848133-17-5

Basic information

• Product Name: 2-Butenamide, N-[4-[[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-3-cyano-7-eth oxy-6-quinolinyl]-4-(dimethylamino)-, (2E)-
• CAS NO: 848133-17-5
• Molecular Formula: C31H29ClFN5O3
• Molecular Weight: 574.054
• Mol File: 848133-17-5.mol

Chemical Properties

• CAS DataBase Reference: 2-Butenamide, N-[4-[[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-3-cyano-7-eth oxy-6-quinolinyl]-4-(dimethylamino)-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butenamide, N-[4-[[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-3-cyano-7-eth oxy-6-quinolinyl]-4-(dimethylamino)-, (2E)-(848133-17-5)
• EPA Substance Registry System: 2-Butenamide, N-[4-[[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-3-cyano-7-eth oxy-6-quinolinyl]-4-(dimethylamino)-, (2E)-(848133-17-5)

Safety Data

• Hazardous Substances Data: 848133-17-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Butenamide, N-[4-[[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-, (2E)is used as a key compound in drug design and development for its potential biological activities. The presence of multiple functional groups allows for various interactions with biological targets, making it a promising candidate for the creation of new medications.
Used in Medicinal Applications:
In the field of medicinal applications, 2-Butenamide, N-[4-[[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-, (2E)is utilized for its potential to contribute to the development of novel therapeutic agents. Its complex structure and functional groups may enable it to target specific biological pathways or receptors, offering new treatment options for various diseases and conditions.

Upstream product

• 848133-14-2 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-amino-7-ethoxyquinoline-3-carbonitrile 
• 202197-26-0 3-chloro-4-(3-fluorobenzyloxy)aniline 
• 214476-09-2 4-Chloro-7-ethoxy-6-nitro-quinoline-3-carbonitrile 
• 99083-25-7 4-bromocrotonyl chloride 
• 124-40-3 dimethyl amine 
• 1056149-69-9 (2E)-(N,N-dimethylamino)-2-butenoyl chloride 

Relevant articles and documents

Methods of synthesizing substituted 3-cyanoquinolines and intermediates thereof

The invention is directed to methods of making substituted 3-cyanoquinolines, including compounds according to the following formula: The methods are amenable to large scale manufacture, avoid the use of chromatographic separations, and provide stable, high purity product more efficiently than in the prior art.

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.

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.

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.