220699-88-7

Basic information

• Product Name: N-[4-[(3-Bromophenyl)amino]-6-quinazolinyl]-3(E)-chloro-2-propenamide
• Synonyms: N-[4-[(3-Bromophenyl)amino]-6-quinazolinyl]-3(E)-chloro-2-propenamide
• CAS NO: 220699-88-7
• Molecular Weight: 403.665
• Mol File: 220699-88-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-[4-[(3-Bromophenyl)amino]-6-quinazolinyl]-3(E)-chloro-2-propenamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-[(3-Bromophenyl)amino]-6-quinazolinyl]-3(E)-chloro-2-propenamide(220699-88-7)
• EPA Substance Registry System: N-[4-[(3-Bromophenyl)amino]-6-quinazolinyl]-3(E)-chloro-2-propenamide(220699-88-7)

Safety Data

• Hazardous Substances Data: 220699-88-7(Hazardous Substances Data)

Upstream product

• 10342-97-9 N,N-diisopropylmethylamine 
• 169205-78-1 6-amino-4-[(3-bromophenyl)amino]quinazoline 
• 3721-35-5 (Z)-3-chloroacryloyl chloride 
• 169205-77-0 6-nitro-4-(3-bromophenylaniline)quinazoline 
• 3721-36-6 (E)-3-Chloroacryloyl chloride 

Relevant articles and documents

SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS TYROSINE KINASE INHIBITORS

This invention provides compounds of formula (1) wherein X is C3-7 cycloalkyl, pyridinyl, pyrimidinyl or phenyl ring optionally substituted as described in claim 1, R1, R3 and R4 are chosen from the groups listed in claim 1. R2 is chosen from various unsaturated acyl groups listed in claim 1, with certain compounds being disclaimed. Use as tyrosine kinase inhibitors for the treatment of cancer and certain kidney diseases such as polycystic kidney disease.

6-Substituted-4-(3-bromophenylamino)quinazolines as putative irreversible inhibitors of the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases with enhanced antitumor activity

A series of new 6-substituted-4-(3-bromophenylamino)quinazoline derivatives that may function as irreversible inhibitors of epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases have been prepared. These inhibitors have, at the C-6 position, butynamide, crotonamide, and methacrylamide Michael acceptors bearing water-solublilizing substituents. These compounds were prepared by acylation of 6-amino-4-(3-bromophenylamino)quinazoline with unsaturated acid chlorides or mixed anhydrides. We show that attaching a basic functional group onto the Michael acceptor results in greater reactivity, due to intramolecular catalysis of the Michael addition and/or an inductive effect of the protonated basic group. This, along with improved water solubility, results in compounds with enhanced biological properties. We present molecular modeling and experimental evidence that these inhibitors interact covalently with the target enzymes. One compound, 16a, was shown to have excellent oral activity in a human epidermoid carcinoma (A431) xenograft model in nude mice.