848655-77-6

Basic information

• Product Name: N-(4-((3-Chloro-4-fluorophenyl)aMino)-3-cyano-7-ethoxyquinolin-6-yl)acetaMide
• Synonyms: N-(4-((3-Chloro-4-fluorophenyl)aMino)-3-cyano-7-ethoxyquinolin-6-yl)acetaMide;N-[4-[(3-Chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxy-6-quinolinyl]acetamide;N-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl]acetamide
• CAS NO: 848655-77-6
• Molecular Formula: C₂₀H₁₆ClFN₄O₂
• Molecular Weight: 398.8180432
• Mol File: 848655-77-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 590.591°C at 760 mmHg
• Flash Point: 310.978°C
• Appearance: /
• Density: 1.403g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.652
• CAS DataBase Reference: N-(4-((3-Chloro-4-fluorophenyl)aMino)-3-cyano-7-ethoxyquinolin-6-yl)acetaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-((3-Chloro-4-fluorophenyl)aMino)-3-cyano-7-ethoxyquinolin-6-yl)acetaMide(848655-77-6)
• EPA Substance Registry System: N-(4-((3-Chloro-4-fluorophenyl)aMino)-3-cyano-7-ethoxyquinolin-6-yl)acetaMide(848655-77-6)

Safety Data

• Hazardous Substances Data: 848655-77-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H16ClFN4O2/c1-3-28-19-8-17-14(7-18(19)25-11(2)27)20(12(9-23)10-24-17)26-13-4-5-16(22)15(21)6-13/h4-8,10H,3H2,1-2H3,(H,24,26)(H,25,27)

Upstream product

• 1201080-09-2 N-(3-cyano-7-ethoxy-4-oxo-1,4-dihydroquinolin-6-yl)acetamide 
• 367-21-5 3-chloro-4-fluorophenylamine 
• 848133-76-6 7-ethoxy-6-acetylamino-4-chloro-quinoline-3-carbonitrile 
• 25351-89-7 N-(2-hydroxy-4-nitrophenyl)acetamide 
• 116496-76-5 4-acetamido-3-ethoxynitrobenzene 
• 121-88-0 5-Nitro-2-aminophenol 
• 848655-78-7 4-acetamido-3-ethoxyaniline 
• 848133-74-4 3-(4-acetamido-3-ethoxyaniline)-2-cyanopropenoic acid ethyl ester 

Downstream Products

• 1245710-99-9 N-[4-(3-chloro-4-fluorophenylamino)-3-cyano-7-hydroxyquinolin-6-yl]-acetamide 
• 1360430-63-2 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)acrylamide 
• 1360430-64-3 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-(dimethylamino)propanamide 
• 1360430-72-3 3-chloro-N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)propanamide 
• 1360430-65-4 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-piperidin-1-ylpropanamide 
• 1360430-66-5 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-morpholinopropanamide 
• 361162-95-0 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile 
• 1245711-03-8 (E)-4-methylamino-but-2-enoic acid [4-(3-chloro-4-fluorophenylamino)-3-cyano-7-(2-fluoroethoxy)-quinolin-6-yl]-amide hydrochloride 
• 1245711-01-6 6-amino-4-(3-chloro-4-fluorophenylamino)-7-(2-fluoroethoxy)-quinoline-3-carbonitrile 
• 1313378-65-2 N-[4-(3-chloro-4-fluorophenylamino)-3-cyano-7-(2-fluoro-ethoxy)-quinolin-6-yl]-acetamide 
• 1263388-96-0 {(E)-3-[4-(3-chloro-4-fluorophenylamino)-3-cyano-7-(2-fluoroethoxy)-quinolin-6-ylcarbamoyl]-allyl}-methylcarbamic acid tert-butyl ester 

Relevant articles and documents

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.