of azides with 2-alkynoic acids, catalysis with ort/io- nitrophenylboronic acid circumvents the undesirable product decarboxylation observed when using thermal activation. By using NMR spectroscopic studies, the boronic acid catalyst was shown to provide activation by a LUMO-lowering effect in the unsaturated carboxylic acid, likely via a monoacylated hemiboronic ester intermediate.

Synthesis and antibiotic activity of a small molecules library of 1,2,3-triazole derivatives

A small library of simple 1,4-disubstituted 1,2,3-triazoles was prepared using a known one-pot procedure starting from organic halides and terminal alkynes. The compounds were then tested for their antibacterial activity against normal and resistant speci