20442-96-0

Basic information

• Product Name: methyl 4-azidobenzoate
• Synonyms: Benzoic acid, 4-azido-, methyl ester
• CAS NO: 20442-96-0
• Molecular Formula: C₈H₇N₃O₂
• Molecular Weight: 177.1601
• Mol File: 20442-96-0.mol
• Article Data: 45

Chemical Properties

• CAS DataBase Reference: methyl 4-azidobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-azidobenzoate(20442-96-0)
• EPA Substance Registry System: methyl 4-azidobenzoate(20442-96-0)

Safety Data

• Hazardous Substances Data: 20442-96-0(Hazardous Substances Data)

Upstream product

• 619-45-4 4-methoxycarbonyl aniline 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 122-04-3 4-nitro-benzoyl chloride 
• 171364-80-0 methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 1174501-32-6 4-(methoxycarbonyl)phenylboronic acid 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 150-13-0 4-amino-benzoic acid 
• 67-56-1 methanol 
• 6427-66-3 4-azidobenzoic acid 

Downstream Products

• 1402046-06-3 4-[5-[[(pyridin-2-ylmethyl)amino]methyl][1,2,3]triazol-1-yl]benzoic acid methyl ester 
• 1402045-94-6 4-[5-[(benzoyl-pyridin-2-ylmethylamino)methyl][1,2,3]triazol-1-yl]benzoic acid methyl ester 
• 1437656-46-6 4,4'-diethynyl-2,2'-bipyridine 
• 874-90-8 4-methoxybenzonitrile 
• 619-45-4 4-methoxycarbonyl aniline 
• 5320-91-2 4,4'-bismethoxycarbonylazobenzene 
• 1380227-21-3 methyl 4-(4-(2-morpholino-4-oxo-1,4-dihydroquinolin-8-yl)-1H-1,2,3-triazol-1-yl)benzoate 

Relevant articles and documents

Structural modification of the aryl sulfonate ester of cjoc42 for enhanced gankyrin binding and anti-cancer activity

Gankyrin is an oncogenic protein involved in various biological processes, such as cellular growth and proliferation. Its overexpression in certain cancers results in an increase of gankyrin-mediated protein-protein interactions (PPIs), leading to cancer proliferation. To date, only one small molecule (cjoc42) has been identified to bind gankyrin, which simultaneously inhibits its interaction with the 26S proteasome. Despite this advance, 2nd generation inhibitors are needed to improve gankyrin binding and cellular efficacy. To this end, an extensive SAR for the aryl sulfonate ester moiety of the cjoc42 scaffold was explored, and showed that substitutions at the 2-, 3-, and 4-positions manifested significant increases in gankyrin binding, resulting in the most potent binders of gankyrin to date. Subsequent cell-based assay evaluation of our derivatives demonstrated antiproliferative activity against pediatric liver cancer cell lines Hep3B and HepG2, which was not previously observed for cjoc42.

White-Light Emission from Dual-Way Photon Energy Conversion in a Dye-Encapsulated Metal–Organic Framework

The design of white-light phosphors is attractive in solid-state lighting (SSL) and related fields. A new strategy in obtaining white light emission (WLE) from dual-way photon energy conversion in a series of dye?MOF (LIFM-WZ-6) systems is presented. Besi

Benzimidazole–galactosides bind selectively to the Galectin-8 N-Terminal domain: Structure-based design and optimisation

We have obtained the X-ray crystal structure of the galectin-8 N-terminal domain (galectin-8N) with a previously reported quinoline–galactoside ligand at a resolution of 1.6 ?. Based on this X-ray structure, a collection of galactosides derivatised at O3 with triazole, benzimidazole, benzothiazole, and benzoxazole moieties were designed and synthesised. This led to the discovery of a 3-O-(N-methylbenzimidazolylmethyl)–galactoside with a Kd of 1.8 μM for galectin-8N, the most potent selective synthetic galectin-8N ligand to date. Molecular dynamics simulations showed that benzimidazole–galactoside derivatives bind the non-conserved amino acid Gln47, accounting for the higher selectivity for galectin-8N. Galectin-8 is a carbohydrate-binding protein that plays a key role in pathological lymphangiogenesis, modulation of the immune system, and autophagy. Thus, the benzimidazole-derivatised galactosides represent promising compounds for studies of the pathological implications of galectin-8, as well as a starting point for the development of anti-tumour and anti-inflammatory therapeutics targeting galectin-8.

Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO)

Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO), which mediate kynurenine pathway of tryptophan degradation, have emerged as potential new targets in immunotherapy for treatment of cancer because of their critical role in immunosuppression in the tumor microenvironment. In this investigation, we report the structural optimization and structure-activity relationship studies of 1-phenyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as a new class of IDO1/TDO dual inhibitors. Among all the obtained dual inhibitors, 1-(3-chloro-4-fluorophenyl)-6-fluoro-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione (38) displayed the most potent IDO1 and TDO inhibitory activities with IC50 (half-maximal inhibitory concentration) values of 5 nM for IDO1 and 4 nM for TDO. It turned out that compound 38 was not a PAINS compound. Compound 38 could efficiently inhibit the biofunction of IDO1 and TDO in intact cells. In LL2 (Lewis lung cancer) and Hepa1-6 (hepatic carcinoma) allograft mouse models, this compound also showed considerable in vivo anti-tumor activity and no obvious toxicity was observed. Therefore, 38 could be a good lead compound for cancer immunotherapy and deserving further investigation.