56436-25-0

Usage

Common uses

Production of pharmaceuticals, dyes, and polymers

Chemical structure

Derivative of benzene-1,2-diamine with a methoxyethyl group attached to the nitrogen atom

Potential applications

Corrosion inhibitor and component in the synthesis of novel materials

Suitability

Suitable for various industrial and research purposes

Importance

Important building block in the development of new chemical compounds with useful applications.

Upstream product

• 56436-24-9 N-[2-(methyloxy)ethyl]-2-nitroaniline 
• 1493-27-2 ortho-nitrofluorobenzene 
• 109-85-3 2-methoxyethylamine 
• 25186-42-9 N-isopropyl-2-nitroaniline 
• 13534-98-0 3-bromopyridin-4-amine 
• 95-54-5 1,2-diamino-benzene 
• 6482-24-2 2-Bromoethyl methyl ether 
• 88-73-3 2-Chloronitrobenzene 

Downstream Products

• 405211-51-0 1-(2-Methoxy-ethyl)-1H-benzoimidazol-2-ol 
• 1259838-44-2 methyl 4-(1-(2-methoxyethyl)-1H-benzo[d]imidazol-2-ylamino)benzoate 
• 405211-51-0 1-(2-methoxyethyl)-1H-benzo[d]imidazol-2(3H)-one 

Relevant academic research and scientific papers

Discovery of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as novel and potent bromodomain and extra-terminal (BET) inhibitors with anticancer efficacy

As epigenetic readers, bromodomain and extra-terminal domain (BET) family proteins bind to acetylated-lysine residues in histones and recruit protein complexes to promote transcription initiation and elongation. Inhibition of BET bromodomains by small molecule inhibitors has emerged as a promising therapeutic strategy for cancer. Herein, we describe our efforts toward the discovery of a novel series of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as BET inhibitors. Intensive structural modifications led to the identification of compound 35f as the most active inhibitor of BET BRD4 with selectivity against BET family proteins. Further biological studies revealed that compound 35f can arrest the cell cycle in G0/G1 phase and induce apoptosis via decreasing the expression of c-Myc and other proteins related to cell cycle and apoptosis. More importantly, compound 35f showed favorable pharmacokinetic properties and antitumor efficacy in MV4-11 mouse xenograft model with acceptable tolerability. These results indicated that BET inhibitors could be potentially used to treat hematologic malignancies and some solid tumors.

Cell-Based Drug Discovery: Identification and Optimization of Small Molecules that Reduce c-MYC Protein Levels in Cells

Elevated expression of the c-MYC oncogene is one of the most common abnormalities in human cancers. Unfortunately, efforts to identify pharmacological inhibitors that directly target MYC have not yet yielded a drug-like molecule due to the lack of any known small molecule binding pocket in the protein, which could be exploited to disrupt MYC function. We have recently described a strategy to target MYC indirectly, where a screening effort designed to identify compounds that can rapidly decrease endogenous c-MYC protein levels in a MYC-amplified cell line led to the discovery of a compound series that phenocopies c-MYC knockdown by siRNA. Herein, we describe our medicinal chemistry program that led to the discovery of potent, orally bioavailable c-MYC-reducing compounds. The development of a minimum pharmacophore model based on empirical structure activity relationship as well as the property-based approach used to modulate pharmacokinetics properties will be highlighted.

TREX1 INHIBITORS AND USES THEREOF

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds for inhibiting three prime repair exonuclease 1 ("TREX1").

Diversity-Oriented Synthesis of Coumarin-Linked Benzimidazoles via a One-Pot, Three-Step, Intramolecular Knoevenagel Cyclization

Diversity-oriented synthesis of coumarin-linked benzimidazoles from N-(2-aminophenyl)-2-cyanoacetamide was achieved via a one-pot, three-step sequential reaction in excellent yields. In situ intramolecular cyclization of the cyanoacetamide afforded benzimidazoles which subsequently underwent a Knoevenagel condensation of the 2-cyanomethylbenzimidazoles with salicylaldehydes promoted by triethylamine to reach the target compounds. An important intermediate, 2-(2-imino-2H-chromen-3-yl)-1H-benzimidazole was characterized by X-ray analysis and further hydrolyzed to 2-(coumarin-3-yl)benzimidazole in acidic condition. Among the synthesized compounds, some were found to be promising inhibitors of porcine kidney d-amino acid oxidase (pkDAO).

Rapid construction of imidazopyridines from ortho-haloaminopyridines

A practical strategy for the preparation of imidazopyridine derivatives from ortho-haloaminopyridines utilizing a two-step C-N coupling/cyclization reaction sequence has been developed. This procedure provides rapid and efficient access to many medicinally interesting imidazopyridine compounds and related imidazopyrazine/purine heterocycles.

Copper catalyzed aerobic oxidative cyclization and ketonization: One pot synthesis of benzoimidazo[1,2-: A] imidazolones

A highly efficient synthesis of benzoimidazo[1,2-a]imidazolone through a novel oxidative 5-exo-dig cyclization-ketonization cascade of 2-aminobenzimidazole, aldehyde and terminal alkyne has been explored under aerobic conditions. The reaction proceeds thr

Renin inhibitors

The invention relates to compounds having the formulae: wherein the variables are as defined herein. The invention further relates to methods of making and using these compounds, and pharmaceutical compositions, kits and articles of manufacture comprise the compounds.

IMIDAZOLYL-IMIDAZOLES AS KINASE INHIBITORS

Disclosed are compounds having the formula: wherein R1A, R1B, R2 and R3 are as defined herein, and methods of making and using the same.

BENZAMIDE DERIVATIVES

Disclosed are benzamide derivatives useful in slowing the expansion of cancer cells.

Synthesis and structure-activity relationship of new piperidinyl and piperazinyl derivatives as antiallergics

A series of piperazinebenzothiazoles 3-5, piperazinebenzimidazoles 6-12, piperidinobenzothiazoles 14-45, piperidinobenzoxazoles 46-52 and piperidinobenzimidazoles 53-129 has been synthesized and their antiallergic activity evaluated by means of the passive cutaneous anaphylaxis (PCA) assay. Structure-activity relationships are discussed and related to classical antihistaminics. Piperidino derivatives with an aryl group linked to the nitrogen atom by an ethyl chain are the most active compounds, with ID50 1 mg/kg po. Some of these compounds are more potent antiallergics than astemizole and terfenadine.