848133-74-4

Basic information

• Product Name: 2-PROPENOIC ACID, 3-[[4-(ACETYLAMINO)-3-ETHOXYPHENYL]AMINO]-2-CYANO-, ETHYL ESTER
• Synonyms: 2-PROPENOIC ACID, 3-[[4-(ACETYLAMINO)-3-ETHOXYPHENYL]AMINO]-2-CYANO-, ETHYL ESTER;3-[[4-(ACETYLAMINO)-3-ETHOXYPHENYL]AMINO]-2-CYANO-2-PROPENOIC ACID ETHYL ESTER;2-Propenoic acid, 3-[[4-(acetylamino)-3-;ethoxyphenyl]amino]-2-cyano-,ethyl ester;N-(4-(2,2-dicyanovinylaMino)-2-ethoxyphenyl)acetaMide;ethyl (Z)-3-((4-acetamido-3-ethoxyphenyl)amino)-2-cyanoacrylate;STFJATKWKPLWME-ZRDIBKRKSA-N;Ethyl 3-((4-acetamido-3-ethoxyphenyl)amino)-2-cyanoacrylate
• CAS NO: 848133-74-4
• Molecular Formula: C₁₆H₁₉N₃O₄
• Molecular Weight: 317.34
• Mol File: 848133-74-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 496.1 °C at 760 mmHg
• Flash Point: 253.8 °C
• Appearance: /
• Density: 1.243 g/cm³
• Vapor Pressure: 5.56E-10mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: 2-PROPENOIC ACID, 3-[[4-(ACETYLAMINO)-3-ETHOXYPHENYL]AMINO]-2-CYANO-, ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PROPENOIC ACID, 3-[[4-(ACETYLAMINO)-3-ETHOXYPHENYL]AMINO]-2-CYANO-, ETHYL ESTER(848133-74-4)
• EPA Substance Registry System: 2-PROPENOIC ACID, 3-[[4-(ACETYLAMINO)-3-ETHOXYPHENYL]AMINO]-2-CYANO-, ETHYL ESTER(848133-74-4)

Safety Data

• Hazardous Substances Data: 848133-74-4(Hazardous Substances Data)

Usage

General Description

2-Propenoic acid, 3-[[4-(acetylamino)-3-ethoxyphenyl]amino]-2-cyano-, ethyl ester is a chemical compound with a complex structure. It consists of a propenoic acid (acrylic acid) backbone with an ethyl ester functional group and a cyano group attached to the third carbon atom. Additionally, it contains a complex aromatic amine group with an acetylamine substituent and an ethoxy group. 2-PROPENOIC ACID, 3-[[4-(ACETYLAMINO)-3-ETHOXYPHENYL]AMINO]-2-CYANO-, ETHYL ESTER has potential applications in various industries, including pharmaceuticals, polymers, and organic synthesis, due to its unique structure and functional groups. However, it is essential to handle this chemical with caution as it may pose hazards to human health and the environment.

InChI:InChI=1/C16H19N3O4/c1-4-22-15-8-13(6-7-14(15)19-11(3)20)18-10-12(9-17)16(21)23-5-2/h6-8,10,18H,4-5H2,1-3H3,(H,19,20)/b12-10+

Upstream product

• 42466-67-1 ethyl (ethoxymethylene)cyanoacetate 
• 848655-78-7 4-acetamido-3-ethoxyaniline 
• 94-05-3 ethyl (ethoxymethylene)cyanoacetate 
• 144918-37-6 1-cyano-1-ethoxycarbonyl-1-butene 
• 121-88-0 5-Nitro-2-aminophenol 
• 116496-76-5 4-acetamido-3-ethoxynitrobenzene 
• 25351-89-7 N-(2-hydroxy-4-nitrophenyl)acetamide 

Downstream Products

• 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 
• 1360430-63-2 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)acrylamide 

Relevant articles and documents

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.

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.