25351-89-7

Usage

Uses

Used in Pharmaceutical Production:
Acetamide, N-(2-hydroxy-4-nitrophenyl)is used as an intermediate in the synthesis of various pharmaceuticals for its potential to contribute to the development of new drugs. Its unique structural features allow it to be a key component in the creation of molecules with specific therapeutic effects.
Used in Research and Development:
In the scientific community, Acetamide, N-(2-hydroxy-4-nitrophenyl)is utilized in research and development for its potential applications in chemical and biological processes. Researchers explore its properties and reactivity to understand its behavior in different environments and to discover new uses or improve existing ones.
Used in Chemical Processes:
Due to its structural composition, including the presence of a nitro and hydroxy group, Acetamide, N-(2-hydroxy-4-nitrophenyl)may be involved in various chemical reactions, such as esterification, amidation, or other condensation reactions, which are crucial in the synthesis of complex organic molecules.
Used in Biological Research:
Acetamide, N-(2-hydroxy-4-nitrophenyl)-'s potential therapeutic properties make it a candidate for biological research, where it can be studied for interactions with biological systems, such as enzymes or receptors, to explore its possible roles in medicine or as a tool in biological assays.

InChI:InChI=1/C8H8N2O4/c1-5(11)9-7-3-2-6(10(13)14)4-8(7)12/h2-4,12H,1H3,(H,9,11)

Upstream product

• 108-24-7 acetic anhydride 
• 121-88-0 5-Nitro-2-aminophenol 
• 59130-68-6 N,N,O-Triacetyl-2-aminophenol 
• 64-19-7 acetic acid 
• 88-75-5 2-hydroxynitrobenzene 
• 95-55-6 2-amino-phenol 
• 59-49-4 2-Benzoxazolinone 
• 95-21-6 2-methyl-1,3-benzoxazole 
• 5467-64-1 2-acetamidophenyl acetate 
• 75-36-5 acetyl chloride 
• 5683-43-2 2-methyl-6-nitrobenzoxazole 
• 614-80-2 2-(acetylamino)phenol 
• 304667-95-6 2-acetoxy-1-acetylamino-4-nitro-benzene 

Downstream Products

• 66724-79-6 1,4-Bis(2-acetamido-5-nitrophenoxy)butan 
• 848655-78-7 4-acetamido-3-ethoxyaniline 
• 848133-75-5 3-cyano-4-hydroxyl-6-acetamido-7-ethoxyquinoline 
• 848133-76-6 7-ethoxy-6-acetylamino-4-chloro-quinoline-3-carbonitrile 
• 848133-74-4 3-(4-acetamido-3-ethoxyaniline)-2-cyanopropenoic acid ethyl ester 
• 848133-79-9 6-amino-4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylmethoxy)phenylamino]-7-ethoxyquinoline-3-carbonitrile 
• 848133-80-2 6-amino-4-(1-benzenesulfonyl-1H-indol-5-ylamino)-7-ethoxyquinoline-3-carbonitrile 
• 848133-83-5 6-amino-4-(1-benzyl-2,3-dihydro-1H-indol-5-ylamino)-7-ethoxyquinoline-3-carbonitrile 
• 848133-86-8 6-amino-4-[3-chloro-4-(2-chloro-benzyloxy)-phenylamino]-7-ethoxy-quinoline-3-carbonitrile 
• 1026926-78-2 N-{4-[3-chloro-4-(2-chloro-benzyloxy)-phenylamino]-3-cyano-7-ethoxy-quinolin-6-yl}-acetamide 
• 848133-78-8 N-[4-(1-benzenesulfonyl-1H-indol-5-ylamino)-3-cyano-7-ethoxyquinolin-6-yl]acetamide 
• 1025997-45-8 N-[4-(1-benzyl-2,3-dihydro-1H-indol-5-ylamino)-3-cyano-7-ethoxy-quinolin-6-yl]-acetamide 
• 106994-11-0 2-acetamido-5--4-diazocyclohexadien-1-one 
• 106994-23-4 N-(4-Allylamino-3,6-dioxo-cyclohexa-1,4-dienyl)-acetamide 

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.

1 - N - substituted benzyl - 6 - N ' - substituted - 2, 3, 6, 9 - tetrahydro - 1H - [1, 4] oxazino [3, 2 - g] quinoline - 9 - keto - 8 - formic acid class compound and its preparation method and application

The invention belongs to the technical field of medicine compounds, and discloses a 1-N-substituted benzyl-6-N'-substituent-2,3,6,9-tetralin-1H-[1,4] benzoxazine [3,2-g] quinolone-9-ketone-8-formic acid compound and a preparation method and application th

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.

Synthesis and characterization of selected 4,4′-diaminoalkoxyazobenzenes

The role of the -N(CH2CH2OH)2 group in producing a mutagenic response from 4-((3-(2-hydroxyethoxy)4-amino)phenylazo)-N,N-bis(2-hydroxyethyl)aniline has been investigated. To accomplish this goal, a group of substituted 4,4′-diaminoazobenzene dyes was synthesized, and their structures were confirmed using 1H NMR, TOF-LC-ESI mass spectrometry, and combustion analysis. Mutagenicity was determined using the standard Ames test in Salmonella strains TA98, TA100, and TA1538 with and without S9 enzyme activation. The results of this study provide evidence that the mutagenicity of the parent dye arises from the metabolic cleavage of N-hydroxyethyl groups to give the corresponding -NHCH2CH2OH and -NH2 substituted monoazo dyes as direct-acting mutagens. All 5 of the dyes studied were mutagenic at various levels with and without S9 enzyme activation in TA1538. In addition, the results show that removing one N-hydroxyethyl group and capping both -OH groups in the parent dye did not affect mutagenicity, whereas removing both N-hydroxyethyl groups produced a strong direct-acting mutagen in all three bacterial strains. Increasing the length of the N-alkyl chain from two to three carbon atoms eliminated mutagenicity in TA98 without S9 activation.

SUBSTITUTED HETEROCYCLIC COMPOUNDS AS KINASES INHIBITORS AND METHOD OF USE THEREOF

The present invention is directed to novel quinolines and quniazolines, their derivatives, pharmaceutically acceptable salts, solvates and hydrates thereof which are useful for the treatment of protein kinases mediated diseases and conditions. The compounds of this invention have a general Formula (I) wherein R1 to R11 and X are defined herein.

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.