89521-54-0

Basic information

• Product Name: Benzenamine, 2-nitro-6-(phenylmethoxy)-
• CAS NO: 89521-54-0
• Molecular Formula: C13H12N2O3
• Molecular Weight: 244.25
• Mol File: 89521-54-0.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: Benzenamine, 2-nitro-6-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 2-nitro-6-(phenylmethoxy)-(89521-54-0)
• EPA Substance Registry System: Benzenamine, 2-nitro-6-(phenylmethoxy)-(89521-54-0)

Safety Data

• Hazardous Substances Data: 89521-54-0(Hazardous Substances Data)

Upstream product

• 603-85-0 2-Amino-3-nitrophenol 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 89521-55-1 3-phenylmethoxybenzene-1,2-diamine 
• 1799974-69-8 (3S)-3-(7-methoxy-1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-methyl-3-(((R)-4-methyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)phenyl)propanoic acid 

Relevant articles and documents

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Harnessing the E3 Ligase KEAP1 for Targeted Protein Degradation

Proteolysis targeting chimeras (PROTACs) represent a new class of promising therapeutic modalities. PROTACs hijack E3 ligases and the ubiquitin-proteasome system (UPS), leading to selective degradation of the target proteins. However, only a very limited number of E3 ligases have been leveraged to generate effective PROTACs. Herein, we report that the KEAP1 E3 ligase can be harnessed for targeted protein degradation utilizing a highly selective, noncovalent small-molecule KEAP1 binder. We generated a proof-of-concept PROTAC, MS83, by linking the KEAP1 ligand to a BRD4/3/2 binder. MS83 effectively reduces protein levels of BRD4 and BRD3, but not BRD2, in cells in a concentration-, time-, KEAP1- and UPS-dependent manner. Interestingly, MS83 degrades BRD4/3 more durably than the CRBN-recruiting PROTAC dBET1 in MDA-MB-468 cells and selectively degrades BRD4 short isoform over long isoform in MDA-MB-231 cells. It also displays improved antiproliferative activity than dBET1. Overall, our study expands the limited toolbox for targeted protein degradation.

Synthesis method of 4-(benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carboxylic acid

The invention discloses a synthesis method of 4-(benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carboxylic acid, and belongs to the field of synthesis of fine chemical intermediates. The method comprisesthe following six steps: 1, reacting 2-amino-3-nitrophenol serving as a raw material with benzyl chloride under the action of inorganic base to obtain an intermediate (I); 2, reacting the intermediate(I) with N-chlorosuccinimide to obtain 2-benzyloxy-4-chloro-6-nitroaniline (II); 3, carrying out an acylation reaction on the intermediate (II) and acetic anhydride to obtain N-(2-benzyloxy-4-chloro-6-nitro-phenyl)acetamide (III); 4, dissolving the intermediate (III) and dimethylformamide to obtain 4-acetamido-3-benzyloxy-5-nitrobenzamide (IV) under the catalysis of CuI; 5, carrying out a cyclization reaction on the intermediate (IV) to obtain 7-benzyloxy-2-methyl-3H-benzimidazole-5-carboxylic acid amide (V); and 6, carrying out a hydrolysis reaction on the intermediate (V) and a potassium hydroxide solution to obtain the 4-(benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carboxylic acid (VI). The method has the advantages of accessible raw materials, low price, simple preparation method, mildreaction conditions and low equipment requirements, and is suitable for industrial production.