116496-76-5

Usage

Uses

Used in Organic Synthesis:
4-ACETAMIDO-3-ETHOXYNITROBENZENE is used as a precursor in organic synthesis for the production of various organic compounds. The presence of the nitro group makes it a valuable starting material for the synthesis of a range of derivatives through reduction or other chemical reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-ACETAMIDO-3-ETHOXYNITROBENZENE is used as a building block for the development of new drugs. The acetamide and ethoxy groups provide additional functionality that can be exploited to create molecules with specific biological activities, making it a promising candidate for the design of novel therapeutic agents.
Used in Agrochemical Industry:
4-ACETAMIDO-3-ETHOXYNITROBENZENE is also utilized in the agrochemical industry as a starting material for the synthesis of pesticides and other agrochemicals. Its unique structure allows for the development of compounds with targeted pest control properties, contributing to more effective and environmentally friendly agricultural practices.
Used in Materials Science:
In the field of materials science, 4-ACETAMIDO-3-ETHOXYNITROBENZENE is used as a component in the development of new materials with specific properties. The versatility of its structure allows for the creation of materials with tailored characteristics, such as improved stability, reactivity, or other desirable attributes for various applications.
Overall, 4-ACETAMIDO-3-ETHOXYNITROBENZENE is a multifaceted chemical compound with a broad range of potential uses across different industries, thanks to its unique structural features and the ability to serve as a precursor for the synthesis of other compounds.

InChI:InChI=1/C10H12N2O4/c1-3-16-10-6-8(12(14)15)4-5-9(10)11-7(2)13/h4-6H,3H2,1-2H3,(H,11,13)

Upstream product

• 581-08-8 2'-ethoxyacetanilide 
• 74-96-4 ethyl bromide 
• 25351-89-7 N-(2-hydroxy-4-nitrophenyl)acetamide 
• 94-70-2 ortho-phenitidine 
• 121-88-0 5-Nitro-2-aminophenol 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 

Downstream Products

• 848655-78-7 4-acetamido-3-ethoxyaniline 
• 1201080-09-2 N-(3-cyano-7-ethoxy-4-oxo-1,4-dihydroquinolin-6-yl)acetamide 
• 361162-95-0 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile 
• 915941-95-6 N-(4-[3-chloro-4-(pyridin-2-ylmethoxy)phenylamino]-3-cyano-7-ethoxyquinoline-6-yl)acetamide 
• 1233953-82-6 3-chloro-N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)propanamide 
• 848139-78-6 6-amino-4-[[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino]-7-ethoxyquinoline-3-carbonitrile 
• 1360430-68-7 N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-morpholinopropanamide 
• 1233953-83-7 N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-piperidin-1-ylpropanamide 
• 1233953-81-5 N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-(dimethylamino)propanamide 
• 1360430-67-6 N-(4-((3-chloro-4-(pyridin-2-ylmethoxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)acrylamide 
• 1360430-66-5 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-morpholinopropanamide 
• 1360430-65-4 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-piperidin-1-ylpropanamide 
• 1360430-72-3 3-chloro-N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)propanamide 
• 1360430-64-3 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-(dimethylamino)propanamide 

Relevant academic research and scientific papers

Design, synthesis and biological study of potent and covalent HER-2 tyrosine kinase inhibitors with low cytotoxicity in vitro

The discovery and development of a novel HER-2 tyrosine kinase inhibitor for the treatment of HER2-positive breast cancer are presented in this article. EGFR family has been recognized as a crucial meditator in the cancer progression; HER-2 tyrosine kinase was one of the members among them. In the effort to explore potent HER-2 inhibitors, a novel series of 4-anilino-3-cyanoquinoline derivatives have been designed, synthesized and evaluated. Most compounds possessed modest proliferation inhibition on SK-BR-3 cell line and HER-2 kinase. Compound 16 appeared to be the most potent compound (HER-2 kinase IC50: 19.4?nM, SK-BR-3 IC50: 94?nM). In the experiment of cellular cytotoxicity assay, compound 16 shows a much lower cytotoxicity than neratinib on Beas-2b cell line (Human bronchial epithelial cells). In conclusion, compound 16 would be a promising lead compound for further anti-breast cancer drug discovery.

Irreversible inhibition of epidermal growth factor receptor activity by 3-aminopropanamides

Irreversible epidermal growth factor receptor (EGFR) inhibitors contain a reactive warhead which covalently interacts with a conserved cysteine residue in the kinase domain. The acrylamide fragment, a commonly employed warhead, effectively alkylates Cys797 of EGFR, but its reactivity can cause rapid metabolic deactivation or nonspecific reactions with off-targets. We describe here a new series of irreversible inhibitors containing a 3-aminopropanamide linked in position 6 to 4-anilinoquinazoline or 4-anilinoquinoline-3- carbonitrile driving portions. Some of these compounds proved to be as efficient as their acrylamide analogues in inhibiting EGFR-TK (TK = tyrosine kinase) autophosphorylation in A549 lung cancer cells. Moreover, several 3-aminopropanamides suppressed proliferation of gefitinib-resistant H1975 cells, harboring the T790M mutation in EGFR, at significantly lower concentrations than did gefitinib. A prototypical compound, N-(4-(3-bromoanilino)quinazolin-6- yl)-3-(dimethylamino)propanamide (5), did not show covalent binding to cell-free EGFR-TK in a fluorescence assay, while it underwent selective activation in the intracellular environment, releasing an acrylamide derivative which can react with thiol groups.

Synthesis of n-(3-cyano-7-ethoxy-1,4-dihydro-4-oxoquinolin-6-yl)acetamide

New route for the preparation of N-(3-cyano-7-ethoxy-1,4-dihydro-4- oxoquinolin-6-yl)acetamide (1), a key intermediate for the synthesis of selective EGFR kinase inhibitors, was described.

Optimization of 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitriles as orally active, irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity

A series of new 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitrile derivatives that function as irreversible inhibitors of human epidermal growth factor receptor-2 (HER-2) and epidermal growth factor receptor (EGFR) kinases have been prepared. These compounds demonstrated enhanced activities for inhibiting HER-2 kinase and the growth of HER-2 positive cells compared to our EGFR kinase inhibitor 86 (EKB-569). Three synthetic routes were used to prepare these compounds. They were prepared mostly by acylation of 6-amino-4-(arylamino) quinoline-3-carbonitriles with unsaturated acid chlorides or by amination of 4-chloro-6-(crotonamido)-quinoline-3-carbonitriles with monocyclic or bicyclic anilines. The third route was developed to prepare a key intermediate, 6-acetamido-4-chloroquinoline-3-carbonitrile, that involved a safer cyclization step. We show that attaching a large lipophilic group at the para position of the 4-(arylamino) ring results in improved potency for inhibiting HER-2 kinase. We also show the importance of a basic dialkylamino group at the end of the Michael acceptor for activity, due to intramolecular catalysis of the Michael addition. This, along with improved water solubility, resulted in compounds with enhanced biological properties. We present molecular modeling results consistent with the proposed mechanism of inhibition. Binding studies of one compound, 25o (C-14 radiolabeled), showed that it binds irreversibly to HER-2 protein in BT474 cells. Furthermore, it demonstrated excellent oral activity, especially in HER-2 overexpressing xenografts. Compound 25o (HKI-272) was selected for further studies and is currently in phase I clinical trials for the treatment of cancer.

Process for the synthesis of 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile

The present invention provides a process for the preparation of 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile comprising the steps and products disclosed within this application.

Protein tyrosine kinase enzyme inhibitors

This invention provides compounds of formula 1, having the structure wherein R1, R2, R3, R4, and R5 are described within the specification.

SUBSTITUTED QUINOLINES AS PROTEIN TYROSINE KINASE ENZYME INHIBITORS

This invention provides compounds of formula (I), having the structure wherein R1, R2, R3 are described within the specification. The compounds act as anti-cancer agents by inhibition of HER-2 and EGFR.