4916-13-6

Basic information

• Product Name: 1-(4-Methoxy-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid
• Synonyms: 1-[(4-Methoxyphenyl)Methyl]-1H-1,2,3-triazole-4-carboxylic acid
• CAS NO: 4916-13-6
• Molecular Formula: C₁₀H₉N₃O₃
• Molecular Weight: 233.22334
• Mol File: 4916-13-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 485.5°C at 760 mmHg
• Flash Point: 247.4°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 3.08E-10mmHg at 25°C
• Refractive Index: 1.623
• CAS DataBase Reference: 1-(4-Methoxy-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Methoxy-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid(4916-13-6)
• EPA Substance Registry System: 1-(4-Methoxy-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid(4916-13-6)

Safety Data

• Hazardous Substances Data: 4916-13-6(Hazardous Substances Data)

Usage

General Description

1-(4-Methoxy-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid is a chemical compound with a structure containing a benzene ring substituted with a methoxy group and linked to a triazole ring by a methylene bridge. It also contains a carboxylic acid functional group. 1-(4-Methoxy-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid has potential applications in medicinal chemistry and drug development, as triazoles are known to exhibit various biological activities, including anti-cancer, antimicrobial, and antifungal properties. The presence of the carboxylic acid group also suggests that this compound may be utilized as a building block in organic synthesis for the preparation of diverse pharmaceutical compounds. Overall, the unique structure of 1-(4-Methoxy-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid makes it a valuable and versatile molecule with potential uses in various fields.

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

• 214541-38-5 1-(4-Methoxy-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid dimethylamide 
• 1422423-72-0 4-(decyloxy)phenyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxylate 
• 1422423-76-4 4-(decyloxy)biphenyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxylate 
• 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 

Relevant articles and documents

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, 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.

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 =